Filed Nails, When to Move, and the Coded Mixtape

by Lindsay Miller

So, Queer Chick, I come to you as a supplicant. I’m a trans guy who’s looking to start dating following a cross-country move to begin grad school. This is all good, except for a few complicating factors. A) I’m pretty much 100% out by choice. Googling my name outs me as trans within the first page. I’d like to think anyone I’m involved with would be down with that, but I recognize this could scare off possible partners. B) Ever since I came out five-ish years ago, I’ve basically been 100% inactive on the dating front for various reasons. That puts me in my mid-twenties with almost no adult dating/sex experience, especially as a dude who is primarily interested in ladies but not opposed to dudes. C) I’m legendarily oblivious. I have to be told in very small words if someone is interested in me (in part as a result of a lifetime of very low self-esteem).

So, basically, I’m kind of terrible at this stuff and have no idea where to start. Any advice?

Yes, I do have advice! It’s around here somewhere. Um … this piece of paper says “file your nails before fisting.” Not really a direct answer to any of your questions, but always good to keep in mind.

On to the advice that’s specific to you: how do you start dating, as an adult who is trans and bad at picking up hints? Fortunately, you have access to one of the universe’s best Get A Date Fast cheat codes: you’re in grad school. Your mileage may vary depending on your specific field of study, but if I may make a sweeping generalization here, grad students are just slutty as hell. They’re working hard, putting in long hours for little pay or no pay or the ever-popular negative pay, usually on projects so specialized they’ve given up trying to explain them to anyone outside their department; they’re stressed, looking for a way to blow off steam, and there you are all cute and available and totally in agreement about the use of shifting perspective in experimental post-colonial literature, and next thing you know your boxer briefs are hanging from the ceiling fan.

At the very least, you’re definitely going to get hit on, as long as you have the most basic grasp on social interactions and hygiene. But how do you tell when you’re getting hit on? I can’t give you a foolproof road map to figuring out whether that cute lady (or dude) is feeling it; one person’s “take me now” is another’s “just being friendly,” so in general I advise that you assume nothing until her tongue is in your mouth.

Don’t drive yourself crazy trying to figure out what someone’s signals mean. Instead, what you should do is clearly and unambiguously make a move on anyone you find attractive. I don’t mean give them meaningful smiles and “accidentally” brush your elbow against theirs; I mean walk up to them and say “I’d like to take you out to dinner on Friday. Are you free?” They will either say yes, which means they’re interested, or no, which means they’re not. This approach is terrifying, but it really does take all the guesswork out of flirting.

As far as how you disclose your gender history to new folks and potential makeout buddies: Being out to everyone, which it sounds like you’re pretty comfortable with, certainly saves you the trouble of having The Talk with anyone you want to date. If they already know, and they’re not into it, they’ll just say “no” when you ask them out. This will be no more painful than any other rejection, by which I mean it will ruin your life for weeks. But anyone who’s really feeling you won’t be deterred by the knowledge that you’re trans — it will just be one more thing they dig about you, like your eyelashes or your habit of making really dorky puns. Have an awesome time, and if at all possible, avoid sleeping with your professors.

I’m severely emotionally entangled with one of my closest friends and it’s gotten to the point where I need outside help to sort it out. I’m a junior in college and came out to myself a year and a half ago when, over Christmas break, I kept forcing myself to send trite “miss you lotsss xoxoxo” texts to my unfortunate bf while obsessively thinking about the soprano section leader in my choir (the aforementioned close friend) and finally figured out that that wasn’t normal. That close friend was also the only queer girl I had ever met in my life and the only person I could talk to about how absolutely fucking terrified I was about potentially being gay. She was the first person I came out to, and the only person to know for four months.

Fast forward to choir tour that April when it’s 3 a.m. and I’m perched on the edge of a hotel bathtub in DC writing a short, awkward, apologetic note telling her that that crush I had been hurting over? Was her. I slipped it into her choir folder, because that’s what choir people in love do. And she took me aside after rehearsal and hugged me and told me that she wasn’t into me that way but that it was all right and that I would find someone better and that we were still best friends, right?

And then, for the choir mix tape swap, she got me by luck of the draw, and made me a mix tape that was ¾ awesome music because she knows me really well and ¼, well, it was really hard not to read some reciprocated feelings into it. Highlights include “What You Never Know (won’t hurt you)” by Hayley Westenra. She was graduating that May to go 10 hours away to grad school, I’m two years younger.

She and I pretended the CD never happened. We stayed friends. We chat for hours late at night on AIM where she calls me pet names and sometimes says she loves me (and a few of her other friends, completely platonically, you know) and I try to figure out a way to hate her / to stop loving her. But can’t. Even when she got a boyfriend and asked me for advice (she’s bi).

What do I do? Do I confess that I’m not over her? Do I stop talking to her — and by that take away the only person I can talk music and queer things to? Do I keep my mouth shut and just let it build up / hope it dies away eventually? Have I mentioned she has a boyfriend? I’m so screwed.

I’m sorry to tell you this, darlin’, but the reason you’re screwed is that you’re continuing to hold out false hope for this relationship. Let’s go to the scoreboard, shall we?

She loves you:

– She made you a mix CD with a potentially suggestive song on it one time (2 points)

– She calls you pet names, the way a girlfriend would, or a waitress, or an Internet advice columnist who calls everybody “darlin’” (2 points)

– She has been known to be attracted to girls, and you’re a girl (0 points, come on)

She loves you not:

– She has a boyfriend (10 points)

– You told her you were in love with her and she said she didn’t want to date you (infinity points)

Sadly, the math is pretty clear on this one. You gave her a green light and she didn’t go for it, which is the universal signal for “not into you.” Once that’s happened, you no longer need to waste your valuable time deciphering her song selections and late-night phone calls. You’re driving yourself crazy because you haven’t let go of the hope that she is nurturing a secret boner for you, but the second you get it through your head that she’s not — that there is no possible future where the two of you end up together — well, you won’t suddenly be over her, but you’ll definitely be moving in that direction.

What’s more, when you give up on her, you’ll finally be open to the possibility of falling for another girl. And as we all know, the best way to get over someone is to have your heart stomped into a brand new shape by someone else.

I’m in my early 20s and living on my own in a pretty backwater part of a Midwest state. I hate it. I loathe it. When I visit other places that are not this place, I cry before I have to go back. I am so miserable and up until about eight months ago, I was at least dating a girl (long distance, because apparently I am an idiot) who I was very much in love with. Now I’m single and bitter about it, and trying to look for love in all the wrong places.

The thing is with this town: it’s really backward. I’ve gone to the gay bar and found no one I’m interested in. I briefly dated a girl but she ended up being pro-life. OkCupid has been a fruitless endeavor. Are my dealbreakers inhibiting me from ever getting laid ever again?

I don’t want to be with anyone more than a year younger than me, but not significantly older than me either, I don’t want to date anyone with kids or anyone who is dating a man who allows her to “mess around” with women. I don’t want to date racists. This has surprisingly (or unsurprisingly?) hampered me from dating at all. My question is: are my standards too high? I’m trying to value myself and make other people recognize that I am totally a catch, but am I just being a snob?

Okay, you started with “I’m miserable where I live” and then took a hard left into “am I too picky about women?” We’ll come back to the women thing in a moment (short answer: possibly!), but let’s talk about your hometown first.

Girl, move already. You know how I can tell you need to move? You didn’t even try to convince me you don’t need to move. You didn’t talk about your awesome job, or how you love living so close to your sister, or how the Ethiopian place down the street delivers for free. If you’re not offering a list of reasons you have to stay where you are, my guess is that there aren’t any, or at least none that you think are worth considering. That means the only thing keeping you there is inertia, and you need to shake that shit off. Yes, moving is horrifically stressful and expensive, and yes, right now is a crappy time to be looking for a job, but do it anyway. If nothing else, do it because it will help you get laid. You’re never going to find a healthy relationship if you’re constantly bitter and depressed because you hate where you live.

Now, after you move, or while you’re saving up for a deposit on a new place, you’re still going to want to find a lady friend. At that point, you may want to reconsider whether your list of requirements is too stringent. There’s nothing wrong with refusing to date people whose political beliefs are offensive to you, or people who aren’t monogamous if you are, and obviously you should not ever date racists. And there’s nothing wrong, ever, with refusing to date someone who just doesn’t do it for you. You should absolutely hold out for the person who excites you and charms you and turns you on and makes you grin like an idiot every time you think about her.

But be willing to look around a little until you find her. Who knows? She might be a year and three months younger than you. She might be hanging out at the gay bar, but you didn’t meet her because you went on trivia night but she always goes to the open mic. She might be that girl you dismissed out of hand because she had a stupid haircut. Give people chances, and eventually one of them will turn out to be worth it.

I have the perfect boyfriend. He’s handsome, smart, ambitious, funny, and wants a future with me. A lot of girls are jealous that I have the man that I do. And many girls are after him. I care about him — and do love him deeply. But here’s where the problem lies. In the bedroom. Every time we have sex, in order for me to orgasm, I think about women. I masturbate to the thought of women. When he goes down on me, I think about women. Deep down inside me I can’t help but wonder if I’m gay. I’ve had relationships with women before but they never seemed to work. I feel stuck and confused. He knows I’m bi-sexual and he’s been very clear that he doesn’t want to share. We have now lived together for the past two months — and I find myself sad often, crying, wondering if I made the right decision. Please help!

Oh, sweetheart. Let’s start with the most important thing: if you are sad and crying all the time since moving in with your boyfriend, you should not be living with your boyfriend. Whether or not you’re gay (and, uh, it sure sounds like you’re gay), you’re clearly very unhappy in your relationship, and you need to do some reevaluating. Yes, adjusting to living together can be stressful, and is often a period of increased tension, but this isn’t “oh my god if you leave your shoes in the middle of the floor one more time I’m setting them on fire,” this is “I don’t feel right in this relationship, and it’s making me miserable.”

Just because he’s handsome, smart, ambitious, and funny does not mean he’s the right partner for you. Plenty of people have those qualities, and if you tried to bone all of them you would end up in jail or in the hospital. And just because other women are waiting in line to snatch him up definitely does not mean he’s the right partner for you. “If I put down this toy, someone else will grab it, so I have to keep playing with it forever” is toddler logic — you’re better than that.

You say you love him, and I don’t want to tell you your feelings aren’t real, but it’s not unheard of for people in failing long-term relationships to use “I love him” as shorthand for “I’m afraid of losing the stability he provides me, I don’t want to be alone, and I’d feel bad about hurting him.” But none of that is a good reason to stay with someone who doesn’t make you happy. Finally (this is the part that really, really sucks) even if you love him, that doesn’t necessarily mean he’s right for you. Love isn’t always enough. Sometimes people who love each other have to break it off, for a variety of reasons including but not limited to someone realizing that she’s gay.

I think you need to listen to your heart/vagina, because it sounds to me like what it’s telling you is “Get me out of here.” If it’s time for you to leave, start packing. And then, after an appropriate period of mourning has passed, ask out some girl and see where it goes. Yes, none of your relationships with women have worked out before, but that’s pretty much going to be true of every relationship right up until you meet The Last Person You’ll Ever See Naked. I can’t tell you when that will happen, but I think you already know that your boyfriend isn’t it.

Whatever you do, please just remember that no matter how great your relationship looks on paper, that means jack if it’s not making you happy. We’re not grading on a curve here — “better than anyone I’ve dated in the past” does not round up to “good enough.” It’s not good enough unless it’s fucking awesome. And you’re going to find that eventually. Probably — I’m just saying — with a girl.

Previously: Second Favorites, Gold Stars, and Sex Not Had.

Lindsay Miller is also on Twitter. Do you have a question for her?

Photo by Anna Sedneva, via Shutterstock