99 Problems, Romantic Fuck-Ups, And Comfortable Shoes

by Lindsay King-Miller


I don’t identify as anything right now, sexually. I’ve exclusively dated boys and men throughout my life so far (I’m 27) — I had a girl crush when I was 18 that didn’t go anywhere, even in my head, drunken sex with a girlfriend when I was 19 that was just terrible for both of us, and have been occasionally superficially attracted to other women since then. VERY occasionally — like, maybe three times in the last five years. I always had a boyfriend, and it never even crossed my mind to do something about that attraction (beyond the oft-lamented ‘make out with your girl friends at the bar’ behaviour of my early drinking age).

I’m single again. I recently started exploring kink, and have found a community where I can feel more myself than ever before. I identified myself as “heteroflexible”, cause sure, maybe I’d sleep with a girl if I was attracted enough, but it was really abstract and I still pictured my future having a long-term male partner in it.

I met a girl.

It’s complicated. She’s bisexual and poly, and her relationship with her boyfriend is on the rocks right now, so she isn’t introducing new relationships until that conflict is sorted one way or the other. In fact, we met just before that happened — I went on a date with the two of them and was attracted to both, but she and I are like wildfire together. She’s into me. She’s said so in no uncertain terms — but she has a primary relationship (presumably, if it works out) and we’re just going to have a flirty friendship with a lot of sexual tension for a while while we get to know each other. Which I like!

It has left me kind of…in a shambles. When she hugs me goodbye and her hands run down my sides, I shudder through my whole body. We’ve had moments where we’re both fighting not to kiss each other and they’re electric. We talk constantly. She’s hilarious and tough and beautiful.

So…this is going on in my life. It’s exciting. I don’t know what I “am.” I don’t feel like I’m bisexual — not because of the stigma of the term, but because I feel like I don’t deserve that label. I haven’t had to deal with the consequences of being not-straight in our modern society, as open-minded as it can be sometimes. I haven’t been on a proper date with a girl, let alone had a functioning relationship with one, and I haven’t had sober sex with only a girl (just some, ahem, threesome-type things). I feel like calling myself bisexual or queer steals a label from people who have to fight for their self expression when I’ve done nothing of the sort. In fact, I’m terrified that I actually want to date this girl — I don’t just want to get her naked. I feel like that’s so weak compared to the strong queer women I know who end up framing so much of their personal lives as activism because it still is a big deal sometimes to kiss your girlfriend goodbye in front of her workplace, or hold hands at school.

So all of that sounds like just whining probably. I’m struggling with my identity right now — I feel kind of like a straight girl imposter sometimes, but the feelings are real. I’m not bi, straight, queer, or heteroflexible, I’m just me! But the kicker is, I thought maybe it would help legitimize my feelings to myself to tell my friends this is happening. And it’s like they want to give me a fucking medal! Like they’re patting themselves on the back for now having another (or their first, in some cases) ‘queer’ friend, like it’s so cool of me to be into a girl in a serious way. I just want to be able to talk about her like I would talk about any guy I crushed on. Not have it turn into some weird (and oddly patronizing) conversation about my ‘lady friend’ in cooing voices. UGH. And I feel guilty admitting to my bisexual friends that the thought of dating a girl for real is so scary.

This is an example of what I’ve just decided I’m going to call a “99 Problems” letter. These are the ones where you’re not so much presenting me with a clear-cut dilemma and asking which of several options you should pursue; you’re more like dumping a big bag of thoughts and emotions on me and going HOW WHAT WHY. Which, to be clear, I love, because life is super complicated and clear-cut dilemmas are very rare and it’s good to be able to slow down and look at a complex situation and tease out all the factors that are jumbled up in there and address them one by one.

OKAY, so there are like eight things going on here and I’m gonna tackle them in no particular order:

1. You don’t need a label to like someone. You don’t need a label to date someone. If you don’t feel you’ve found a word that accurately describes your sexual and/or romantic orientation, that’s totally fine and you can feel free to not use one, or make up a new one, or whatever sounds best to you! It’s not like there’s one perfect word soulmate out there for everyone and your job is to track it down and hang it on your wall. Your job is just to go after your truth with everything you’ve got. If you want to call that a word, go for it. If not, that’s cool too.

2. But if you do want a word, or if not having one is giving you an existential crisis (as is sometimes the case), please feel free to help yourself to “bisexual” or “queer”! You like dudes and at least one lady. You want to sex up dudes and at least one lady. Welcome to the club, kiddo: you’re not straight.

3. I know you think you haven’t earned your non-straight orientation because you’ve never faced discrimination, but here’s the thing: you do not have to have suffered to be queer. Wait, can I say that again, much louder? YOU DO NOT HAVE TO HAVE SUFFERED TO BE QUEER. We don’t have hazing rituals. Yes, most of us have experienced discrimination at some point in our lives — and I’m sorry to say that you probably will too, if you date this girl/any girl in a publicly visible way — but that’s not what makes us queer. I worry that focusing on suffering as the arbiter of queer experience leads us to downplay what’s great about our lives and may even scare some people (maybe you!) out of coming out. If you are a lady and you want to date a lady, you’ve already passed the initiation.

4. Hey straight people, if you really are cool about The Gays, can you just like…not make a big thing about us coming out? Can you please at least try? If you’re constantly talking about how queer couples are “soooooo cuuuuuute” in a tone you otherwise reserve for videos of baby animals becoming friends, it makes us suspect you’re trying to overcompensate for some unsavory stuff in the back of your mind. If you are, don’t make that our problem.

5. In case your friends didn’t read that last bit, you’ll need to decide whether you’re close enough to them that you can say “I feel like you’re singling me out for being queer, can you please just act the same way you would if I was crushing on a guy?” If you think this will make them super-defensive or otherwise cause more trouble than it’s worth, I can’t offer you a better solution than just sort of subtly cutting down on the amount of time you spend with them — and also, of course, working on making more friends in and adjacent to the queer community, who won’t get all weird on you.

6. I totally get being scared before dating a girl for the first time! Being publicly visible as queer is intimidating, but really, most of the time it will be fine. I can’t a hundred percent guarantee that no one will be a dick to you, but probably that’s all that will happen — a little rudeness, some awkward social situations. It will be more than worth it to be with someone who makes you feel the way this girl does.

7. If you’re less scared because other people will know that you’re queer and more scared because OMG HOW DO I DATE A GIRL, let me reassure you: there are no lady-dating secrets that everyone but you has already mastered. We all pretty much start from scratch every time we get with a new person. Just be as kind and as honest as possible. Things will either work out or they won’t, but as long as you’re not egregiously unfaithful or abusive, it’s mostly out of your hands. Sometimes the kind of intense attraction you’re talking about grows into real long-term love. Sometimes it doesn’t. All you can do is wait and see.

8. But, um…this relationship is…not going to work out. I mean, you know that, right? I’m not saying polyamorous relationships can’t work, but I am saying that someone who may or may not be in the process of breaking up with her long-term partner does not have the emotional energy to pursue a new romance. Please do yourself this favor: don’t wait around for her to get back to you. If you do, you’ll look around one day and realize you’re miserable, your self-esteem has dried up like an undernourished house plant, and you’ve passed up on lots of cool people you could have dated while this girl tended to her other loves. If she’s not going to put the time into dating you now, don’t wait and see when she finds the time, because the odds are good she never will. You say she’s left you in a shambles; that is not what it feels like to be on the brink of a lasting, stable love. Go make out with someone who’s emotionally available.

So, I’ve identified as bisexual for a few years, because I feel about the same level of attraction to men and women’s bodies and a lot of my fantasies are gender-interchangeable, and am out to my parents and a few friends. When I was a teenager I was kind of shy and repressed and too uncomfortable with myself/around others to really crush on anyone for a long time. It was actually pretty hard to build up my confidence in this respect because nobody was interested in going out with me at all while I was school. Now I am a lot more confident in many ways, and also now I get crushes on guys all the time and it’s something I associate as a fun, good feeling. Having said that, my occasional experiences of casual sex with guys have ranged from mediocre to pretty bad, and made me think wistfully about sex which could be about women making women feel good.

With girls, though, I much more rarely feel that fun, exciting crush feeling where you want to be closer to someone, and I can’t figure out whether this stems from a belief that they would never be into me, or internalized sexism, or if I am more romantically orientated towards guys. I wish I could stop watching myself like a hawk, be properly out and just give feelings a chance to develop, but the thing is that I spent almost all of last year studying in Russia, where I spent the whole time passing as straight, encountered a lot of homophobic views from my Russian friends, and even my international friends who I hung out with were all straight, so I had no chance to do this.

SO what I’m getting to is that I have an internship in Berlin this summer and living there will be a big change, and I would really like to start feeling more comfortable with my queerness. But I feel really shy and nervous about this and have no idea how to go about it on my own! But also, saying to a friend “I’m bi and I want you to come to a gay bar with me so I can meet girls” seems like an unbearably vulnerable thing to do because I feel this huge mess of uncertainty/doubt/self-pressure about my sexuality. How do I overcome these internalized barriers? I will probably go with the ‘get drunk and kiss someone in a club’ route but would welcome some encouragement!

For what it’s worth, I seldom got crushes on women when I was younger (although the few I did have were long-lasting and all-consuming). I was attracted to people of all genders, but always more into guys — until the first time I slept with a woman. When that happened, and it was every bit as awesome as you’re imagining lady-sex to be, my romantic compass suddenly swung girlward. You may find, if you shake off your inhibitions and hook up with a woman, that something similar happens to you. Or you may find that you enjoy sex with women but your primary romantic attraction is always toward dudes. Either of those things or dozens of other possibilities are fine — I just think it’s worth remembering that your orientation may shift over time, and that doesn’t render either your current feelings or any earlier or later ones invalid.

Getting drunk and kissing someone in a club is a totally legitimate lifestyle choice (as long as you’re not too drunk to distinguish between enthusiastic consent and awkwardly trying to push you away). In general, I think you would benefit from acting on your feelings when you feel them instead of taking the time to analyze and compare and draw charts and otherwise get all up in your head, and if (a reasonable amount of) alcohol helps you accomplish that, what the hell, go for it.

Being in a more open environment where you can pursue your heart and/or genitals in whatever direction they lead you may also help in this area, but more than anything else, I think you need to get comfortable not knowing for sure. It seems like you really want answers for why you’re more attracted to some people than others (or attracted in different ways) and what that says about you and your orientation and your internalized sexism and fifteen other things, but really, a lot of the time it means nothing at all. It’s just the random vagaries of luck and happenstance and human chemistry. If you stop interrogating it so much, you might find it easier to just let it happen.

If you want to come out to your new friends in Berlin, you don’t need to make a huge deal about it. “I want to go out and try to meet some cute guys or girls, want to come with?” is fine as a starter. Try to relax about it as much as possible. Your orientation is not something you have to prove or defend to anyone. Just do what feels best and don’t worry too much about the consequences — a few romantic fuck-ups are a must for any well-rounded life.

I’m going to my first Pride this summer. Do you have any advice for me and my best friend?

I do! Here are some of the key things to keep in mind:

Wear comfortable shoes. You’ll be outside walking around, and those sexy platforms will start to feel a lot less sexy after a couple hours. Also, dress appropriately for the weather; don’t wear tights on a 95-degree day like I did last year because I thought they tied my outfit together. Those tights are adorable but sweating your ass off isn’t. Oh, and wear sunscreen.

Set a budget and stick to it. There will be lots of overpriced food, lots of overpriced booze, and lots of overpriced merchandise — go in knowing what you can realistically spend and don’t overextend your bank account. Advanced option: bring a water bottle and a bag of trail mix so you can stay hydrated and nourished without breaking the bank.

Assuming you can wear those shoes for hours of dancing and your ensemble won’t make you pass out from heat exhaustion, wear WHATEVER THE FUCK YOU WANT. There are no wrong answers. Formalwear, swimwear, superhero costumes — do you! Rainbows are great, of course, or you can rock the colors of whatever Pride Flag you relate to the most. It’s also fine to go casual if that makes you most comfortable.

Don’t pressure yourself to go to every single Pride-adjacent event. That way lies exhaustion and almost definitely overspending your budget. Check out a few bands, a drag show, an afterparty or two, but don’t become obsessed with showing up to every event all weekend (or, let’s be real, all month) long. Resist the FOMO, go home, and get a good night’s sleep.

Don’t drink too much. Retain the ability to stand up straight without assistance, recite your name without slurring, and give the cab driver coherent directions to your house. If you’re not sure about your tolerance, err on the side of drinking less. Your wallet, self-esteem, and digestive tract will thank you. Don’t forget that alcohol dehydrates you, especially if you’re drinking in the hot sun. Have some more water. And NEVER drink and drive.

Hookups happen, but don’t ditch your friends, especially if you’re their ride home. Your queer community is the people you’ll turn to when that hot chick doesn’t call you back — that is, if you haven’t already alienated them by blowing them off for a girl. And if you do go home with someone, have a check-in time at which you’ll call your bestie in the morning so she knows you’re OK.

It’s hard to make friends at Pride. Mostly people go to kick it with the queers they already know, and/or have drunken hookups. This is not the time you’ll form lasting emotional connections, I’m sorry to say — though you might find out about queer community resources that will eventually lead you to making lifelong friends. For now, though, if you want to meet new people who will remember your name in a week, your best bet is volunteering. Woman a beer booth or hand out pins; this will give you an actual opportunity to chat with people you don’t know and possibly befriend your fellow volunteers/organizers.

And finally, participate! This is your event as much as anyone else’s. Dance, drink, go to events you’d never normally attend, talk to people, have a good time. Manage your expectations — this will not be a religious pilgrimage, it will not change your life, it will be commercialized and sometimes awkward — but it can still be a great party, and you deserve to enjoy it. I’m excited for you! Have fun!

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