Transgender Narratives and Online Dating: Reframing Trans-Cis Relations (in Cape Town)

Elana Leah Ryklief*, Sally Ann Murray

Corresponding author: Elana Leah Ryklief, Department of English, Stellenbosch University, Stellenbosch, South Africa, elanaryklief@gmail.com

DOI: https://doi.org/10.5130/pjmis.v21i1-2.9929

Article History: Received 23/07/2025; Accepted 24/12/2025; Published 19/02/2026

Abstract

The recent inclusivity and protection of transgender identities on online dating platforms have improved the creation, dissemination, and reception of individualised transgender narratives, making both sites and trans narratives more accessible and acceptable to (potentially) transamorous cis men. Yet within research, trans–cis dating relations remain largely unexplored, and existing studies (Smith 2007; Doozy 2021) have tended to pathologise such relationships and attractions. Using an autoethnographic lens grounded in my lived experience, this article shows how transgender narratives on online dating platforms are personalised and shaped through question-and-answer exchanges and the nuanced re-telling of transitioning.

I challenge dominant assumptions about dating a transgender woman in Cape Town, South Africa, including hyper-sexualised portrayals of trans women as sex workers, an emphasis on sexual fetishes, and the idea of habitually multiple and temporary sexual encounters. While my own experiences of online dating have been tumultuous, I argue that these platforms have generative potential to shift, for the better, the wider reception of unconventional transgender narratives. They enable the circulation of diverse transgender stories that unsettle stereotypical and normative assumptions about trans lives and trans dating. My analysis draws on an understanding of transitioning narratives as existing within a liminal, ongoing, and processual space, rather than a linear teleology of a ‘pre-’ and ‘post-transition’. Hil Malatino conceptualises this as the trans interregnum, defined by ‘moments during transition […] that do not have a definite end’, and as a space that dispels the ‘cruel optimism’ attached to medicalised notions of transition (Malatino 2019: 635). Within this framework, online dating platforms emerge as important sites for communicating the complexity of transgender experience and for fostering what Malatino describes as ‘creative and caring acts of trans intimacy’ (Malatino 2019: 635), particularly in encounters with cis men who may be unfamiliar with trans lives.

Keywords

Transgender Narratives; Trans Life Writing; Trans Intimacies; Online Dating; Trans-Cis Relationships; Transamory

Online dating has significant potential to expand and improve the creation, dissemination, and reception of narratives about trans life. I engage with this premise by examining key elements of online dating, including the stereotypical, hyper-sexualised interpretations that cis men often project onto trans women in Cape Town, South Africa, and my own efforts to reconfigure these expectations and assert my agency as a trans woman. As Webster et al. argue, safety, inclusivity, acceptance, and affirmation in online dating can ‘provide a nurturing environment in which [trans] people can explore their identity’ (Webster et al. 2025: 13). At the same time, although dating apps are ‘imbued with normative sexual ideologies’, they also create opportunities for cis users to encounter and engage with alternative gender identities, including trans identities (Junck 2024: 92).

Currently, there is little to no research on how, why, and for what purposes trans women use dating apps. This article aims to address this gap by sharing and critically reflecting on my own experience as a trans woman using online dating apps to find and date cis men in Cape Town. First, I discuss and contextualise my experience of using dating apps while being Coloured, trans, and living on the Cape Flats. Secondly, I expand on the reasons why trans women use dating apps. Thirdly, I examine some of the positive aspects of online dating and show how, as a trans app user, I have used these platforms to challenge and reframe dominant narratives about trans women. Finally, I briefly reflect on the romantic relationships I formed and explore how I subverted binary power dynamics in trans–cis relationships that originated online. In this article, I adopt a blended approach, combining autoethnographic accounts of online and offline dating with relevant scholarship and theory, to explore how the sharing of alternative trans narratives online can act as a conduit and mediator for the growing understanding and acceptance of diverse trans experiences.

Within the South African context, ‘being trans, especially visibly so, is dangerous’ and comes with its own difficulties (Tomson 2016: 159). Monakali and Francis note that in ‘South African society, where gender-based violence and sexual violence against women and femme-presenting individuals are endemic’, the malevolent treatment of women, especially trans women, is reflected in online spaces (2020: 12). There are many documented accounts of the violence and the social and medical issues trans women face (Kukard 2024; Van der Merwe et al. 2023; Camminga 2019), although my own process of trans becoming, with emotional assistance from my mother and help from the public health sector, spared me from some of the violence, prejudice, and dangers that trans women in South Africa can face. When it comes to online dating, however, such dangers can re-materialise, owing to society’s unpredictable attitudes towards trans people. As the autoethnographic elements of this article suggest, the online dating scene in Cape Town is shaped by and dependent on the social, cultural, and personal desires of cisgender men. However, I also seek to signal the more generative possibilities of the online dating environment for trans experience and for the broader understanding of what it means to be trans.

My purpose for using online dating apps changed over the years. At first, I used the apps to ‘hook up’ with and meet new men in the Cape Town area. Primarily, these encounters served my need for sex and provided me with an escape from my dismal and (covertly) abusive home environment. Upon reflection, during my doctoral research, I began to understand that I had traded my body and sex for brief moments of safety and distance from the violence I faced and witnessed at home. I had not realised that ‘the more sex I had with strangers, the more sex became my secret release […], a way to feel less alone’, while also providing me with ‘a place to put my emotions’ (Bergdorf 2023: 47–50). Even later in my research process, I realised that this exchange was another act of violence I had imposed on myself. Like Janet Mock, in her memoir Redefining Realness, I had mistakenly thought that ‘being promiscuous helped me establish a sense of control over the pain and turmoil I was dealing with at home and with myself, my body, and my identity’ (Mock 2014: 173).

I found partners on older dating apps, such as MXit and 2go, which had chatrooms that catered to queer individuals. Later, I started using apps such as Grindr and Badoo, which had quickly amassed more users and become popular. These apps enabled me to access men who were closer to my home on the Cape Flats, increasing the likelihood of partner suitability and shaping my experience of seeking intimacy. Still, the sexual activities I engaged in were transactional and helped construct the ‘rules, norms, aberrations and limits of [my] sexual behaviour’ (Masullo & Coppola 2021: 325). For a while, this was a pattern my life followed: chat online, have sex with strangers, then forget them. Given my personal and social circumstances, in the formative years of my transition, experiences of trans intimacy were fleeting, or even ‘fugitive’, meaning not merely brief, but also associated with a fearful need for concealment (Lubinsky & Aultman 2024: 404). I wanted more. I wanted fulfilling, emotionally mature trans–cis relationships, and sex, but this prospect seemed far-fetched and unattainable on the dating apps I used at the time. In retrospect, my own actions, and the fact that I played into the desires of cis men, hindered my ability to meet my own emotional needs and shaped how intimate meanings were communicated (Smithee 2021: 4).

Before actively transitioning, I was less conscious of how online dating could benefit me and my identity development. Later, as I became more self-aware during my transition, I realised that some of the benefits of transitioning, according to research, might include ‘improved relationships, emergence of support, passing privilege, and improved awareness of social issues’ (Motter & Softas-Nall 2021). I used my critical understanding of these benefits to inform and transform my use of online dating. As I have discovered by connecting autoethnographic elements of lived experience with more conventional scholarly investigation, there are many purposes for using dating apps. Among these are: ‘accessing the sexual market’ (Masullo & Coppola 2021: 329), seeking relationships and platforms that cater to personal needs (Griffiths and Armstrong 2024: 122–127), creating safe, inclusive spaces and making connections (Brooker et al. 2025: 2), and communicating with others and improving self-esteem (Perez & Pepping 2024: 6). These reasons were not far from my own, and as I matured, I noticed that just as ‘my body began to adjust to my gender transition, so did the way that I viewed sex and my sexuality’, and so did my purpose for online dating (Bergdorf 2023: 43).

On the apps, I increasingly sought to use my body and transition to benefit myself, actively crafting an online world that echoed the possibilities of a self-determined gender transition. However, socially entrenched assumptions of a successful medical transition still followed me. On the platforms I used, many cis men seemed to assume that I would need to have had some form of ‘complete’ top and bottom surgery to be a trans woman. Such rigid narratives emphasise an extremely normative model of transness, premised on a conventional ‘chronology which affirms a finite beginning and end to transition’ (Lubinsky & Aultman 2024: 402). However, my own transitioning narrative is transgressive, alternative, and non-conformist. I use feminising hormones and have grown breasts and curves, but have had no top or bottom surgery. Nor do I use my penis during sex. I view my preferred expressions of embodiment as consistent with theories of trans-ing, which disrupt simplistic notions of transness as a linear before/after model by recognising the multiplicity of (trans)gendered bodily expressions that are often marginalised within transnormative narratives reliant on surgical transition and polarised binaries. By contrast, trans-ing is an ongoing and unending process that recognises how transgender identities are ‘capable of supporting rich and rapidly proliferating ecologies of embodied difference’ (Malatino 2019: 644). This radical transness has enabled me to shape my online dating experiences. It has also positioned me, in my own self-understanding, as an example of transnormative counter-narratives. Once I had come to understand my trans woman narrative as processual—a journey involving multiple steps, stops and starts, ruptures and erratic moments of progress, turns and re-turns—my purpose for online dating shifted from finding men to have sex with to finding ‘somebody who’s open and understanding and understands that love is more than the gender and genitalia that you have’ (Motter & Softas-Nall 2021: 63). Unsurprisingly, given the elusiveness of any version of ‘love’, this has been challenging.

Online dating profiles are constructed using a set of identity markers – name, age, gender identity, profession, relationship status, and a few photos. Mine read something like: ‘Elana, 30 years old, Trans woman, PhD candidate, Single’. These identity markers and the accompanying images are used to construct a specific narrative that aims to persuade cis (sometimes transamorous) men to match with me. (Transamory is a term used to describe men who are specifically attracted to transgender individuals.) A key point is that gender identity is central to the functioning of dating apps; it is a defining feature of how the apps are used by those who create profiles (MacLeod & McArthur 2019: 834). On apps such as Grindr, Bumble, Hinge, and Tinder, my trans identity has been perceived as an exception and a deterrent by some cisgender men because they did not expect a trans woman to be allowed on platforms that were previously understood as being only for cisgender individuals. Despite some prejudicial responses to my profiles, it could be argued that I hold a relatively privileged social position within the trans community, being an educated, attractive, cis-assumed (‘passing’) trans woman. These distinctions, informed as they are by society’s preferred, normative standards of class, appearance, and gender, potentially enhance the attractiveness of my online dating profiles. This is so even though, as Griffiths and Armstrong argue, dating apps ‘impose socio-cultural norms of gender onto app affordances, and thus affect how users interpret, acknowledge, and interact with gendered features on apps’ (2024: 120).

Let me briefly comment on passing in relation to dating apps and potential relationships. I recognised that my ability to pass could create tensions, provoking cis men who encounter me online to think they are ‘victims of deception and [entitled to] react with violence’ (Tomson 2016: 162). However, other cis men saw my passability as a potential benefit that could alleviate uncomfortable questions posed by society in relation to my gender identity and future relationship dynamics. Passing as cisgender does have its benefits, but it comes at the detriment of ‘embodying and enacting certain forms of femininity’ (Robinson 2023: 363). In my experience, trans–cis relationships are often dependent upon cis men’s preferences, where trans women who do not, or ‘cannot live up to dominant white middle-class expectations of what “looking like a woman” means, or who cannot access surgeries and hormones’, can be excluded or rejected (Robinson 2023: 363). Often, I would receive responses such as ‘you are very beautiful for a trans woman’, or that ‘nobody would be able to tell’, or that ‘I must have done something right’.

At the beginning of my transition, my need to pass ‘reinforce[d] the idea that [trans] individuals must adhere to certain physical traits […] to be sexually desirable’, or I would risk being rejected or not chosen on the apps (Griffiths & Armstrong 2024: 124). With time, and with the slowly growing inclusion of trans identities on dating apps and in society, as well as with my increasing engagement with transgender scholarship, I was presented with ‘opportunities for self-presentation and for interaction [that could counter] broad gender-based expectations and stereotypes’ (MacLeod and McArthur 2019: 828). Constructing my identity and presenting it in a self-imagined way, rather than simply taking on socially prescriptive ideas about transness, has enabled me to exercise agency. I can play into cis men’s desire, counter it, or combine versions of these approaches. On the apps, even while being very femininely presenting in my profile, I chose to counter many of cis men’s expectations, instead disrupting their narrow ideas about what it means to be a trans woman. The predominant assumption I encountered among cis men was that trans women are necessarily categorised as either ‘pre-’ or ‘post-op’. The recurrent belief on the apps was that a trans woman could always be expected to undergo sexual reassignment surgery, her body visibly in the ‘masculinised’ state of before surgery or ‘improved’ through the ‘feminised’ presentation of after surgery. Linked to this was the belief that there was a clear distinction between a supposedly incomplete and a complete transition. However, my interactions with cis men on dating apps challenged these normative models of transfemaleness. My image, experiences, and brief experiential accounts presented them with previously unknown and unconsidered alternative transgender narratives of becoming.

In this way, my transness, as I became more confident, also demanded that I become less secretive than in my early, ‘baby trans’ days. Despite passing, I never concealed my trans identity on dating apps. My profile explicitly declared that I was a trans woman, and my first question to cis men was whether they were aware of this. Disclosure was a key concern. Just as the well-known South African trans woman Anastacia Tomson explains in her memoir, Always Anastacia, ‘I decided it was in my best interest to declare my identity on my profile. There was little to lose’ (2016: 163). Being openly trans in all spheres of my life brought me peace and helped me to avoid the shame and indignity of hiding my identity. In the online dating world, too, being open was beneficial for managing reciprocal possibilities and boundaries. My explicit questions to my respondents acted as a filter and buffer to ‘avoid misassumptions, reductive understandings of [transgender] identities and overt hostility’ (Webster et al. 2025: 10). These questions also allowed me to filter out cis men who were not interested in me because I was trans. Further, such questions formed part of my own self-directed agency, positioning me not merely as a person reduced to (often) prying verbal examination, but as a woman composing her own online dating character and storyline. In effect, by being explicit about my transness, I performatively destabilised more conventionally sexualised norms of bodily explicitness, deliberately linking identity, intention, and self-definition to assumptions about normative gender embodiment.

Online dating for trans women comes with certain perceptions. As someone who is trans, you are expected to explain the various aspects of being transgender, to share personal and intimate details about yourself, your body, and your gender transition, to deal with people’s interrogation and questioning of your identity, and to mediate their personal reactions, beliefs, and sociocultural understandings of gender. This is an exceptional sociocultural burden when all you are hoping for is a sexual or romantic encounter, especially since cis men’s expectations primarily centre on trans women’s embodiment. Often, men ask deeply personal questions, such as what we have done to our bodies and what body parts we have. This intrusive questioning may stem from ignorance, prurience, or a practical wish to know what kinds of sexual engagement might follow. As I have discussed, some uninformed cis men believe that only if you are ‘fully’ transitioned can you be considered ‘a real woman’, while possessing a combination of male and female secondary sex traits renders you similarly incomplete and non-woman. Such binary assumptions derive from the socially dominant ‘trans medical model’, which has tended to popularise ‘being transgender [as] a fixed phenomenon that is only “real” if trans people have fully transitioned’ (Lampe 2024: 14). This normative model has become the established trajectory through which transness is viewed, evaluated, and interpreted by those outside trans communities and, sometimes, even by those who are trans. Malatino, by contrast, makes a point that has not yet been well translated into the world of dating apps, where trans women and cis men might meet. Malatino observes that privileging limiting transnormative narratives creates ‘damaging expectations for trans people who […] do not desire medical intervention’ (Malatino 2019: 638). Similarly, Bradford and Syed argue that transnormative assumptions aim to promote ‘respectable […] understandable images of transness’ because bodily and gender expressions that ‘deviate from these images’ may confuse cis men (2019: 318). I am not sure where that leaves me on dating apps, aside from my commitment to both passing and being out as a trans woman. Perhaps I can understand my seemingly incongruous stance as a political position, a minor but potentially significant form of agency. As I imagine it, trans women like me, positioned within the trans interregnum, ‘account for the creative and [self-]caring acts of trans intimacy that render life […] during transition, which may very well not have a definite end’, as liveable and understandable through active engagement that seeks to dismantle hegemonic assumptions (Malatino 2019: 635). On dating apps, I have consciously sought to bring together such critical rethinking with debates around transfemale experience and embodiment, refusing to be reduced by cis men to a clichéd body.

Due to their limited knowledge of trans bodies and lived trans experience, cis men interacting with trans women on dating apps often pose a series of questions to learn more about the person they are connecting with. The questions cis men asked me were both predictable and reductive: ‘What does it mean to be trans? When did you know you were trans? How did you transition? What is between your legs? How would we have sex?’ Most cis men wanted to know the same kinds of things, because they could not ‘tell’ from my profile pictures that I was trans. I looked like any other woman, rather than presenting as an ‘othered’ woman.

As intrusive as the questions were, the answers I gave presented me with the ‘possibility of experimenting with both [my] identity and [the] communication patterns’ typical of online dating apps (Masulla & Coppola 2021: 331). I replied simply. I said, ‘I changed my gender from male to female’. I never mentioned anything about sex or my body, preferring to avoid these complications. Unsurprisingly, this response proved inadequate for some cis men, who wanted detailed and intimate answers rather than what they perceived to be my withholding. If, or rather when, they asked how I had known about my transness, instead of the flatly predictable ‘I always knew that I was trans’, I would give a more nuanced reply that drew on my lived experience and my postgraduate studies. Possibly, this was too much for some men. Yet it was my story, and I needed to excerpt it my way. ‘My trans identity formed over time’, I would say. ‘All my life there were experiences, realisations, and indications of the incongruence between my preferred gender identity and my sex assigned at birth. With time, I knew’. ‘Incongruence’. Yes, I know. A big word to use in an online dating app, with a stranger and potential partner. But frankly, I leaned into my growing intellectual knowledge of trans identity construction and gender development. I enjoyed gently toying with the minds of some uncomprehending cis men, who habitually responded with an underwhelming, ‘Oh! That’s interesting’.

Some men showed a genuine interest in me and asked more complex questions. This allowed me to share glimpses of a trans woman’s life narrative that, as our chats revealed, they had never encountered before. Some cis men weren’t used to hearing that trans women didn’t necessarily have surgeries; that no single event always contributed to their decision to transition; and that they didn’t necessarily seek to penetrate men sexually, or that they had not inevitably been rejected by their families. My replies to cis men online disrupted the expected justifications for my transness. I refused to deploy the clichéd responses, even if these had been invoked by prominent trans women, to the extent that such ideas had become an entrenched transnormativity. Examples include: ‘I played with dolls as a child’ (Tomson 2016: 38), ‘I was born in the wrong body’ (Tomson 2016: 102), or ‘I always felt like a girl inside’. While these affirmations may hold true for some trans women, they did not directly coincide with my own trans experience, and in my online dating conversations I actively sought to complicate society’s narrow, taken-for-granted idea of ‘the trans woman’.

On the app, many cis men’s questions intrusively interrogated the physical characteristics of my body. I knew this intimate prying was not unusual online. Research by Webster et al. reports that trans people often feel ‘invaded in online settings, which involve being the target of unwelcomed interest and intrusive behaviour from others’ (2025: 11). Cis men’s questions also centred on my assumed medical transition, and not on its social and legal aspects. They did not seem interested in how I had begun socially transitioning: in 2014, when I left high school in Constantia and moved to Stellenbosch, a town historically shaped by apartheid, to start university; how I then experimented with and changed my clothes and pronouns. They were not interested in the legal aspects of my transition either. I have been living in my preferred gender identity since 2019, with my name and sex changed on all my official documents, from birth certificates to degrees. Such changes, which were crucial to me and an integral part of my transness, were insignificant to cis men. In the online dating space, where sex forms the constant implied horizon, their interest was piqued almost exclusively by my body and the changes understood to have been made to render it female. Many cis men fixated on my breasts, perplexed that I had breasts yet had not undergone surgery. This fascination is tied to the hypersexualisation of trans bodies and to how cis men’s sexual preferences and desires for certain body parts are prioritised. ‘But I see you have breasts?’ a man would say, at once questioning and exclaiming.

As I became accustomed to the invasive questions, I also became desensitised. No longer shocked, I began to reply archly: ‘Yes, I have breasts. They’re my own. I grew them myself.’ This response baffled some cis men, especially those who were unfamiliar with the effects of feminising hormones on the body. Most cis men assumed that transgender women required ‘top surgery’, or breast implants, as part of their transition. While such medical interventions are common in some parts of the world among more privileged trans women, they are not prescriptive. Predictably, the next question was usually about ‘bottom surgery’, or sex reassignment surgery. ‘Did you get surgery “down there”?’ they would ask euphemistically, if they were trying to be polite. More commonly, I encountered the bluntly reductive interrogation: ‘What’s between your legs?’ I instinctively recoiled every time I was asked this question. I always tried to avoid replying with explicit details about my genitals. ‘If you’re asking whether I have had “the surgery”, I have not. I definitely don’t have a vagina and don’t plan on getting one.’ Those cis men who were especially confused (or voyeuristic, or hoping to humiliate) often asked, without any decorum, whether I had ‘boobs and a dick’. I could hardly bear these crude, reductive interpretations of my story, diminished to mere genitals.

It is worth noting that many trans women I knew in Cape Town had not undergone sex reassignment surgery due to a lack of financial resources and the limited availability of public healthcare services. Such under-provisioning was fairly common knowledge in the dating scene and was reflected on dating apps, where cis participants often assumed that most local trans women were pre-operative and that a trans woman in Cape Town might be willing to use her penis during sex. This assumption caused me to feel ‘overwhelmed and fatigued by having to educate others’ through the repeated and continuous interrogation of my body and genitalia (Griffiths & Armstrong 2024: 124). Many cis men who were puzzled by my lack of surgery asked why I had chosen not to have it. I explained that this was my preference, that such surgery was costly, and that it came with major complications that could affect my health and quality of life. In my experience on dating apps, surgery- and genital-related questions often characterised the first line of inquiry by men who, as conversations unfolded, proved to be uncouth and demonstrated the least respect for my trans identity and my body. Still, I felt some degree of control. If my responses, however nuanced or challenging, were openly accepted by cis men, whether with the promise of an unconventional intimacy and/or genuine conversational engagement, the chat continued on my terms. If I was unhappy with the line of questioning, I ended the conversation.

As might be clear from the above, the relatively easier questions were those regarding my identity and becoming, whereas the worst questions were about sex. Tomson notes that ‘one of the tragic realities facing transgender people is that others seem to think that they have the right to intimate details about our bodies’ (Tomson 2016: 135). On dating apps, cis men, in particular, seem to feel that it is important to know such specifics in order to establish and confirm their sexual or romantic interest in a trans woman before continuing online conversations or going on in-person dates. Yet, as I am arguing, being on dating apps and speaking to cis men also gave me the opportunity to be transgressive, turning these interactions into a form of knowledge activism. My answers frequently defied men’s expectations, and both directly and indirectly I made it known that ‘there are many different ways in which a person can transition and that we do not all have the same end goals in mind’ (Ryklief 2021: 21). Scholarship suggests that cis men’s knowledge of trans bodies and transitioning is often drawn from their experiences of watching pornography (Webster et al. 2025: 10) and/or from exposure to transgender tropes that circulate in society. The question-and-answer exchanges on online dating sites enabled me to nudge my male conversationalists towards a far more nuanced and entangled understanding of a trans woman’s phenomenology, encouraging them to ‘understand personal, master, and alternative narrative construction within the [South African] social context’ (Bradford & Syed 2019: 309).

The effect of alternative or unexpected transgender narratives might have confused some cis men, and even dissuaded them from further engagement, but I viewed the dating site environment as a pedagogical space, a teaching apparatus for those who wanted to learn about themselves and others, not merely pursue sex. This possibility is also reflected in the scholarship. For example, Griffiths and Armstrong suggest that trans dating app users ‘wanted dating apps to educate others on transgender identities’ (2024: 123), thereby destabilising transnormative narratives of a complete transition that assume that everything has been changed about a trans person’s identity. This persistent misunderstanding of transness imposes cisgender expectations on trans people. The social assumption that there is only one, normative way to be ‘properly’ trans, supposedly evidenced by visible, surgical changes to embodied biology, reproduces binary ‘gender dynamics’ in the online dating environment (MacLeod & McArthur 2019: 828).

As I have indicated, in online dating apps, gender is constructed and mediated through the identity markers that are provided. These markers enable transgender users to obscure or share their gender identity with a degree of choice (MacLeod & McArthur 2019: 823). Dating profiles are the starting points of a user’s public-facing gender presentation and enable users to create and present alternative trans narratives to uninformed cisgender audiences. My own dating profile and the conversations I had with cis men emphasise that trans bodies are created in active collaboration with the environments and circumstances in which they find themselves and are not merely passive by-products of a life situation. As Lubinsky and Aultman note, ‘a body within trans becoming […] is one which is a phenomenological topography of affects […] re-energising bodily boundaries’, a body that develops via multiple, even conflicting, paths and values (2024: 403). There is no clear procedural timeline of a ‘before’ and an ‘after’, no simple authenticator of what is ‘real’ or ‘fake’. My conversations on dating apps revealed that cis men are not easily able to understand the complex ‘social manoeuvring’ of alternative trans narratives ‘in relation to transnormativity’, because such mobile and uncertain ‘positioning may have a significant effect on the perceived legitimacy’ of cis men’s own identities (Bradford & Syed 2019: 308). If gender binaries are fluid, if male and female are not polarities, and if ‘trans’ is an evolving and incongruous spectrum that might include multiple identity presentations rather than establish clear boundaries between an assumed self and a marginalised other, then a cis man’s preferred, relatively rigid identity may well feel threatened. Beyond threat, however, and imagined more positively, my use of online dating apps suggests that they offer an opportunity to hold conversations about the dynamic and unfixed nature of transgender narratives. Such difficult conversations could slowly prompt wider social understandings of transness, alongside a broadening of sexual and romantic possibility, while also serving to legitimise non-normative trans identities within the online dating space.

This is not a simple task. Even though transgender people and issues are gaining more visibility, ‘dating, sex and relationship formation can reveal ideas about prejudice and inequality and how societal attitudes shape intimate life’ (Robinson 2023: 357). An interesting angle emerges in relation to some of the positive reactions I have encountered among cis men. Sometimes this welcome in the online space has come from cis men who have had difficulty attracting or forming relationships with cisgender women. Such men claim that dating trans women is ‘a lot easier’ because they can relate to them (Robinson 2023: 367). Paradoxically, this claim is often rationalised by emphasising the past self of trans women, through the idea that ‘some things remain’ (Robinson 2023: 367). This need not refer to the penis, but rather to ostensibly ‘masculine’ cultural repertoires, such as relating to and understanding cis men’s humour, as well as what society designates as ‘male’ behaviour, hardships, and sexual needs. A trans woman’s imagined trace of maleness, in effect, is considered by these cis men to be a redeeming and attractive quality. Robinson also notes that some men see dating trans women as an opportunity to feel wanted and affirmed in their own rendition of masculinity (2023: 367). The positive reception associated with being attracted to trans women can influence cis men’s self-worth and shape how they navigate and express their own gender identity. Cis men with a greater understanding and pre-existing knowledge of trans issues have been shown to be more open and receptive to alternative trans experiences. This ‘queer relational form’, if ‘situated within a flexible or evolving understanding of heterosexuality’, could enable cis men to better understand their desire for and attraction to trans women (Hammack et al. 2018: 15).

Still, some cis men who were attracted to me were worried that their ‘heterosexuality [and] their masculinity [would] be called into question’ (Robinson 2023: 357). Due to the lack of information and adequate understanding of transamorous sexual desire, the sexuality of ‘gender-normative males’ becomes illegible to society (Hardy 2023: 130). Hardy explains that contemporary understandings of heterosexuality cannot accurately ‘capture the nuances of attraction, identity, lived experience and behaviour included in romantic and sexual relations’ because of the ‘binary position’ these understandings still assume (Hardy 2023: 25). Research has shown that ‘some cisgender app users viewed transgender individuals and their anatomy as an object for their own desire and often did not express interest in getting to know the trans individuals further’ (Griffiths & Armstrong 2024: 124). If cis men changed the way they framed their desire—from an attraction to trans women’s anatomy to an attraction to their gender identity—their heterosexuality would be far less likely to be questioned. By separating gender identity from sexual desire, cis men would be able to maintain their heterosexuality and masculinity while ‘adequately recognis[ing] trans women’s identification as women’ (Hardy 2023: 72).

It may be that pornography stands in the way of possible positive developments in cis men’s relations with trans women. I discovered through my interactions with cis men on dating apps that they ‘explored their fantasies around transgender people through pornography and then later projected these stereotyped ideas onto transgender individuals in person or on dating apps’ (Griffiths & Armstrong 2024: 124). Some men assumed that the pornography they consumed was a reflection of the sexual desires and appetites of trans women, but my immediate disapproval often resulted in a range of apologies and justifications from cis men. Hammack et al. also note that ‘these devaluing’ pornographic ‘discourses call into question the value of intimacy and relationships in sexual minority individuals’ lives’, and that their ‘negative impact is likely to be felt’ not only by trans women but also by cis women (2018: 7).

Since openly embarking on my transition, I have refused to play into the fantasies that cis men often project onto transgender women. Instead, I have insisted on my own sexual preferences, even when these countered and, perhaps, invalidated some men. Casually, I would respond, ‘I’m not looking for a man who sits at home and has depraved fantasies of a woman he hides from the public. The sex I’m looking for involves not just lust; there is tenderness and care. I’m not here to fulfil a temporary desire, but to actually find love.’ This often baffled them. I knew that ‘many of the [cis men] that fetishise transgender women see us as a kink, as something that they would only ever do in secrecy and behind closed doors’ (Webster et al. 2025: 10). My response brought their hidden feelings of shame to the surface, exposed the masks behind which they wished to conduct themselves online, and perhaps also in person. I was not interested in protecting their perverse online imaginaries. Playing into cis men’s fantasies places trans women at risk of sexual exploitation and devaluation, with damaging consequences for their health, self-esteem, and future sexual and romantic relationships.

Even though all trans–cis romantic relationships demonstrate the potential for validating trans identity (Monakali & Francis 2020: 15), this validation depends on the level of understanding and acceptance that trans partners possess in relation to trans identities. As a trans woman on a dating app, I only had control over the narratives I constructed and shared, and not over the reception and reactions of the cis men I spoke to. My own experience supports this claim. Cis men’s understanding of trans issues can be improved through exposure, personal reflection, and nurturing a developing interest. Many cis men are ‘naïve about transgender issues—the correct terminology, the matter of pronouns, the concept of dysphoria, [and] the process of transition’ (Tomson 2016: 173). But perhaps cis men can learn, in order to become a valuable ‘source of identity affirmation, particularly in response to microaffirmations from partners’, which refer ‘to relatively small gestures and behaviours that positively affirm a [trans] person’s identity’ (Perez & Pepping 2024: 2).

Examining my own online dating patterns has the capacity to expose the power imbalances within my experience of trans–cis relationships, specifically as they relate to Cape Town. Smithee explains that ‘romantic relationships of transgender individuals [with cisgender partners] may inherently be sensitive to […] differentials in power, based on societal differences in privilege’ (Smithee 2021: 3). Masullo and Coppola similarly argue that trans identities are placed ‘along the axis of power established by the gendered and heteronormative order crowned by cisgender, white, and heterosexual men’ (Masullo & Coppola 2021: 321). It is important to recognise the interrelation of physical and virtual topographies. In the material spatial geography of Cape Town, binary norms of gender ‘speak to the dominance of men’s power in who gets to navigate public spaces freely and safely’ (Monakali & Francis 2020: 17), and this dominance extends into online dating spaces, where cis men and their desires remain privileged despite the rules and regulations that structure the virtual locales of dating apps. Trans and cis becoming in Cape Town is still ‘undoubtedly shaped through settler colonial lenses, [where] geographical positioning is not the only power dynamic at play’ (Lubinsky & Aultman 2024: 406). Additionally, gender, race, culture, and socio-economic position all shape the power gap between trans and cis dating app users. My own identity markers—being trans, a woman, Coloured, heterosexual, from an underprivileged background, and living on the Cape Flats—place me on the lowest level of the axis of power described by Masullo and Coppola. The Cape Flats, constructed through the apartheid government’s sweeping racial segregation and forced removals of Coloured and Black communities from the prosperous ‘white’ city, clustered so-called non-white populations on the urban periphery, in crowded environments that remain underdeveloped, under-serviced, and marked by a lack of resources. Consequently, living on the Cape Flats made dating difficult. I was unable to access more suitable, urbane cis men who lived in the city centre and were open to dating trans women; nor could I ‘host’ or accommodate anyone at my family home. And I did not own a car. In summary, the men I matched with on dating apps were cisgender, hetero/bi/pan/demi-sexual, and from diverse racial, socio-economic, cultural, and geographical backgrounds within Cape Town. Yet it is their cisgender identity, and their relative proximity to whiteness, wealth, and the city centre, that place them in positions of greater privilege than mine. And as much as I desired access to a suave urbanity, this imbalance of power and place situated me at the mercy of cis men’s desires and preferences, compelling me to align myself with the very axis of power in order to be chosen.

In conversation with a friend, I was reminded that this power imbalance was what guided my sexual experiences and relationships with cis men. There was a time when I spoke to multiple cis men on multiple dating sites, navigating a space where sex and my body became a currency that I could exchange for simple, ephemeral pleasures—a night out, dinner, drinks, drugs, and sexual pleasure. In December 2019, early in my transition, I experienced the most attention from cis men. This was the tourist season, when Cape Town hosted international travellers and visitors from other provinces. I was under the impression that international men were more open-minded, understanding, and aware of what it means to be trans. I assumed that they were more willing to engage with me sexually than South African men. The conservative attitudes that have shaped South African masculinities—among them traditional culture, religion, and rigid gender binaries—had, in my experience, made local cis men in Cape Town afraid of exploring their desire for, and attraction to, trans women. Perhaps they feared that the shame, rejection, and discrimination faced by trans women might be transferred to them. But, as Janet Mock argues, ‘as long as trans women are seen as less desirable, illegitimate, and devalued women, men will continue to frame their attraction to us as secret, shameful, and stigmatised, limiting their sexual interactions with trans women to pornography and prostitution’ (Mock 2014: 207).

International cis men were in Cape Town for a short time. Their temporary stay placed significant limitations on establishing a romantic relationship, and our encounters would therefore be based entirely on the prospect of having sex together. Every conversation I had followed the same pattern: inquiring what they were on the dating app for; whether they were interested in hooking up; where this would take place; how I would be getting there and back; and what the sexual limitations were. In every conversation, I made it known that I was uncomfortable with sharing my ‘lady bits’, ‘my original plumbing’, my penis. Still, most of the cis men who were attracted to me centred their attraction around my genitals. This made me feel extremely uncomfortable. When I was asked ‘Why?’, I explained that I felt no pleasure from engaging with my penis sexually and that any attempt to do so would certainly ruin the moment. Griffiths and Armstrong observe that, for trans people, expressing boundaries ‘about touching specific body parts or what terms to use’ helps reduce ‘gender dysphoria during sexual encounters’, but in my case, constantly talking about my genitals amplified my discomfort online (2024: 125).

In essence, my conversations with international cis men were negotiations of access to my body and the sexual acts I was willing to perform. While research suggests that trans women ‘found online settings helpful in providing a physical barrier when navigating potentially uncomfortable conversations such as negotiations about sexual practices’ (Webster et al. 2025: 12), this was not unproblematically the case for me. The discomfort I experienced through this online parleying seemed to affect me physically, since my trans identity and the composition of my body necessitated complex, mediated ‘negotiations of sexual dispositions (such as bottom, top, versatile) and activities (such as kinks or behaviours)’ as if these were essential aspects of ‘getting to know others and assess[ing] compatibility before a new sexual encounter’ (Griffiths & Armstrong 2024: 12). Paradoxically, however, these difficult virtual discussions of boundaries and limitations to material, in-person sex not only caused discomfort but also increased my sense of control, as I deliberately steered sexual encounters away from kinks, fetishes, or the kinds of practices that tend to characterise trans–cis pornography. I preferred to keep things ‘vanilla’: specifying preferred sexual positions, avoiding excessive foreplay, and focusing on the cis man’s orgasms. While these discussions were uncomfortable, this explicit boundary-setting also protected me and saved me the anguish of dealing later with face-to-face emotional distress related to my body and trans identity. Nevertheless, these encounters were marked by emotional ambivalence. After sex, I felt a sense of ease in knowing that I would never see most of them again. At the same time, I also felt a degree of sadness in leaving their company, as they were often the men who had treated me most like a woman, shown me pleasure, and respected every limit and boundary I had placed on them.

As time progressed, my relationship with cis men, my body, and intimacy shifted further. My emotional, sexual, and intellectual expectations changed. I no longer negotiated, but asserted my own expectations, values, and boundaries. My transition demanded that I change not only my body but also the way I conducted myself and managed other people’s expectations of me. In my experience, cis men have often maintained their masculinity ‘through reinscribing gender-essentialist ideas about the gender binary and through constructing trans women as […] hyper-submissive’ (Robinson 2023: 362). I subverted and countered this construction, advocating my own narrative of being a powerful, independent, and pioneering woman who both bolsters and complements my partners’ masculinity. Monakali and Francis, in their work on trans masculinities, note that gendered constructions are ‘not the exclusive embodiment of bodies assigned to the [gendered] sex, but a collection of roles, behaviours, and imaginaries that are continually being challenged and, as such, transform’ (2020: 4). Transgressing traditional gendered constructions has enabled me to reimagine and actively experiment with the limits and possibilities of my ever-changing trans intimacy and trans narrative.

I matched with my ex-partner on a dating site called Hinge. Hinge aims to help people make genuine relationship connections via an award-winning algorithm designed to give credibility to the truism ‘find your perfect match’. In our early online conversations, I jokingly told my ex-partner that my previous dating experience demanded that I request a curriculum vitae, a police clearance, a medical report, a three-month bank statement, and three references before I considered being in a relationship. He got the joke, and yet understood the seriousness behind it. He seemed familiar with the issues that trans women encounter on dating apps and, although he had grown up in South Africa, he was not a citizen. From his side, while getting to know one another, he shared his complicated and intimate history with sex, prostitution, drug use, and domestic violence. This was all a red flag to me, initially making me uneasy. Because of his past, he had never been in a healthy, loving, and respectful relationship before.

Here, the trans–cis elements of our developing intimacy were placed in a far more complex relation than either of us had anticipated. The initially distinctive elements of our conversations—his cis identity and my trans identity—became dialogically and intersectionally entangled with many other dimensions of our lived experience.

On dating apps, there is only so much you can learn about another person, and throughout our relationship, the imbalance in our emotional and intellectual capacities has illustrated the realities of our respective dispositions. From the start, online, he was an independent, privileged, and financially stable cis man with addiction issues, narcissistic tendencies, and unresolved trauma. Despite my frank critiques of all three, a dependency on me developed. I began to take on the roles of personal psychologist, spiritual guide, parent, teacher, and girlfriend. The situation was moving far beyond the virtual confines of the dating app, and even beyond the functional parameters of hooking up and sex. We were becoming closer; the app having served as a generative gateway to the discovery of the self in relation to an other. In my view, the limited information users receive from dating profiles, and the brevity of early conversations, are insufficient for assessing compatibility. The primary goal of these apps is not to enable deep mutual understanding, but to facilitate expedient sexual connection. After getting to know him, however, I found myself awkwardly undertaking the feminised gender role that his own fragile masculinity needed to project onto me. Upon critical reflection, I came to understand what was unfolding. Hammack et al. note that the ‘gender labour [trans] women do in their relationships with [cis] men to validate and celebrate their partners’ masculinity […] suppress[es] the complexity of their own gender and sexual subjectivity in service of this goal’ (2018: 10). I also understood that cis men who feel pressure to embody rigid masculine gender roles ‘can experience negative health effects’, including high ‘levels of stress, depression and anger [that] may have a negative effect on relationship health with trans women’ (Celemen et al. 2024: 12). For his sake, and for mine, I wanted to mediate this stress by encouraging him to become ‘more aware of how [he] engaged in stereotypical behaviours and [how he could] work to increase the egalitarianism in [our] relationship’ (Motter & Softas-Nall 2021: 64). Despite his own experiences and past relationships, he was not fully aware that ‘no gender is or can ever be perfectly performed, embodied, [or] lived’; nevertheless, he continued to strive towards masculinity in our relationship, something evident in his behaviour during our dates and in the conversations we had outside dating apps (Lubinsky & Aultman 2024: 402). In this sense, the virtual world of dating apps percolated into and extended offline in potentially generative ways. My experience suggests that seeking, online, to negotiate a heightened awareness of masculinities and femininities as relational constituents of intimacy can be a significant element in the development and deepening of an ongoing, in-person, trans–cis partnership.

Well-known dating apps such as Hinge, Bumble, and Tinder have broadened their policies to include trans identities and have recognised the role they play in combating social bias, prejudice, and stigma that the trans community faces (Perez and Pepping 2024). But some accountability also lies with cis men to respect and uphold the dignity and integrity of trans women on dating apps. In terms of a trans woman’s responsibility, disclosure on dating apps seems essential to establish ‘certainty and safety’, and proactively doing so is an ‘effective strategy […] to avoid the many repetitive communications’ on the subject (Fernandez & Birnholtz 2019: 18). In response to the fetishisation and objectification of transness, a trans woman’s deliberate mediation of the conversations that occur between her and cis men on dating apps has the potential to assist cis men in developing a deeper understanding of trans women. Here, ‘understanding’ becomes an open, processual space, a ‘safer space [than society tends to allow] for’ trans women. Through the question-and-answer process of difficult conversation, the simplistic and damaging transnormative ‘knowledge project’ is suspended ‘in favour of the activity of […] understanding, which is inherently uncertain precisely because it is tentative, interpretative, and provisional’ (Smith 2024: 7). Studies on trans dating and trans intimacies suggest the need to reflect the growing ‘complexity and diversity of human intimacies’ beyond cis society’s binaries, especially by focusing on how the trans–cis relationship model is ‘orientated towards (…) normative ideals’ while simultaneously ‘defying received notions of heterosexuality’ (Hammack et al. 2018: 14). As the present paper suggests, the profiles and conversations that characterise online dating apps have an important place in mediating this change. My own online experiences of trans–cis dating have led me to conclude that if cis men were not overtly ‘fixated on sexual pleasure’, they would be able ‘to fulfil their gender and sexual roles’ in more satisfying ways (Hardy 2023: 123).

In chatting on these platforms, and in writing this paper, I have aimed to give voice to my experience as a trans woman while pushing back against dominant, normative (mis)understandings of trans lives, becoming, and intimacies. In disrupting received ideas, I have also emphasised the need for cis men to risk talking about their desires in non-fetishistic language. Robinson notes that we ‘need new ways of relating and desiring one another that do not rely on the production of gender difference and the erotic attachment to gender inequality’ (2023: 371). My encounters and conversations on these apps were marked by volatile degrees of curiosity and close-mindedness, by hospitality and hostility, by tentative reception, and crude rejection. Perhaps this is how change in trans–cis relations can occur: through fragile and elusive slow intimacies that are based on a ‘deep reading’ of different lives ‘that is transformative’ because it is attentive to ‘what it regards’ (Ellis 2024: 7).

Acknowledgement

Sally Ann Murray (Prof.), Department of English, Stellenbosch University. Thank you for helping me shape this article conceptually and expressively; without your extensive input, I would not have been able to publish my first publication.