First Loves, Breakup Guilt, and Rainbows Painted With Watercolors

by Lindsay Miller

I’ve just found out that my very first love is pregnant. I found out through my bff, who is also pregnant. Back in the day, before I knew that these feelings I had for First Love meant I was queer (duh), we three were a posse. First Love and I don’t have contact anymore, except through bff. I am not planning to be pregnant or have kids, and I’m fine with that. I’m also totally in love with my male partner, and have no regrets about giving up things I love about being single, including ladies. Nostalgia, but no regrets. But I’ve been feeling a bit restless the last few months. I have enough experience to know that it’s not really about anything (it feels hormonal, maybe?) so I’m just waiting it out. But restless + I do miss ladies, romantically + First Love + everyone is pregnant but me! They have a special club and I’ll always be the uncool kid (leftover issues from posse-times) = FEELINGS.

I don’t need any advice, as such. It’s fairly minor and I’m dealing fine. I came to the conclusion a long time ago that First Love will always, always give me FEELINGS, and that’s fine. The baby thing, too. None of these feelings are real, true, me-right-now feelings. They’re more road-not-taken, amorphous feelings. But I don’t want to let them spill over into now-me’s life, and I really don’t want to convince myself that I am not happy with my lovely partner, etc, for no real reason. I just wondered if you had some commiserations or words of wisdom for me, because I think not-talking and thinking about it will make the feelings a bigger deal. And I’ve reached the limit of how much I can talk to my partner about them, and I think it’s going to start making him feel vulnerable. Usually I’d talk to my bff, but I just can’t about this one. So … internet lady friends! Can we talk?

It is profoundly weird when your exes start getting married/having kids/otherwise launching Operation Grownup, isn’t it? Even if you’ve known for years that you and she were never going to end up running toward each other in a field of daisies while Ingrid Michaelson performs an impromptu acoustic set, finding out that she is making an actual life-long commitment to another person/fetus can leave you seriously disoriented. It’s kind of like there’s this parallel universe where things worked out between the two of you, and then all of a sudden that universe collapses. And you’re like, “Why is this bugging me so much? I didn’t even live in that universe in the first place.”

You pretty much have your head correct about this whole situation: you love your partner, you’re happy with the choices you’ve made, and you recognize that any path in life necessarily leaves you with options you did not pursue — and, occasionally, a feeling of “what if?” about where those options might have led. You don’t sound like you’re on the verge of leaving your partner, getting yourself accidentally-on-purpose knocked up, or burning down your house and fleeing to Bolivia. You’re just having some fairly normal emotional reactions to realizing that you’re an adult and there are some things you probably won’t get to do. It’s fine, everyone goes through it.

Just because it’s normal, though, doesn’t mean that your only option is to cowgirl up and wait it out in silence. You’re unhappy, and that sucks, so let’s try and find a way for you to be happier, okay? I really think you should reconsider ruling out your BFF as a confidante. Especially since you’re trying not to unload all this onto your partner (which seems reasonable, as an ongoing monologue about your FEELINGS for someone you used to boink is likely to leave him with some FEELINGS of his own), you could use a non-Internet person in your life to whom you can spill your guts. I know it’s hard, since she’s part of the issue that’s weighing you down, but she’s your best friend and she loves you — she’ll hear you out. Just don’t make it into a blame thing, like “you guys went and got knocked up at the same time and you didn’t even invite me.” Stick to those ever-useful I statements — I feel left out, I feel nostalgic, I feel like if I don’t eat some pussy in the next five minutes my brain is going to melt out my ears. Maybe she’ll have some useful advice, maybe she’ll just listen. Either way, I suspect it would be good for you to get all this off your chest in a face-to-face way.

Whether or not you decide that’s an option, the Hairpin is here for you! Commenters, what have you got? Encouragement, sympathy, Internet margaritas? Go! (And then come back here and read the rest of the column, please. I work so hard.)

I’m a straight girl with a crush on a trans guy. This question is still very hypothetical, as I haven’t actually, er, spoken to him or anything, but he’s friends with some friends of mine so it’s not inconceivable that I may have a chance to flirt with him at some point in the future (I have seen him dance shirtless however, my GOD dancer boys are hot. Anyways).

So I guess I have two questions, the first being the most important. I am very attracted to this guy, but I am a little unsure of whether I could ever be totally sexually satisfied in a relationship where there’s no penis involved (my sleuthing among friends has suggested he’s had surgery on his chest area but not the nether regions, no idea whether he intends to get the 2nd surgery or not). I am totally down to experiment with strap-ons or whatever else there is and see if I could be happy with that, and I think it’s definitely possible. But I’m worried about what would happen if it turned out I couldn’t be sexually satisfied in the relationship. I can imagine that for a trans person, getting intimate with someone only to be told ‘sorry, you’re great but your junk just ain’t doin’ it for me’ could be really devastating. Would I be a total asshole to pursue him if there’s a chance that might be what happens?

The second question, I feel embarrassed to ask and I hope I’m not being totally ignorant, but … how DO trans guys who haven’t had surgery generally handle sex? If there is any ‘general’ answer? Are they for the most part comfortable having the genitalia they were born with stimulated, or do they avoid it? All I have to go on in this realm is a trans guy friend who mentioned in passing that him and his girlfriend were mostly pegging, but I have no idea if that’s typical or what.

I would very much appreciate your advice on this matter, so that the next time I see him I can with confidence proceed to awkwardly attempt to flirt with him and find out if he has any interest in putting his face on my face.

You haven’t ever spoken to him, but you’ve already got your friends asking around after the contents of his boxers? Girl, I’m concerned that you’re Fredding out a little. Your imaginary relationship with this guy has gotten way ahead of reality. Take a few deep breaths. While you’re doing that, try to come to peace with the possibility that the fantasy you’ve built up around this guy might not in any way resemble the person he is in real life, so you don’t end up caught by surprise and resentful when (if) you actually get to know him.

Also, I hate to come out of the gate scolding you, but I’m not super comfortable with the idea that, because dude is trans, it’s fine for his friends to hand out personal information and medical history to anyone who asks. Our culture just loves to deny trans people their privacy, often on the basis that otherwise they would use nefarious means to “trick” people into dating/sleeping with/using a public restroom at the same time as them, and it is bullshit. A person’s specific genital configuration is something that only needs to be shared with his (actual, not prospective) romantic or sexual partners — disclosing to anyone else should happen at his discretion or not at all. His gender and body are none of your business unless he decides they are. If you intend to pursue this guy romantically, it needs to be with sensitivity and respect. No more snooping, okay? I’m sorry for being hard on you, but I really am on your side — I want you to get the cute boy, and you’ll have a better chance if you don’t make a big fat deal about his gender. I’m just trying to get you laid, darlin’.

On to the specifics of bumping and grinding: this is your basic good news/bad news situation. The bad news is that I can’t tell you how your crush wants to get down. The good news is that there is a whole thrilling, surprising, slippery world of possibilities waiting to be explored. There are no hard and fast rules for what trans people like to do in bed — they are every bit as sexually diverse as cis people, and just as likely to have unexpected kinks, hangups, or moles. He might have a strap-on, he might not. He might want to have his bits fondled, he might not. As you do with any new sex partner (right?), you should be prepared to roll with something that’s new to you, to speak up if you feel uncomfortable, and to make sure he’s comfortable every time you want to go further. It’s often standard practice among trans people and the people that love them to ask “What can I touch?” the first time you get somebody naked, which is an excellent idea and should really be adopted among all the people, everywhere, at all times. There’s no reason to assume that you know what kind of sex someone wants just because you know their sex, gender, orientation, or favorite Hunger Games character — sleeping with someone new should be a process of discovering each other, not hauling out the same moves you used on your ex.

Should you in fact work up the nerve to talk to this boy, and (fingers crossed) end up doing some horizontal makeouts, you should either a) ask him what he wants or b) tell him what you want. If you’re more or less in agreement, go from there. And, if you do hook up with him, and it turns out that the lack of a flesh-and-blood penis is a dealbreaker, it’s fine to just say “You’re great but I don’t think we’re compatible,” and move on. The problem is not his junk, it’s just that you two aren’t clicking. If you are clicking — if you’re giving each other amazing orgasms and can’t keep your hands off each other — then his vagina is simply not going to be a problem.

Also, you should check out this poem by my friend, the talented and gorgeous (and single, lllllladies) Gabe Moses, entitled “How to Make Love to a Trans Person.” It is so lovely.

A few months ago I realized that I was really super attracted to one of my girl friends who I knew was also attracted to me. I’d never been attracted to a lady before, so I talked to my boyfriend (it’s probably relevant to mention that we were in a long term, long distance relationship) about it and he encouraged me to pursue things with her physically. I was very confident that it wouldn’t come between the two of us, and since he was the one who initiated the talk about me pursuing my friend I figured he was genuinely okay with it too.

I talked to my friend about how incredibly sexy I thought she was. She’d already picked up on my vibes (before I even realized that I had vibes) so it was no shock to her. The first time we slept together I heard a click in my head. The click said, “Hey you! You should have been doing girls all along!” It took me about a month and a visit to see my boyfriend to realize that I was not a 3 on The Kinsey Scale, but somewhere around 5. I’m a deliberate person. I think about things from every possible angle before I make a decision. But with this there was no decision to make. Of course you, A Queer Chick, you already know that.

So I talked to my boyfriend about it and we broke up. We’d been together for almost three years and two of those had been long distance. We put a lot of effort into keeping our relationship going and we saw ourselves together for the long haul. I know this break up has been really hard on him. I feel terrible for hurting him. I still love him very much and still see him as one of my best friends, but the thought of sex with a guy makes me feel obligated and very panicky and, if not a little grossed out, generally perplexed. If it weren’t for his understanding and support during the time I was discovering my queerness, and in fact for how comfortable he helped me feel with my own body and sexuality during our whole relationship, I don’t know when I would have realized that I am gay. He’s helped me with this amazing life changing realization, and all I’ve done is break the heart of someone that I deeply care about. I feel like scum. I keep trying to think of a way to have done things better. I guess I can’t change the way I approached things now, but is there anything I can do to make this easier on either of us? We talk pretty regularly through text or e-mail. It’s hard to enjoy the shiny new lesbian part of myself, or anything really, when I know he’s hurting and it’s essentially my fault.

I hate to tell you this, but there is exactly one thing you can do to make things easier on your ex, and it’s going to make things much harder for you. You know that texting and e-mailing you’ve been doing on the regular? Yeah, you need to cut that shit out.

Someday, my wonderful new-minted fellow queer chick, you are going to be in a relationship with someone you love deeply, and she is going to smash your heart to smithereens out of fucking nowhere. It will be brutal. You’ll walk around in a daze. And then that person, the one who has just destroyed you emotionally and left you a hollow, insomniac, wine-guzzling, sad-movie-watching shell of a human being, will tell you that she wants to be friends, and can we grab coffee and chit-chat later this week? So you’ll brush your hair and stare at your dead eyes in the mirror and force yourself to smile and pretend like you’re not screaming on the inside because being in the same room as her is better than nothing at all, even if it does feel like ripping off a scab over and over again for a solid hour. Do you see where I’m going with this?

Your breakup was hard for you because it took away a source of stability in your life and left you with all these icky feelings of guilt, but it didn’t break your heart. You still have basically the relationship you want with your ex-boyfriend: you’re close, you talk, he supports you emotionally, and you get to have sex with girls! What’s not to like? But you have to realize that, if he was in love with you — and it sounds like he was — being friends right now feels to him like being repeatedly hit in the face with a sock full of “this is what you will never have again.”

There is nothing you can do that will remedy the pain you’ve already caused him. This doesn’t mean you should torture yourself forever — you did the right thing for both of you by ending it when you realized you weren’t satisfied. Still, the only thing you can give him at this point is the time he needs to heal. He is probably never going to tell you to stop texting him, because he wants to be close to you in any way he can, no matter how painful; that’s why, horribly and unfairly, cutting off contact has to be your job. If the two of you are ever going to have a real friendship, you’ve got to let him get over you, which he’s not going to do if you’re talking every day.

It’s going to hurt like a bitch in the short term, but I really think what you need to do is tell him that you both need space to process your breakup and that you shouldn’t talk for some specified length of time — say, three months. Then stick to it. Resist the urge to email him when you’ve had a bad day, or text him a picture of the guy with ridiculous hair at the coffee shop. This will give you the chance to have some fun and hook up with some girls, which is your Constitutional right as a newly-out homo; and it will give him the chance to mend his broken heart in peace.

And when the interval you’ve agreed upon is over, you have to wait for him to get in touch with you. As the more-wounded party, he gets to decide how much of a relationship he wants the two of you to have, and on what timeline. That may mean he calls you in three months and fifteen minutes, dying to tell you about his hot new girlfriend; it may mean he texts you in six months to say “what’s up”; and I’m sorry to say it may mean that you never hear from him again. He might decide that he won’t be able to rebuild his life if he’s constantly being reminded of what he’s lost, and if that’s where he ends up, you need to respect it.

Here’s hoping he thinks it over, decides you were never really that hot to begin with, and you two can be best buddies again.

All right, A Queer Chick, I got one for you. I’m 99% sure that my sister falls somewhere on the GLBT spectrum (we’re both in our late 20s, if that’s at all relevant). I’ve always thought she leaned more towards being attracted to women — I guess it’s one of those things you just know? And after being exposed to stories of trans youth, I’m startin’ — to wonder if a lot of the behaviors she exhibited growing up were actually more signs of her having gender identity issues. Either way, wherever she identifies on that spectrum is fine. But she’s never said anything to me or my family, despite how openly okay we are with it. Growing up, my mom was one of those artsy hippie people that actually had like rainbows painted with watercolors with diversity sayings written underneath them. And while I think I have slightly better taste in artwork, the apple didn’t fall far from the tree here, and I show it and talk about it pretty openly. Seriously, you’d be hard-pressed to find a household more accepting of a gay family member than my immediate family.

The thing is, my family is pretty small and none of us are that close. We all have our separate lives and are physically together for about a couple hours a year (partly due to geography). I talk to my sister the least out of any of them because she’s one of the most miserable, unpleasant people I know. She’s constantly negative, criticizes everyone, has anger management issue, and is generally an emotional drain on everyone. And I’m starting to wonder if those two are connected, that maybe she doesn’t feel like she can be herself or that she’s uncomfortable in her own skin, so she’s lashing out or pushing people away?

Now, I’m a big believer in that it’s her own decision when and to whom she comes out, and if she’s not ready to tell other people or maybe because she’s not comfortable with the information herself yet, that’s fine. And my role as a supportive family member is just to make the environment as accepting as possible for her when (and if) she’s ready to come out. But after years of sharing GLBT advocacy articles on our overlapping online social networks and talking about my gay friends, I don’t know what else I can do. And if her coming out of the closet and being comfortable with who she is will make her a more pleasant person, man, we could all really use it. So, my question to you, A Queer Chick, is how can us straight allies help our closeted friends and family feel comfortable enough to come out? Is it ever really appropriate to send her an unprovoked private message on Facebook just saying “Dude, seriously, it’s okay if you’re gay or if you’re not! It makes no difference either way!” because someday when I’m drunk, I just might do it.

Oh my God, sweetheart, I know your heart is in the right place, but please do not do that. Don’t. Do not. That thing you are considering doing? It is definitely not a thing you should do.

Here’s the problem: you and your sister are not close. You don’t particularly like her, and you don’t particularly talk. It sounds like you have valid reasons not to like her, but that doesn’t change the fact that you are not the person she turns to when she has worries. If I were your sister, you’d be way down on my list of people to come out to. Assuming that she is struggling with some kind of secret, whether it’s orientation, gender, or something else entirely, she’s probably in no hurry to hash it out with you if she perceives you as unsympathetic or disinterested.

If your sister is queer, and you push her into coming out before she’s ready, she is likely to resent you for it. She will feel pressured, invaded, disrespected — because demanding information she doesn’t want to give you yet is pressuring, invasive, and disrespectful. Sending that drunken Facebook message could make her go “Oh my God, you’re right, I’m a total lesbo, it feels so good to get it off my chest!” But there’s a much better chance that it will do long-lasting damage to your relationship. Deciding when to come out is intensely personal, and forcing her into it could cause wounds that will take years to heal. Not to mention that if she’s not queer, she will probably be less than amused by your attempt to diagnose her sexuality.

The best thing you can do, if you ever want your sister to feel comfortable coming out, is try to improve your relationship — reach out to her, call more often, make an effort to be part of each other’s lives. If you don’t feel like this will be worth your while, that’s fine, but it’s the only way you’re ever going to be privy to what’s going on in her heart/vagina. Your sister already knows that you like and accept gay people. Now you need to show her that you like and accept her.

Previously: Femme Baldness and “INEXTINGUISHIBLE PASSION.”

Lindsay Miller knows everything (and is now on Twitter!). Do you have a question for A Queer Chick? (300-word max, please.)

Photo by Anna Sedneva, via Shutterstock