feature image photo by Samantha Brooks
Picture it: You’re a trans guy and you’ve met a stunning, charming, brilliant trans girl.
Maybe you were at a tech conference in San Francisco, or at Ultra, the annual electronic music festival in Miami. Maybe you went to a burlesque show at a downtown club. Maybe Blue Velvet was playing at a local independent theater and you locked eyes across the soda stand. Maybe you were set up by friends or matched on an app.
Either way, you’ve lucked out, brother. T4T relationships can be really affirming and fun. Dating someone who understands your transition can be wonderful. Fucking someone who has also thought about their body in an unconventional way can be enlightening and hella hot.
But my goodness, trans men, how do you speak to and then eventually woo the trans woman of your dreams?
I’m here to help.
How to Start the Conversation
This works if you’re in public and she’s a stranger or if she’s someone you’ve seen around and you wanna take it to a flirty place. Hell, it could even work in the case of a DM slide: Compliment. Her. Outfit.
We trans guys have an advantage over basic cis men here. We know what goes into a woman getting dressed up. There’s steps! There’s try-ons and discards, lotions and perfumes, accessory choices, sometimes shaving and plucking, and all sorts of to-dos specific to someone who’s thought out their gender presentation.
While women lament men who call them “natural beauties” when they’ve clearly had Botox and are wearing makeup, we’d never make such a mistake. The work of leaving the house as a trans person deserves recognition — even if that work is just how she styled her Fiona Apple graphic tee or her choice of running sneakers. Compliment her with more specificity than a cis man could ever muster.
What’s the brand of her adorable thigh-highs? Is she wearing her “season” as told to her by a TikTok color analyst? Did you once have a heart shaped choker just like that when you were a woman? Start there.
Only compliment her on what she can control or what is mostly non-sexual. No great tits, even if they are great tits. (You can compliment those later.) For now, we go to “beautiful eyes” or “nice hair” or “cute clothes” and then we add a specific.
Examples:
“Your shirt matches your eyes perfectly! You must have done that on purpose.” (Most people with nice eyes have absolutely done that on purpose, but they’ll delightfully pretend not to have.)
“I never got the hang of French braids when I was a girl, but yours are perfect. Did you do them?” (This has the added bonus of casually letting her know you’re trans too.)
“Your shirt is so cool. Is it a reference to something? Oh, a DnD podcast? Which one? I always wished I’d gotten into that but I’d have no idea where to start.”
How To Get Her Number
Now, how do we move from chatting to getting her information for a date? First of all, make sure she knows you are asking for romantic reasons!
Sometimes with trans people, we’re so worried about being vulnerable or so unused to being hit on in a serious way, we might not communicate date intentions well or understand we’re being asked out. And since you’ve hopefully dropped into the conversation that you’re also trans, she won’t have the anxiety of wondering if she has to out herself to you and risk negative results.
Say, “I’d like to take you out on a date sometime.” Relate it to something you all have been talking about. For example, let’s watch that old foreign-language lesbian film you’ve been recommending. Or, if conversation hasn’t lent itself to a natural hang suggestion segue, invite her to a trans thing. You and her already have something huge in common. It’s another advantage we have over cis men. (More on where to take her in a second.)
If getting her number seems too intense, or if your phone still shows your deadname when you call, it’s perfectly acceptable to ask for her Instagram. The dolls tend to curate their Instagrams really beautifully. Let her show it off!
Now that you follow her, you have to actually message her with a plan. Do not chicken out! Cis men have no spines, but we are not cis men!
Look, you had to tell people you were a whole other gender. You can message a hot girl on the ‘gram.
Where To Go On Your Date
It might be okay to lean into some ideas that are cheesy and gendered, like bringing her flowers. For some girlies, that will be too intense. But for others it might be totally cute, because a lot of us never had those formative experiences.
When in doubt, roses are way too much but anything else the grocery store has to offer is just right. I’d make sure it’s something hypoallergenic, not too fragrant, and not poisonous to pets. If flowers seems like it’ll freak her out, or it’s not your speed, you don’t have to do it! But feel it out. Maybe your version of flowers is pulling out her chair for her or buying the first drink.
Speaking of, you can do the regular coffee or drinks date — always keeping coffee as a low-pressure option in case she is sober. You can also just take a walk around a lake or generally window shop if you’re low on cash. But if you wanna be more specific, like I hinted at above, there’s luckily an existing trans connection!
Maybe there’s an independent queer bookstore or a trans drag show or an anarchist lecture series at the LGBT Center. I know this might not be the case for every city, but look on Instagram or Tiktok for LGBTQ+ stuff she might want to go to and then suggest that. Even if you’re not sure it’ll be good or fun, it’s a perfect excuse to ask her to check it out with you. Tell her that even if it’s cringe, it might be a funny story and you can grab some fried pickles at a diner afterwards.
Or you can get more specific to her interests. You’ve got her socials. Do some digging. What stuff does she usually go to? Who are her friends?
She could be a nightlife trans woman, who maybe had a great run as a gay guy and who still revels in that environment. She could be an outdoorsy girl who hikes with her queer girl friends on the weekends and loves gym selfies. She could be the more introverted type who wants to whoop your ass at video games all night.
I’d normally avoid going to someone’s house or having someone to your house on a first date, but this is another point trans men have over cis men. It’s not as likely that a woman would “choose the bear” over us. It’s a cliché, and maybe has a dab of sexism to it that we’re not perceived as the same level of dangerous as a cis man, but, hey, it’s okay to use a little societal conditioning to our advantage.
If you do go over there to play Fallout: New Vegas, bring some seltzers or snacks. If she comes to you, have your fridge stocked. Ask her for her drink of choice for Final Fantasy. Check if she’s vegan or gluten-free. And for god’s sake, vacuum up a little.
If you end up going out, and it’s something you’ve attended before and where you see friends, such as queer country line dancing or a monthly trans arts meetup, make sure you introduce her around and keep her engaged in the conversation. Trans people can very easily get lost in the friend zone if you don’t make it clear you’re there together. Keep it romantic with little touches, getting her a drink, or introducing her clearly as your date for the evening. Even among queer friends, make sure she knows she’s not there as just another friend: She’s special to you.
How to Keep It Going
I have been told by my cis male peers that it’s now my responsibility as the man to ask for a follow up date. Unfortunately, this seems to be true because we live in a society. This doesn’t mean you have to plan the whole next thing, but it is on you to say you’d like to see her again and provide at least another suggestion on where to go.
After making sure she got home okay (whether that be after the date or wink wink the next morning), ask if she’d like to see you again. I’ve gotten you this far, now you’re gonna have to do something that cis men have struggled with for millennia: Listen to her.
Every girl is different! As you’re getting to know her, you can pull back from the generalities of both being trans, and find out if you’re compatible beyond that. You have a foundation that puts you leaps and bounds ahead of any cis guy who’s ever tried to pick her up. You’ve got this, my dude. Go get ya girl.
This article appeared first on Lesbian Dating Advice | Autostraddle