As a trans woman in London, I’ve found myself going on quite a few first dates. Luckily for me, I adore a first date—the anticipation, the nerves, the thrill of learning new things about new people. Even if the date isn’t perfect, it’s still an opportunity to connect, to discover something new about someone else and, often, a little about myself. That’s something I’ve always relished.

A Cheeky London Lad

This is the story of a particularly memorable first date from many years ago, with a guy called Chris. He was a setup from a wonderful friend who knew my story and was confident we’d hit it off. Chris was a finance guy by day (clearly with a love of T-girls by night!)—handsome, a little older, and carrying just the right amount of cheeky London charm to intrigue me.

We had been chatting by text for weeks. Yes, this was 2006—the era when texting was everything. Our exchanges became increasingly flirty and cheeky, and I ADORE a cheeky London lad. Chris seemed to fit this bill perfectly. Now, the time had come for that delectable first meeting.

Butterflies and Building Confidence

At this point, I hadn’t been in the City long—just about a year. It was enough time to start unveiling the feminine side of myself to the world, but not quite long enough to perfect it (I’m still working on that part, lol). I lived in a shared house in Canada Water, just south of the river from Canary Wharf. Our riverside location boasted one of the most stunning views in the city, and my housemates—a German girl, an English guy, and another English girl—were some of the few people with whom I openly shared both sides of myself.

They were amazing. They helped me with makeup and styling tips as I was still finding my footing. On the day of my date, I had my nails done, showered, and was just finishing up. (My ritual hadn’t quite taken shape yet, if you want to know about it click HERE — shared house living makes some things tricky.) Then came the text from Chris: “I can’t wait to see you.” My stomach did a flip.

Butterflies. Delicious, nerve-wracking butterflies. My confidence was still blossoming, and the thought of being out in public was exhilarating yet terrifying. But those butterflies… oh, I love that feeling even now.

Chris must have sensed my nerves because he picked the perfect location for our first meeting: a drink and bite to eat in Canary Wharf. At the time, it was still developing and wonderfully quiet on weekends—ideal for a shy, newly emerging girl like me.

Disaster Strikes!

Canary Wharf has always held a special charm for me. The clean lines, brand-new buildings, and sense of sleekness are mesmerizing. Even now, though it’s bustling with activity, I love how people there are so preoccupied with their own lives that they barely notice what’s happening around them. It’s blissfully anonymous—a perfect place for me to feel comfortable.

Chris had chosen Gaucho Grill by the riverside, a spot I highly recommend for its stunning views. Wanting to make the experience extra special, I decided to treat myself to a boat ride across the river. The little river taxi shuttles between Canada Water and Canary Wharf all day, and as I set off, heels clicking delightfully against the pavement, a warm breeze caressed my smooth, stocking-clad legs.

But before I could even step onto the boat, disaster struck.

Right in front of the ramp stood one of the receptionists from my work. I swear, in that moment, every second seemed like a day. What should I do? I couldn’t turn and run (hadn’t learned to run in heels yet), but I also couldn’t stop—what if they clocked me?

In the end, I had a “fuck it” moment and pushed forward. I’ve always known I’m nearly unrecognizable in my two different guises, but this was the first real test.

She nodded an appreciative nod in my direction as I got on—and that was it. I had gotten away with it!

My heart was racing, and I could feel my face flushing beneath my makeup. “Fuck, fuck, fuck, fuck,” was all I could think as I hurried to the front of the boat and sat facing the opposite direction, just in case. The lapping of the water against the hull of the boat, mixed with the gentle rocking, eventually lulled me back into a state of nervousness rather than outright terror.

A Gentleman’s Charm

As I sat, I mentally checked myself again: Was I matching? Check. Did my little black dress show just enough without showing too much? Check. Did I have an opening line ready? Check.

We were all set. 🙂

The boat pulled in, and off I tottered (heels clicking). I had made sure Chris was already there and made my way into the restaurant, always a nervous moment.

Then it happened…

He stood up and stretched out his hand. I instinctively went to shake it (old habits die hard) and was shocked when he took it and kissed it—proper old-school gentleman style.

Suddenly, I was lost—my lines gone from my head, speechless and only able to laugh nervously. When I finally caught myself, all I could say was, “Well, that was a first!”

Quite possibly the best icebreaker of any date I’ve ever had. Chris still sticks in my mind because of it.

A Lovely Memory

We had a wonderful evening and another few great dates afterwards until, as happens all too often, we drifted apart and decided to remain friends. We’ve stayed in touch, though we don’t speak much anymore.

The Moral of the Story:

So boys—the moral of the story? If you’re thoughtful and gentlemanly, you’ll get a long, long way with a girl like me. 🙂

“When a girl finds her freedom in London, she discovers a life worth living. For in this city, there’s no end to the beauty, adventure, and joy waiting to be embraced.”

This is my take on the quote from Samuel Johnson…

“When a man is tired of London, he is tired of life.”

I feel like it fits my story.

You may know that my voyage to true self discovery was kickstarted in Belfast but only really began to take shape when I arrived in this beautiful city in late June, 2005.

I still remember it vividly, the excitement of being in a new city. The fear of not knowing what was ahead. The pure wonder of the cultural differences between London and Belfast.

I lived just south of the river at first, initially in Bermondsey – the wonderful Dickens estate, right next to Shad Thames and Tower bridge which are both stunningly beautiful, if the estate itself isn’t necessarily the most beautiful!

My first port of call was to get myself some kind of job, I figured Sports Massage would be a good shout so enrolled on a course in Finsbury park, starting first week in July, I marvelled at the tube and how easy it was to get everywhere (I still have to remind myself of this in my now, normalised form).

However, on the first Thursday of the course, the day after London had been granted the Olympic games (and we all had a massive party in Trafalgar Square) I arrived to Finsbury park to a very somber (and sparsely populated) room. In the time it had taken me to grab a coffee and some breakfast a bomb had been detonated on the tube at Kings Cross station on the Picadilly line – it was one of three tube bombs and one bus bomb that were detonated by terrorists that day and changed the landscape forever.

Looking back I figured out I must have missed it by two trains (which I am sure lots of people also did), I remember being acutely aware in that moment of just how fragile life could be – and thinking it would have been ironic to grow up in Northern Ireland then get taken out by a bomb in London a week after moving.

Anyway, I tell this story not to be depressing or to defile the memory of those that lost their lives, but because it loosely led to my first ever experience with another boy (not on that day obviously).

There were only a few of us who got to the course that day, and we were all promptly stuck there!

Fortunately, one of our classmates was a black cabbie (I LOVE black cabbies, probably another story in there for later). So he generously offered to drop ALL of us home – which at the outset was nine of us!

One in the front, 8 in the back, with only five seats meant that 3 of us were on the floor, oh what a squeeze it was! Anyway, the three were me, an absolutely stunning blonde girl who lived very close to me and who ended up becoming a great friend and HIM.

He was from the world largest continent, in the southernmost part lets say (don’t want to be too specific), handsome with dark hair and defined features and was a professional ballet dancer who was coming to the end of his career – lets call him Tony.

We were sat next to each other on the floor and I could just feel ‘something’, we got on well (for the short time we had been on the course) but in this moment, squeezed together amongst bags and feet in the back of a cab there was something else there.

I will write a post about our ‘encounter’ in a week or two, I feel he deserves credit for gently and softly introducing me to the joys of mans body could bring to me!

But outside of this tragedy, and the subsequent tension arising, I was finding my place.

That place was Soho!

I know, I know, it’s a cliche, LGBT person loves soho, shocker – but you will come to realise that really I am just one big cliche, and I am never not going to be proud of that!

Soho was the place where I first saw two guys holding hands, where I realised that everyone was so friendly in a pub was because it was a gay pub (lol) and where I saw my first, real live, trans-woman.

My love affair with Soho is almost as strong as my love affair with my heels (almost) – although it has changed so much in the last 20 years (thankfully the human trafficking supporting brothels etc have all gone), but the essence of the place is still there.

If I am nearby I will ALWAYS pop into the Ann Summers store on Wardour Street to get myself something sexy to hide under my clothes (pro tip, lingerie is the best invention ever, but only if you understand it is for YOU, prying eyes should only be allowed to see it if they have earned the right – well, in real life anyway). I’ll usually pop into the ‘toy shop’ round the corner to get myself a little treat as well but that is for the subscribers section 😉

Anyway, back to the trans-woman.

I was in awe, the confidence, the grace, the poise, she had everything I wanted for myself. I plucked up the courage to talk to her and was astounded by just how sweet and lovely she was.

On explaining my own situation she took time that she really didn’t need to, to talk to me, sensitively and give me guidance on how best to take the first steps.

I will always be eternally grateful for this conversation, although our encounter was left there, as a beautiful and sweet side note to the story but nothing more, I am certain I would not have had the amazing experiences I have had if it didn’t occur.