Tamzin discusses dating, the sexualisation of trans women's bodies, and the importance of just living with writer, podcaster, activist, and model Alex Woolhouse.

Content warning: This article explores themes related to transphobia and suicide. 

When I meet Alex on Zoom she’s wearing pink hair rollers and preparing for a date. I’m hoping to get the low-down later in her podcast, “How Not To Get A Boyfriend”, where she exposes the dating scene of South London through the lens of a straight trans woman using hilarious, endearing, and relatable anecdotes. Alex describes herself as “Clapham’s Carrie Bradshaw”, and as a fellow South London girl I totally get it: she is confident, charismatic, and as brash and bold about love and sex as Carrie is. Unlike Carrie, however, this confidence in her identity wasn’t always evident.

Growing up in Wakefield, she navigated her all-boys school as gay, explaining that it was the “easiest frame of reference at the time—seeing that gay men could be femme”. It wasn’t until university in Durham that she began properly examining her gender. “In my first year, I started spiralling. . . I was like, I don't think I'm a man”, she says, before recalling some moments that allowed her to explore her femininity more deeply. Full disclosure here: I was also at Durham, a couple of years below Alex, and clearly remember one of those moments. She came down the catwalk at our university fashion show in an incredible blonde wig and a stunning dress and the whole room felt the whoosh of energy she brought. “Those kind of experiences at university were touchstones for me in realising that I was a girl,” Alex recalls. “I felt my most powerful, like I wasn’t acting”. It was a point of no return.

Having understood her gender identity Alex’s next step was to undergo a gender affirming medical transition. Whilst not the route for everyone, for her it meant “First getting a diagnosis of gender dysphoria, then being referred for hormone therapy, . . . and getting facial feminisation surgeries—all through a private doctor”. She’s also in the process of getting gender confirmation surgery, also privately, a choice she was able to make because she was working in a high-paying law firm and has supportive parents—but that’s not possible for some people. If she had gone through the National Health Service, she might still be waiting. A 2018 study found 27% of trans people in the United Kingdom (UK) wait at least a year for just a first appointment, whereas Alex is now four years into her medical transition.

It’s a position of privilege Alex fully acknowledges but firmly believes shouldn’t exist: 

“Unfortunately, we're in a situation where it's still a very specialised and little understood medical area. While being trans isn’t a physical ailment in itself, gender dysphoria can feel very much like one. For me when my body doesn't align with my womanhood and femininity, it feels like I'm going to be sick.” For her, this feeling is only alleviated by looking and dressing the way that she wants to and accessing that vital care—care (including healthcare unrelated to their transition) that 41% of trans people in the UK said was lacking because staff lacked proper understanding of their needs.

This lack of understanding is reflective of mainstream representations of trans lives and identities, which still remain limited, and often ignorant, to the nuances of trans experiences. Alex describes how these popular depictions of trans femininity shaped her own self-identity before she transitioned: she admits being “slightly embarrassed by the person I was at university. I was so keen to lean into a stereotypical, bitchy, gay, femme presentation.” Expanding her definition of femininity went hand in hand with understanding her own trans identity and has made her a kinder and more open person. I can see how Alex felt this way; the mainstream media representation of femininity for anyone assigned male at birth is frequently depicted as a performing drag queen ‘throwing shade’ or as the sassy gay best friend.

We talk some more about how trans narratives are so often confined to the transition process, ignoring the complexities and richness of life seen in stories cis people are allowed to tell about themselves. Trans people in stories are often reduced to offensive, one-dimensional characters. Research by GLAAD¹ found that in the four years since 2017 there were no transgender roles in the top 400 major studio films released, with the last non-binary character found being a disrespectful caricature in 2016’s Zoolander 2—a stark misrepresentation of the estimated 1% of the UK population that identify as trans or non-binary.

Alex’s podcast, How Not To Get A Boyfriend, adds to a growing pool of trans narratives in the media. She explains how, while it’s important to have people specifically fighting for trans rights, her calling is to address the lack of trans stories in which they just live: “I want to see more about trans people's lives and what it's like to date and live doing ‘whatever’ as a trans person . . . I sometimes talk about being trans but it's not a podcast about being trans . . . it’s a podcast about dating first and foremost”. 

In terms of normalising trans relationships she has her work cut out. One media form that has boomed in the last year with trans representation is porn: in 2022, Pornhub’s videos labelled “transgender” increased in popularity by 75%, becoming the third most popular category in the United States. While some might assume this is a step in the right direction of acceptance, Alex is firm about the damage done from only encountering trans bodies through the lens of porn: “It’s depressingly normal in porn for trans female bodies to be positioned as sexually taboo and salacious, and so as soon as I say I'm a trans woman, that’s often [cis men’s] only frame of reference. So, within a straight male culture, the only way that trans women are accepted is via sleeping with them . . . I hope that on my dates I’ve shown I'm a person who is worthy of respect regardless of whether they want to sleep with me. Also, trans women of colour or trans working class women will have a completely different set of concerns, most likely involving personal safety. And of course, these are challenges all women face”.

Another dating difficulty Alex describes is the coming out process. “I no longer subscribe to having to tell a guy before a date—it's information that puts me in a vulnerable position when dating and so I only share it if I trust him to still treat me as a human. That's the baseline. I don’t owe him that information until he shows me that.”

I ask Alex what made her decide to be publicly out in the media, given the difficulties it can present in her personal life. She replies, “There was a point where I was asked to do Channel Four's A Guide to Dating, which was about trans perspectives on dating. I had to sign a waiver saying this could be watched by millions of people and will be available online for the rest of your life. I worried about that. It wasn't because I am ashamed of being trans—quite the contrary—but it's something that I want to be in control of because I know others can see trans as something shameful or wrong. I thought hard about dating at the time because I was worried that I wouldn't ever find someone who would be happy being with a publicly out trans woman. But then I had a lightbulb moment of, ‘I don't want to be with anyone who isn't cool with me being trans and who is bothered by what body parts I was born with’.”

Alex clearly feels it’s important to share her experience, “I don’t have the time or luxury to wait for it to become normal to have a trans girlfriend, so I have to make it normal and I'm going to do that by talking about my experiences in my podcast and elsewhere. People will see that it's exactly the same as having any other type of girlfriend, just with a few more interesting things”. Alex has explored the challenges trans people face in dating, but these are not the only relationships that matter: family and community also count for a lot.

Alex is grateful for her supportive and loving family, but not all trans people have that luxury. For this reason, the concept of ‘chosen family’ is well known within the LGTBQIA+²  community. According to Stonewall, one in seven trans people in the UK hide their gender identity from their families. Alongside rejection can come homelessness, depression, anxiety. Alarmingly, almost half of trans people have considered suicide. While enjoying her own family’s support, Alex also values being connected to other LGTBQIA+ people, recalling an event she attended for Transgender Awareness Week: “It was a room full of trans people and we were laughing so much because we could relax and joke about stuff that we couldn’t in front of cis people”. That’s not to say that she doesn’t value her cis friends; she speaks lovingly about her friendship with her neighbours who are a gay couple, saying, “they’re men, they’re cis, they’re not going to understand everything I go through as a trans person. But we’re all coming from a similar place, want to understand each other, and are enjoying educating and talking to each other.”

I asked what advice Alex would give to younger trans people or those coming to terms with their identity on how to navigate love and relationships in a healthy way. She’s clear that constant questioning is vital. “So much of LGBT dating when you're young is online. There are ways to make sure you’re talking to people your own age and aren't being exploited, because it's so easy for trans people to look for external validation of their transness in romantic relationships. Be very aware of that and the reasons that you might be settling for less. Question them because, while they should make you feel good in the moment, they should also help you grow into a person that can be in a healthy relationship and can recognise love and adoration.

Alex explains there’s a lesson for everyone here: “Don't look for validation from others because the only person who can validate you is yourself. I have to tell myself this all the time . . . there’s stuff that I accept in relationships that none of my cis girlfriends would think acceptable. It’s hard to be rejected [as a trans person]; not only to be rejected for yourself as a person, which everyone has when dating, but to also be rejected for your transness or your trans body, something that you also might detest about yourself. It’s really hard to bounce back from that”. Put simply, she says, “Dating, and sex should be fun. Don't do it if you're not having fun.” 

And Alex does seem to be having fun. She’s on the verge of adding ‘novelist’ to her list of achievements, writing a fictionalised memoir on sex and relationships and how they’ve changed her throughout different stages of her transition. “Think Fleabag, Sex in the City, Bridget Jones . . . I’m just trying to be a trans Dolly Alderton. I don't know when it’s being published, but I'm signed with Watson Little. Hopefully it'll be available soon.” And with that I leave Alex to finish getting ready for her date, certain that she’ll continue having fun while learning more lessons in love and life to share with all of us. As she says in her podcast’s intro, “We’re all in the trenches together”.

You can find Alex on her Instagram @Alexwoolly, or on her podcast, How Not To Get A Boyfriend.

¹ Gay & Lesbian Alliance Against Defamation

² LGBTQIA+ includes people of all genders and sexualities, such as lesbian, gay, bisexual, transgender, questioning, queer, intersex, asexual, pansexual, and allies.