Casual Dating, Girls’ Night Out, and Listening to Your Heart/Vagina

by A Queer Chick

I’m a gay lady who is starting to date? I guess? Like, actually date. I’m late-20s and am living in a medium-sized city. I’ve only ever had long-termish relationships (four of ‘em), and they all followed the friends > I like you > jk, I love you > full blown monogamous relationship pattern. BUT NOW, I’m in a new place, and I think I’m actively engaging in casual dating. So, I went on a couple really awesome dates with a great lady, and we banged and it was amazing. But we don’t chat during the week, and basically I don’t know much about her as a person (other than she’s fun and pretty). Now I’m talking to this other lady, and we’re gonna go on a date, and I’m excited! But what is proper protocol for informing either lady about the other one? How the eff do you casually date, like in general? I feel like such an idiot. BASICALLY TELL ME EXACTLY WHAT THE FUCK CASUAL DATING IS AND HOW DO YOU DATE MORE THAN ONE PERSON.

The Webster’s definition of casual dating says, “Haha, just kidding! There is no definition of casual dating. You’re on your own, sucka.”

Seriously, this is always going to be a challenging situation to navigate, and I’m sorry to say I cannot offer you a “get out of complications free” card. Dating casually can be super fun, like when you have two ladies who want to take you out, and the whole world is full of sexy possibilities. But it can also be hella complicated. Right now, you’ve got hot and cold running sex on tap, and that’s awesome. However, be aware that at some point in the future you’re likely to encounter drama. Begin constructing your Drama Levees now so that when the drama flooding begins you don’t… have to depend on… Drama FEMA? Yeah, that analogy kind of got away from me. Sorry.

The absolute best possible way to ward off future drama is through communication and honesty in the present. So, yes, you do need to tell the two girls you’re dating about each other. Otherwise I guarantee you that I, or some other advice columnist, will be receiving a letter about a month from now that goes: “I was banging this girl and it was going really great and then I asked her to be my girlfriend and she confessed that she was doing someone else on the side the whole time, THE HELL?”

Don’t make a big thing about it, but do be direct, with both of these ladies and any future conquests. Let them know that you are not looking for a serious relationship at this point in your life and be clear about the fact that you are dating other people. You don’t need to offer any more details than that unless the lady-friend of the hour asks for them (and you definitely don’t need to tell her how pretty/fun/smart/awesome at cunnilingus your other dates are). Hopefully she will then be like “That’s cool, I’m seeing other girls too. Do you want to make out now or grab some pizza first?”

There is always the possibility that she will not be down with dating someone who’s dating someone else and will remove herself from your rotation. But that’s fine, because it’s better to know up front if you two don’t want the same thing, and it frees you up to pursue ladies who are more compatible with you. As long as you’re honest and respectful (and always, always have safe sex), you should be able to keep the hurt feelings to a minimum.

Two of my bffs are lesbians, and whenever we have a girls’ night out they bring their respective girlfriends along. Do you think that’s fair? Seems like a weird loophole. Isn’t girls’ night for friends to hang out sans the people they’re fucking?

You are absolutely right. Girls’ night out (or guys’ night out) isn’t about the genders of the people involved, it’s about chilling with your friends in a totally platonic environment where you don’t have to watch them make googly eyes and call each other “sugar monkey.” Gay or straight, single or coupled, everyone needs some time to unwind. Plus, we all know that one of the main objectives of girls’ night out is to bitch about your dating life. How are you supposed to do that if your bestie won’t tear her lips away from her gf’s face long enough to hear your insanely awkward/hilarious morning after story?

The next time you’re making plans with one of your queer friends, tell her: “It’s not that I don’t like your lady — she’s a blast — but I would really love to hang out with you as you, not as one half of a couple. Can we keep this particular pub crawl / karaoke night / yoga class girlfriend-free, and make plans to have dinner with your significant other sometime next week?” If you don’t come across as jealous of or threatened by her relationship, she should be willing to leave her lover at home for an evening. (Also, don’t these girlfriends have friends of their own? Surely they can find something else entertaining to do while y’all are out and about.)

Of course, if she’s in the first six months or so of her relationship, it’s possible she’s experiencing the well-known honeymoon phase, and lesbian honeymoons are IN. TENSE. In this case, she may well refuse to be separated from her lady-friend even for a second, and there’s not much you can do about it except avoid making plans with her until the obnoxiousness subsides. If you do hang out with the happy couple, maybe carry a spray bottle or something, so you can squirt them every time the PDA goes overboard. I’ve never actually tried this on lesbians, but it works pretty well on cats.

I would like to get some pointers on meeting young, attractive, intelligent women who would nevertheless be crazy enough to want me. I am living in a cool new city. Since moving here, I’m still a chick magnet — it’s just that my polarity seems to have reversed itself, and I now repel instead of attracting.

A bit about me. I’m in my mid-twenties, nerdy, fat, but still probably good-looking enough? Because I get hit on all the freaking time. Just by cismen, though. Or poly women who already have primary partners. (I’m not sure how I feel about dating poly folks, but I am pretty sure I don’t want to be anything but a primary or an only.)

I understand that women don’t always want to be the ones doing the hitting-on, but I have no idea how to meet a girl at a bar or coffee shop, even if she smiles at me, bats her lashes or leans over and shows me her cleavage. (Believe it or not, this has happened!) So I decided to play to my strengths and made an online dating profile. I got all of two dates out of it, after messaging more than 100 women with specific, tailored questions.

So maybe I’m not cute enough, or not cute in the right way for girls, or . . . really, I have no clue. I’ve experimented with gender presentation in the past but am going through a pretty solidly femme phase. I’m also a creative type with a shitty pay-the-bills job, and I’m probably going to go to grad school for an MFA in a couple of years.

Any insights into how I can woo the queer chicks of my weird and lovely new town?

Okay, the phrase “women who would be crazy enough to want me” is giving me serious pause. For real? It sounds like you have a self-esteem situation that needs to be addressed. If you really believe that anyone who digs you is fundamentally flawed, you’re going to sabotage every relationship and potential relationship you have. I don’t know your life, and maybe you just wrote that as a joke, but maybe you didn’t, and maaaaaaaaybe that’s the reason you’re having trouble getting laid. If that is the case, then maybe what you need to do is think about getting yourself some counseling so that you can figure out why you feel that way and ultimately realize the essential truth of your own awesomeness. At which point you will have to hire a personal assistant to keep track of your Sex Calendar, because it will be coming at you faster than you know how to deal with.

But, assuming that a debilitating lack of self-esteem is not your issue, how do you start reeling in the ladies? I don’t know why your foray into online dating was unsuccessful — maybe your messages were overly self-deprecating; maybe your profile picture makes you look like a serial killer — but if random chicks are flashing you their cleavage in coffeeshops, you’re obviously attractive enough to get some. You just need to step up your game when it comes to meeting women in real life. This is rough, especially when you’ve just moved to town and don’t know a lot of people, but the more you put yourself in new situations the more opportunities you’ll have.

You said you’re considering an MFA program, so you’re obviously artistic — why not start hanging around galleries, open mics, or arthouse theaters? Give yourself a chance to meet women with similar interests so you’ll have a topic of conversation beyond “I like eating pussy too! What a coincidence!” Expand your horizons and your potential dating pool by signing up for a belly dance class or German conversation group. Invite some people from your shitty job over for potluck and board games, and tell them each to bring a friend.

Maybe part of the problem is that the women you meet aren’t sure you’re interested or that you even swing that way. Dating while queer, when you don’t have an established queer social group, can be mad stressful because you have to go through the whole dance of is-she-or-isn’t she before you even get into does-she-like-me-like-that. Why not hit up a dyke bar or other queer-themed social gathering, where just being there announces your vagina-centrism? If you were living in a tiny town in the middle of South Dakota I might accept “there’s no gay bar near me” as an excuse, but girl, you’re not. If the city I live in has a lesbian two-step class every other week, I guarantee you can find something nearby. Wear your shiniest rainbow jewelry, make sure your nails are trimmed and filed, and be prepared to start a conversation with a stranger. And there’s no shame in practicing a few opening lines in the mirror before leaving the house: “Oh my God, I love this song!” and “Oh my God, I hate this song” are both totally solid places to start.

I don’t expect you to diagnose me over the internet, but perhaps your experience and the stories of others might help me. I’m 24, bisexual, have slept with a dozen or so dudes, and made out with barely a handful of women. I never slept with any of the women who offered because it was a foreign country, I was nervous about being inexperienced, whatever. The thing is, I don’t actually like sex with dudes all that much! It’s fun the first few times, but once the initial tension has worn off, I can take or leave it. And I don’t ever get off without a vibrator, either with a partner or by myself. So in my current hetero relationship, which is a year old and Serious, I basically never initiate anything and don’t feel aroused by looking at or thinking of my boyfriend. We have been talking about marriage but things are seriously on the rocks because of my sexual apathy.

But I do get aroused by thinking about women, and I think a lot about how much I would like to someday go further than I’d dared before. The boyfriend knows I’m bisexual, but he says he would not be comfortable with a threesome or some sort of open relationship. I don’t think I’d even want that kind of arrangement anyway, since I don’t need to be sleeping with more than one person — I’ve just never experienced honest-to-god sexual desire in any of my hetero relationships, and I wonder if it’s not something wrong with me but rather that I’m with the wrong people. (Everything else in this and previous relationships has been fine, besides the sex, and I’m in love with the boyfriend.) Does this sound like a grass-is-always-greener situation to you, or actual latent gayness?

I feel the need to include a bunch of caveats with this one, like “I don’t actually know you, so” and “I’m just guessing, but” so that you don’t do something life-changing and then regret it and blame it on me. Because who the hell am I, really, to tell you what your heart/vagina truly wants? (In t’ai chi they talk a lot about the “heart/mind” as a single organ; I think I’m going to start doing the same with heart/vagina. It’s gonna be a thing.)

That being said, I don’t know you, and I’m just guessing, but I’m pretty sure you’re a great big homo. If it were just your lack of interest in sex with your boyfriend, I might surmise that you have a below-average sex drive (and if your libido is wildly divergent from your boyfriend’s, that in itself might eventually become reason enough to end the relationship). The fact that you only get off with a vibrator just means you need a vibrator to get off and will in all likelihood continue to mean that whether you’re dating a dude, a lady, or a toaster oven. But you don’t like sex with men, you’ve never liked sex with men, and you get boners thinking about ladies… welcome to the Portia de Rossi Fan Club, sweetheart.

But I kind of suspect that you knew that already. When you go within yourself and listen to the quiet voice of your heart/vagina, it always tells you the truth. What you really want to know is what are you going to do about it? Seeing as how you have this boyfriend?

You don’t have permission to screw around on your guy or have a threesome — and frankly, I kind of applaud him for that. Most of the time when guys “let” their girlfriends get it on with other ladies, it’s because they don’t actually see lesbian relationships as equally legitimate, and therefore aren’t at all afraid they will be dumped for a woman. (I shouldn’t knock this attitude completely, as it has contributed to my getting laid at least once, but I do find it pretty irritating.) Your dude is much more realistic about the whole situation. He’s obviously afraid to lose you, and realizes that’s a possibility if you kiss a girl and like it.

Unfortunately, he may end up losing you anyway. It sounds like, no matter how much you love him, you’re not satisfied with this relationship, and he’s not satisfied with your sexual disinterest. If he won’t give you a hall pass to fool around — and I’m not saying he should — you might just have to leave and get your exploring done elsewhere. Only your heart/vagina can tell you for sure.

Previously: Sexual Roleplay, Gaydar, and “OK, I’ll Bite.”

A Queer Chick is a queer chick who knows everything. Do you have a question for A Queer Chick?