How to Have a Boyfriend, “Advanced Dating,” and Girls With Short Hair

by Lindsay Miller


My girlfriend of over a year recently came out to me as a trans man. I’ve never been in a relationship with a man before: not because I’m unattracted to men — -I am sometimes! — -but because I’ve always preferred the company of women, and I love the queer community. I love my partner and support him and I want to stay with him, but I never thought I’d have a boyfriend, and I need some advice on how to proceed.

My boyfriend has told me that he still sees himself as queer, and that we’re still a queer couple, and he intends to be open with friends and family about his identity as a trans man. That was a huge relief to me — -I think it would have been a dealbreaker if he’d told me he wanted to pass as a straight couple all the time. But what can we do to make our relationship feel like a queer relationship still? How can I still be visible as a queer person when I’m with a man? I’m pretty femme, and usually the only way I’ve ever gotten recognized as queer is when I’m out with a girlfriend. For years I’ve used the “mention your girlfriend” tactic as a way to come out to people, because coming out still terrifies me, every time. I can’t do that anymore.

Suddenly all the normal, everyday things of our relationship feel different, and I’m finding myself obsessing over the gender dynamics of every little thing, in a way I never did before, when I saw this as a relationship between two women. How can I get over that? I don’t know how to be in a relationship with a man.

A lot of this is compounded by the fact that we’re about to move together to a new city where we know very few people. We have a great community of queer friends where we live now, but we’re going to be starting over again in a few months from scratch. Making new friends is hard enough — -now I’m worried about making new friends who also see us as a queer couple. Please help me! I want to keep my queer community, but I also want to respect my partner’s gender identity. I don’t want anything to change in our relationship, but I know everything is going to. What can I do?

You’re worried about two distinct things here — -how your boyfriend’s transition affects your relationship, and how it affects your public identity as a queer person. Try to keep them separated in your head, because they require different approaches, and you don’t want your “but how will people know I’m queer” concerns to spill over into your actual relationship.

Let’s start with the just-the-two-of-you stuff. You say you don’t know how to be in a relationship with a man, but you’ve had a year-plus to learn how to be in a relationship with this man, and that’s all that matters. There are at least as many right ways to date a dude as there are dudes. If nothing has changed in your relationship besides his honesty about his gender — -if he still treats you with love and respect, if you still have fun together and are attracted to each other — -then I don’t see any need for revisions. Don’t get up in your head about How To Have A Boyfriend. You’re already doing it! If there wasn’t a problem in the power dynamics of your relationship before, there probably isn’t one now. (If there was always a problem and you’re only just now noticing it because you were taught that manipulation and abuse only happen in straight relationships, I’m really sorry and you should definitely bail, but it doesn’t really sound like that’s your situation.)

It’s also possible that his behavior has changed somewhat, or will, now that he feels free to be who he is — -if he’s been performing “lady” up until now, you might notice certain differences around the house as he settles into a more natural way of being. Then again, you might not.

There’s also the possibility that hormones, if he’s on them or plans to start them, will alter his temperament. The best way to deal with this is to be honest with each other and keep communication open as you work through it. Again, whatever challenges you end up facing will be between the two of you, and you’ll deal with them — -or not — -more or less the way you always have; him being a dude doesn’t change things all that much. You don’t have to be like, “As a woman in a relationship with a man, the next time you leave the ice cream on the counter until it melts I’m going to pour all of it into your sock drawer.”

On to the public side of things. I’ve got great news for you: Being a queer person is not a status conferred upon you by the gender of your partner — -the power was inside you all along. I know that it doesn’t always feel that way (I, too, am a femme queer person, and I understand that with great invisibility comes great insecurity), but you have to trust that anyone who erases your queerness because you’re dating a dude is the one with the problem, not you. Queer identity is your identity. Queer community is your community. There are lots of queer / bi / pansexual ladies who sometimes date dudes, and yes, they sometimes have to push a little harder to get the recognition they deserve, but queerness is ultimately about who you are, not whether the person you smooch can grow a beard.

When you move to your new city, make a point of attending queer events and getting to know queer people. If anyone questions your identity, explain that you’re attracted to people of more than one gender and thus you belong there every bit as much as they do, and if they have a problem with it, they can just sit out the next bisexual knitting circle. Don’t make it about your partner’s gender. He doesn’t determine who you are. You do.

I’m a bisexual queer lady in my early 30s. I’m open to dating anyone. This has sometimes lead me down rough paths when I say “no” to first dates since I’m well known to go out a few times with most people that ask or I feel like pursuing. Because while I am friendly and flirty that way, I am no one’s “very-first-date-ever” person. I’m waaay too advanced for beginning daters. You’ve got to level grind a bit before you can ride my ride.

This leads me into my problem.

One of my friends, we’ve gotten close over recent years. She is somewhere on the asexual spectrum. She does not and has not dated. We’ve talked about it some, but she is private about it to the point of rarely speaking about her sexuality. Which, cool beans! I relate. I’m incredibly private in other areas of my life.

What used to always be group outings with friends have evolved into us going out fairly regularly one-on-one. Dinner, movies, shopping, every day things, even some holidays spent with each other’s family. We talk every day, through email or text, see each other in person regularly, even if it does not exactly work in our schedules. She has gone out of her way to help me out in situations, the same I have done for her. She refers to herself as my beard, as she has acted as my fake girlfriend on several occasions over the years (you know when you have politely brushed someone off, said no, then bluntly said no, then faked it with someone else?). If I don’t fight her for the check, she always pays for me. We hold hands sometimes, even snuggle. We kiss on the cheek regularly.

I don’t mind any of this! We are close friends. I also have a horrible, horrible crush. And I’m not sure where our intimate friendship ends and maybe something else begins? If it even is something else? I want to talk about it with someone, but also afraid to out my crush because, while they are my friends, they will share because OMG, WE MIGHT GET FOR REALZ TOGETHER? (That is not what helping means, friends!)

I want to talk about it with her, but am also leery I am seeing what is an awesome, intimate friendship as something else through my crush-filled romantic eyes. I don’t want to ruin our friendship. I am an adult that can pull up my big girl panties and get over my crush, so I am afraid to voice this out loud. I mean, how do I ask “are we dating and I missed something?” or “am I your squish?” And again, she does not date nor has dated. If there is something, I’m afraid I’ll just mess it all up since I am, again, too advanced of a person to be someone’s first date friend.

I’m totally out of my depth here, which I didn’t think I would experience again after my college days!

Wait, I’m super curious what this “advanced dating” you’re talking about entails. What kind of crazy high-level romance do you require? Do you live in a cave on the side of a cliff that your dates can only approach by climbing a rope ladder, gripping a bouquet of roses in their teeth? PLEASE ELABORATE.

Honestly, I don’t think dating is very much like, say, mountain biking, where you can’t really do it with someone unless they’re about as experienced as you are. Every time you date a new person, you have to learn how to do it all over again, adapting to their specific preferences and peeves and weird habits. Sure, sometimes it takes a few (or a hundred) tries to figure out what you’re really looking for, but sometimes you get lucky right out the gate — -and neither of those things depends on how experienced your partner is.

I’m trying to figure out what it might mean to be an “advanced date,” and I’m wondering if this is some kind of hangover a past partner (or multiple past partners) telling you that you were “too much” or “too challenging” for them. A lot of people go through this, especially women, especially smart, passionate, interesting women who date men. There is, unfortunately, a large population of folks out there in the dating world who want their partners to have no needs or insecurities or hangups or ambitions, who think they can have romance with absolutely no conflict, who are basically looking for a coat rack they can make out with sometimes. Let’s be clear: Expecting this in a date is a character flaw, not a lack of experience.

Some people — -I’m gonna be optimistic and go with “most people” — -enter the dating pool already knowing they will have to communicate and compromise in order to find love. If you meet such a person and the two of you have chemistry, I don’t see any reason not to go for it, even if they’re new to the taking out of ladies.

Now, whether that applies to your umfriend (for the newcomers: a person with whom you have an undefined but potentially romantic and/or sexual relationship, as in “This is Tasha. She’s my, um, friend”) is a different question — -and one that, I’m sorry to say, can only be resolved by talking to her. It definitely sounds to me like you two have Some Kind Of Thing Going On, but I can’t tell you what that is. You’re going to have to come clean about your feelings, your desire to date her, and your confusion about whether you started dating way back without even noticing it.

I know you’re concerned that being honest could hurt your friendship, but going on without knowing where you stand will also do damage. Tell her how you feel and what you want, and listen to what she wants. It’s possible that she hasn’t dated because she has no desire to date, period; it’s also possible that she just hadn’t met anyone that she liked as much as you. Either way, a frank conversation will let you both know where you stand. And if she’s not into it, you’ll be able to start getting over your crush without wondering what might have been.

I tend to only be attracted to women who present as masculine-of-center and I have a hard time explaining this to others and to myself. I identify strongly as femme (I feel uncomfortable in pants and flats) and I love the idea of the old school butch/femme dynamic. The idea of sleeping with a girl who has long hair, wears make-up and can walk in high-heels doesn’t turn me on in the slightest. But I have a hard time justifying this. Wouldn’t a “real” lesbian be attracted to women in general, regardless of how they dress and carry themselves? I identify as bisexual and I’m also attracted to, but very self-conscious around, men. Perhaps I’m secretly straight, and only using masculine women as stepping stones? Or perhaps my butch-only attraction is a defense mechanism that I concocted long ago to reassure my straight college roommates/friends that they were safe around me? My last girlfriend identified as androgynous, and it made her uncomfortable that I was more attracted to her when she wore button downs and kept her hair short. Of course, I was in love, and I would have continued to be in love if she’d started wearing dresses, but it is true that my feelings of desire would’ve become complicated. I feel like perhaps it’s wrong that my attraction is so much more about gender presentation than it is about gender. Because isn’t there, ultimately, a glorification of the patriarchy inherent in the classic butch/femme pairing? I feel like lesbian couples with more fluid gender roles (where, say, both partners are androgynous) are somehow more politically progressive and advanced than I am. Is it ok to only like girls with short hair? Or is this something I need to work on in myself?

It’s totally okay to only like girls with short hair. As a femme married to a biker butch (who’s also a gourmet cook and amazing knitter, so fuck the idea that gender roles define every aspect of your life), I don’t agree that butch-femme relationships inherently “glorify the patriarchy” any more than femme-femme or, for that matter, dude-lady relationships. If there’s no assumption that the more masculine partner is more capable, more intelligent, or should have more power within the couple, then a romance where one person is feminine and the other masculine — -regardless of their genders — -is in no way politically regressive. There’s also no reason to assume that a “real” lesbian would be attracted to every woman in the world regardless of gender presentation, appearance, or personality. Jesus, that would be exhausting.

Still, though your Butches-Only predilections are totally valid and nothing to be ashamed of, it’s probably worth examining the reasons behind them. Western society, including the queer community, tends to overvalue masculinity and devalue femininity, and our sexual preferences are informed by the culture that surrounds us. If there’s a part of you that believes femmes are somehow less valuable than butches and that’s why you’re not interested in seeing them naked, you need to break that shit down. You might start by seeking friendships with other femmes (if you don’t already have any) and un-learning the cultural conditioning that femininity is weak or embarrassing or whatever other shit dudes try to distance themselves from by buying “manly” black loofahs. You can also, while you’re at it work toward dismantling the idea, still sadly prevalent in many queer spaces, that all the femmes are in competition for all the butches and vice versa — -an idea that precludes real, deep community connections by casting everyone as either a rival or a sex object. So gross, yet so easy to stumble into.

But maybe when you examine your deepest secret heart of hearts, you’ll find that while you respect and value femininity in all its forms, masculine women are what makes your junk truly sing. And that’s fine! People have types, and yours might always be girls with short hair and men’s jeans. Just make sure that you’re relating to your dates as individuals, not Hot Butch Archetypes, and don’t pressure anyone to perform gender in a way they’re uncomfortable with. You’re gonna be fine.

So I know that bi-invisibility is a thing. It is a thing that caused me several years of continued confusion and anguish because my sexuality didn’t seem to fit either binary before I finally had an epiphany on a hilltop (not a metaphor).

Because I felt confused and like I didn’t fit in either category for so long, I feel strongly and overwhelmingly positively about identifying as Bisexual. And I realize that makes a lot of people uncomfortable. That’s fine, actually. People are ignorant; people are rude; people are uncomfortable and determined to make that my problem. But can I make my family stop being those people?

I have an extremely loving and boisterous family. Most of them responded with something along the lines of, “Oh, okay, great! You kinda scared me what how serious you looked when you said that. Are you saying this because we’re about to meet someone special?” But some of my closest family members have responded by challenging my right to identify as Bisexual.

I have tried to lovingly explain the importance of the label to me personally, the problem of bi-invisibility, and the fact that it is not their decision with decreasing patience. It ranges from suggestions of alternative labels to conversations that seem designed to make me say, “Never mind, I guess it was all in my head in the whole time!”

I feel like I have done my due diligence in explaining things to them. Now I just want them to cut this shit out. Any chance there is a tried and true, loving but firm way to tell them to shut the fuck up? In a way that doesn’t lead to them getting defensive and retconning their initial freak-outs?

Oh buttercup, if there were a tried-and-true, loving-but-firm way to get disrespectful family members to shut the fuck up about things that are none of their business and I knew what it was, I would be selling it for hundreds of dollars a pop, not writing it in an advice column that people can read for free. And I would be a millionaire. And I would be responsible and pay off all my student loans first, but then I would buy myself a big-ass Harley and drive it around the country buying unreasonably extravagant souvenirs for all my family and friends. And then I’d get a house, not a huge crazy house but just a comfy one with a little extra space so I don’t have to panic about where I’m going to put every new book that I buy.

But, given the number of books piled on the floor next to my bed, we can only surmise that such a technique does not yet exist — -or if it does, I haven’t heard about it yet. There is no foolproof way to make other people respect your choices, your identity, or your boundaries. Some people sadly, are just going to act like dicks no matter what you do. If you’ve patiently explained your orientation over and over and they’re still challenging you about it, they probably have a case of chronic dickitude. Though some people do go into spontaneous remission, in most cases it is incurable.

The only thing you can control is how you behave toward people who are dicks to you. You can choose to tolerate it for the sake of familial harmony, and just cheerfully steer the conversation in a different direction whenever your orientation comes up. In action, this looks something like: “Oh, I don’t want to talk about that right now. I’m more interested in hearing about Aunt Kelly’s vacation in Hawaii! Did you take any pictures?” You can shut it down hard — -absolutely refuse to discuss it further, and get up and walk out if they keep pushing it. In action, this looks like “I am not going to discuss this with you anymore. Change the subject or I’m out of here and I’m taking this entire pan of casserole with me.” Or you can cut off contact with them entirely until and unless they get their dickitude symptoms under control. All these tactics have pros and cons; you just have to decide what’s best for you. Good luck!

Previously: “Too Many” Straight Friends, Hiding Your Sex Tools, and Life in the Queer Lane

Lindsay King-Miller is also on Twitter, and you can peruse the AAQC archive here. Do you have a question for her?