#548: I met a cool person to flirt with and I’m scared of what to do next.

Dear Captain Awkward,

So I met a girl last night, one I’ve run into occasionally when the orbits of our respective circles come into gravitational alignment. We spent the time chatting together and exchanged numbers afterwards. I have zero experience with romantic relationships, but what little knowledge I’ve accumulated from rom-coms and trashy novels leads me to believe we mayhavekindofactually been flirting. She’s smart and funny and similarly awkward, and I felt like we connected really well in the short time we had. It’s early stages yet though and I’m in this weird excited for possibilities but desperately trying to play it cool space.

The thing is, I’ve never considered it possible for me to be in a relationship with someone so I’ve never tried. Ever. I’m trans but lodged squarely in the back of the closet (assigned and currently perceived as a guy, wholeheartedly wishing otherwise as a girl). I can’t imagine myself going through with transition though because I have extremely negative self-image, and the first person to laugh at me would crush what remains of my misbegotten soul.

Thus far my motto has been that if I can’t even love myself, how could I begin to love someone else? That way lies jealousy, resentment, and a whole host of Bad Feelings. I couldn’t do that to anyone because I know that I would do that, eventually. Not the best basis for a healthy relationship.

I don’t even know why I’m suddenly considering the possibility, but something about it strikes me as very selfish. Like, doesn’t my not being upfront about being trans constitute deception? I know I’m on shaky ground here because there are a whole bunch of nasty transphobic deception narratives that trans women have to contend with every day and so I shouldn’t propagate or internalise those. But I’m approaching it from the other side; in my nail-studded closet I’m not being true to myself and I’m lying to everyone else. So… deception, right?

This girl, who is by all accounts an awesome person, who is not obliged to be a receptacle for my obsessive worrying (we haven’t even been on a date, for pete’s sake!), who is totally unaware of all this inner turmoil, doesn’t deserve this kind of baggage. What’s more is that like me she has also struggled with depression and social anxiety. I’m terrified of making things worse for her and fatalistically certain I will. How can I start building a relationship with her while witholding such an important self-defining secret, and even if at some point I became comfortable enough to share it with her, what then? Cisgender people are generally not well-known for reacting positively to such admissions.

I don’t want to assume here but statistically speaking she’s likely to be straight (as opposed to bi, or even more unlikely to be gay). When I interact with her (or anybody else for that matter) I don’t put on a big macho act or anything. I’m more or less honest about who I am and what I like/dislike, just with dampened emotions and responses. A restricted version of me, pushed into the neutral zone between genders. Apparently androgyny is in? I’m not going to cross the boundary into masculinity or male-identification, that’s not me and will never be me. But in an ostensibly heterosexual relationship that burden would typically fall upon me and exert all sorts of pressure to conform. On the other hand I can’t really emphasise my femininity or female-identification because a) I’m too scared to do so regardless; and b) it wouldn’t be what she signed up for.

Can you tell I’m an obsessive worrier? We might date and find we don’t gel after all. She could click her teeth for all I know. But if I put myself out there and something special happens, haven’t I created a moral conundrum hammer that’s bound to smash that special thing into teeny tiny pieces? I also wonder if I’m just in love with the idea of love, or being loved, and wish fulfilment is a shitty way to treat someone. Proximity to Valentine’s Day does not help at all, funnily enough.

I don’t know whether to even attempt a romantic relationship with some careful guidelines in place, or to explicitly make it friends-only, or to NEVER SPEAK TO HER AGAIN!!!!!!111 What should I do?

Sincerely,
Faith, Mope, Love?

Dear Faith, Mope, and Love (good nom de plume, btw):

You put Valentine’s Day in your email header, so you get to be the question of today. For past meditations on the day itself, readers should go here or here.

So, Mx. Mope, there are readers who can speak to the specific risks and exhilarations of coming out, experimenting with gender presentation, and dating-while-trans* better than me. There are a bunch of personal stories, great links & resources in the comments here. The fantastic AccidentalBeard discusses coming out here, and our beloved Lt. Trans talks a reader through the fatigue that can come along with a transition here. You are not alone in feeling scared and alone or in imagining what the future will bring with equal parts terror and a secret screaming glee at the prospect of presenting a different side of yourself to the world someday. The fact that you want to be honest with this cute girl before getting involved with her any further speaks well of your considerate nature, but the good Lieutenant has said many, many times that you don’t owe people your entire life story and all your secrets when first meeting them or figuring out if you want to become more deeply involved with them. You’re allowed to test the waters and move at your own pace.

What I can write about with some authority are the common fallacies and worries that you share with other shy daters a.k.a. the reason the “Overthinking It” tag was created.

First dates are practice. Your job right now isn’t to start a serious relationship. Your mission, if you choose to accept it, is to maybe go on one date. The purpose of a first date is to a) meet someone new, or hang out with someone you already know in a one-on-one, let’s-get-to-know-each-other-better context and b) figure out if you want to have a second date. As long as you both show up when you said you would and are basically polite to each other, there is no way to fail at first date.

• If you have a great time and you want there to be a second date, victory!
• If you figure out that you don’t really want a second date, victory!
• If you want a second date and the other person doesn’t (or vice versa), that’s still a victory!
• If you aren’t sure how you feel and think a second date is a good idea if only for information-gathering purposes, that is also a victory!
• If you ask someone on a date and they say no, that is also a victory. You were brave and honest.

In every one of these cases, you will end up with some information that you don’t have now. The information could be “I look hot in that sweater, it’s a good first date sweater.” The information could be “This spot is not conducive to quiet conversation, do not come back here on dates.” The information could be “She clicks her teeth.” Hey, you flirted with someone and have identified someone that you are attracted to and maybe want to go out with sometime = that is a small step toward knowing yourself better. Victory! You flirted! Victory!

If you come home from a very first date with someone you don’t know very well saying “I’m in love! This is The One! Our children’s names will be Unicorn and Placenta!” I’m not gonna tell you you’re wrong to feel giddy and optimistic, but I am gonna caution you to slow down a bit. Your heart and/or groin are galloping way in advance of your head. Maybe let the head catch up and figure out things like “does this person sweep up broken glass on the regular?” before you commit to a lifetime together.

Auditioning and disclosure work both ways. You, my dear Letter Writer, worry that this person might not accept a secret that you don’t even know whether you have fully accepted. Fair! But this is also about you finding out if she is someone you might could trust with that secret someday. Anyone who is potentially a good romantic partner for needs to be, at least:

• Not transphobic
• Bi-curious….ish? Bi-curioush?

There’s a lot of time between “First Date” and “Are We Going To Be A Couple Now?” to feel this lady out on those things, while also figuring out if you laugh at the same stuff and are nice to each other.

There’s a lot of topical stuff that you can refer to without necessarily coming out to her. For instance: Janet Mock’s new book, the twin fierceness of Carmen Carrera & Laverne Cox telling Katie Couric some things, the release of CeCe McDonald and imprisonment of Avery Edison, etc.

I’m not gonna say that these shows are perfect on every front or will be relatable to you, but Jill Soloway’s Transparent is streaming on Amazon Prime and will get picked up if it gets enough votes. Orange is the New Black portrays a romantic relationship where one partner transitioned midstream. These things are out there, being watched, being talked about in mainstream culture. It’s profoundly unfair that any of this should have to be a concern for you, or that one person’s escapist entertainment should have to serve as the carrier for portrayals of your basic humanity. But any lady who has an “ew, gross” reaction to these stories being told or the general idea of transness is not cool enough for you and does not deserve your whole story. 

My boyfriend and I disclosed mental health stuff (Me: depression & anxiety Him: bipolar disorder, I have his permission to write about it) after meeting & really liking each other but before getting serious/exclusive or doing any sexy stuff together. I know it’s not the same, partly because hello, cis privilege! and partly because *other* people in our lives knew this about us, so disclosing to one another didn’t mean creating a vector for a tightly-held secret to come out. And partly because we were on the other side of the worst of it – being diagnosed (hospitalized in his case), several rounds of treating it – and could be secure and comfortable in how we talked about how it affected us. But there was a definite “here’s what you should know before we go any further” discussion.

I don’t know how to construct that moment for you. Maybe it happens with this adorable girl, maybe it’s with someone down the road. But somewhere, sometime, I believe there is a time where you will say “I’m in the very early stages of figuring this out, but I am trans* and I want to be a girl someday” to someone. And hopefully they will say “Okay, tell me all about that.”

There’s coming out, and there is also emotional honesty:

• “I am enjoying spending time with you, but I feel unready for a serious relationship right now.”
• “I am questioning a lot of stuff about myself and my life right now.”
• “I am really new at dating and I need to take things very slow.”

When you feel insecure and shy, it’s easy to get into a mindset where you are the one with something to prove and the other person exists to pass judgment and bestow acceptance, but it works both ways. She doesn’t know it yet, but she has a lot to prove to you before you give your heart and your trust away, and she is going to have her own needs & worries that may or may not match up with yours.

I think it would be a mistake to get deeply involved with someone without telling them who you really are. But I also know that you don’t have to be a final, future-perfect version of yourself to go on one date with a cute girl who seems to really like you. Maybe she’ll be your girlfriend someday. Maybe she’ll be a good friend who shares your journey with you. Maybe you’ll go on a couple dates and make out a few times and then decide it’s all too scary and real, and you’ll have to bail on the dating aspect of things because you’re just not ready. Maybe she’ll break your heart in two and stomp on it in a parking lot outside a depressing bowling alley that you’ve always hated anyway. Maybe she senses and is attracted to all the ways you aren’t like typical guys, and the stuff you are worried she’ll find out is the stuff that is drawing her to you. Maybe she’s secretly trans*/genderqueer/questioning too.

Nobody gets to the good parts of human love and connection by keeping themselves to themselves. There is no magic soulmate out there who will see you once and mysteriously understand and get to know your secret, beautiful self without any risk or vulnerability or effort on your part. To open up is to risk hurt and rejection. In your case, it might be to risk ridicule or violence, and I can’t pretend to understand what that’s like or tell you you should risk those things if you don’t feel comfortable. You are the boss of your own safety and of your own heart.

But I can tell you that one date might be a victory here. I can tell you that I’ve danced at weddings where the drinks are good and the genders are fluid. And I can wish you all the love and hot makeouts and finding your community and your true self in the world.

—————————————-

Moderator Note: Trans* people, people navigating anything to do with coming out and/or gender presentation, we want to hear from you. Cis people, if you have a story about dating a trans* partner that has a happy ending, where you dated happily or became great friends, that might be useful. How did they come out to you? How did you navigate that stuff together? Outside of that, maybe it’s not your thread, and the LW doesn’t need to know your personal dealbreakers, “I could never….”, etc. Those points of view are widely represented and do not need amplification here. My ability to be online will spotty until late tomorrow, so keep it nice.

Second Moderator Note, same as first, a little bit louder, a little bit #@@#$@!#!!!!!!!:

There is a very lovely discussion happening in the thread. I love every comment from a trans*person sharing their story. I love this comment and want to embroider it on a thing, because it is the best valentine the Internet had to offer yesterday. I love the love stories. I want to keep the thread open so the lovely stuff can continue. But after moderating a bunch of comments, we need to set some stronger ground rules:

Armchair linguists who want to discuss pronoun use, like, in the abstract? This is not your thread. If you don’t know what pronoun someone uses, it’s cool to ask “Hey, what pronoun do you prefer?” Whatever they tell you, that’s what you use.

Armchair biologists who want to discuss what gender even, like means? This is not your thread. 

You’ve never thought about trans* issues before? Read. Listen. Learn. Maybe don’t talk. 

Thought experiments about how, if your current romantic interest came out or changed genders, would you want to stay with them? This is not your thread. If that’s not so hypothetical for you, remember, comfort in, dump out.

Staunch defenders of one’s “right” to not be attracted to transgender people? Don’t be attracted to them! In fact, definitely don’t go anywhere near them with your oooooh, so sparkly! perfect amazing attraction. You wouldn’t want to waste it, would you? [The previous sentence may have contained sarcasm] Your personal attraction/lack of attraction/potential attraction is boring and irrelevant. Your need to preemptively announce it is boring and unwelcome.

Staunch defenders of Honesty! Before! All!, your next first date is going to be a very lucky person, I know it! Spot a cute person at a party or in line at the local coffee joint? You can scan Yelp for a good first date place nearby, while, s/he reads your tax returns for the last 5 years, your complete medical records, dental records (+ a full-body scan so they can really “see what they’re getting”), the results of an independent assessment of the cleanliness of your home, written references from your last three lovers, the latest performance evaluation from your employer, a gene scan to determine the viability of any future offspring, and your personal prediction for everything you might do, feel, or become in the next, say, 5-10 years. After all, if you don’t tell a potential date you just met everything about yourself that might help them make a decision about whether they want to date you from the start, you are a lying liar! [The previous sentence may have contained sarcasm]. Without the sarcasm: Your worry about “truth” and “honesty” is concern trolling that you think is masking your discomfort. The mask is not working. Set the thread to “Read Only.”

I love this community, and I really want to assume good faith on everyone’s part, but some of the ignorance on display in the moderation queue is the kind that’s hard to distinguish from harm. This isn’t debate club. This is a vulnerable human being on the threshhold of many exciting adventures asking for reassurance. If your comment can’t center that person, we don’t need to read it.