Late Starts and the Umfriend

1. So, I’ve pretty much known that I’ve liked chicks from the time I was 13 on. However, because my spirituality conflicted with my sexuality, I never really acted on it. I went on a few dates with chicks in my late teens, got kicked out of my house for that and then stopped dating entirely. Here I am 32 years old now. I went through therapy hoping to “fix” my sexuality. It didn’t work. I went through a “de-gayification” program (for lack of a better phrase) that I ended up quitting because I felt like scum every “class.” I then did my own research on the Bible and all that stuff and found that it doesn’t conflict. Woot! So, now I’m entering the world of dating. I have no clue how to meet chicks, talk to them, date them… don’t even get me started on sex. How do I do this? I am this freakish anomaly that really hasn’t dated, is a virgin (yikes) and is really into Jesus. Am I doomed to be celibate (still) the rest of my life? Is there hope for me?

Oh, sweetheart! No, you’re not doomed to be celibate; yes, there is hope for you; and this wasn’t really a question you asked, but yes, you should definitely stop describing yourself as a “freakish anomaly.” Lots of folks get a late start at being gay, many of them for reasons very similar to yours: they’re afraid there’s something wrong with them, or they don’t want to deal with the judgment and discrimination, so they either try their damnedest to be straight or avoid dating altogether until it becomes clear that those choices are making them miserable. I promise, you’re far from the only person to be entering the queer dating scene for the first time post-30. Don’t be so hard on yourself about it, and when you do meet a lady you’re into, don’t present your inexperience as though it’s some huge embarrassing secret like uncontrollable flatulence or voting for McCain. There is nothing wrong with you, but if you come off like you think there is, chicks will sense it and you’ll have a much harder time getting them to take their pants off.

So what do you need to know about finding / picking up / getting down with ladies? A healthy social life is always a good place to start. The more people you’re meeting, the more likely one of them will be single, gay, and interested. Join a book club, take up yoga, go to an open mic night — whatever you’re interested in, find a way to be around other people who are interested in that thing. If your city has a decent queer scene, consider hitting up a lesbian dance night or something similar. We’ve talked about how it can be hard to find conversational ground beyond “You’re gay? What a coincidence, I’m gay!” at queer events; still, it’s kind of relaxing to know with 98 percent certainty that the woman you’re chatting up is not a straight chick thinking “Dammit, I knew these Converse were a bad idea.” 

When you’ve been out of the dating game for a long time, probably the scariest part of diving back in is the possibility of facing rejection. How do you steel yourself to the idea of putting your whole self out on the line and asking that cute girl for her number when you know her response might very well be, “Are you fucking kidding me?” Well, as anyone who has spent several years trying to make it in the lucrative field of poetry can tell you: oh, God, I’m never going to get a real job. No, wait, what I meant to say was: rejection gets easier to handle the more practice you have. The first time someone turns you down for dinner and a movie, you will probably feel like going home, weeping, watching your entire DVD box set of Firefly, and drinking a bottle of wine in a sitting. Go ahead and do that, it sounds like fun. But then the second time will be easier, and the third will be easier still, and eventually you’ll reach the point where a lady says “no thanks” and you’re like “Whatever, her loss.” (Just kidding, that never happens to anyone! But we all like to pretend that we’ll get there someday.)

The upside is that, among the rejections, you’ll also undoubtedly encounter some women who are totally into you, and want to get to know you better, possibly while naked! This is where shit is really going to get crazy. There is no way to prepare you for the first time a relationship becomes central to your life, then goes catastrophically wrong. (You may have already lived through this as a teenager, but I think given your decade-plus hiatus, we’re kind of starting over from the beginning, emotionally.) All I can tell you is: it’s going to happen, it’s going to hurt, and you’re going to live through it. Keep in mind that getting a late start on your romantic life does not mean you get to skip to the end any faster; you’re still going to have to get through the usual hopeless crushes, disastrous dates, and regrettable one-night stands before you find someone who really makes your heart/vagina sing.

As far as sex goes, again, don’t psych yourself out about being a virgin, and don’t approach it like you’re ashamed of your inexperience. It’s up to you whether to disclose to the women you date that you’ve never had sex before; I think it’s a good idea, especially if you’re feeling uncertain about what exactly to do and you want to move slowly, but it’s certainly not required. Either way, the best thing you can do for yourself as you prepare to plunge back in — a word choice I’ll almost certainly regret before the end of this sentence — is to masturbate a lot. And make sure to change it up! Use vibrators, the showerhead, or just your hand. Experiment to determine whether you like penetration, clitoral stimulation, or a combination. Fantasize wildly, and figure out what gets you wet.

All this solitaire serves a couple of purposes: first, it allows you to be clear with your future partners about what you’re into, which will make a huge difference in how satisfied you are with any sexual encounter. Second, the first time you’re faced with a vagina which is not your own, instead of thinking “Oh my God I have no idea what to do,” you can think “Well, I like some gentle back-and-forth rubbing at first, so I’ll start with that and see where it goes.” Be aware that what turns you on in the comfort of your own bathtub might not be exactly what you’re into when there’s an actual naked girl in the room, and be prepared to make adjustments on the fly based on what’s working for you or your partner. Things will probably be a little awkward at first, but that doesn’t have to be a mood-killer. Sometimes a shared giggle or a “well, THAT’s not as much fun as it looks in porn” can be a moment that brings you and your lady-friend closer together.

Oh, and the Jesus thing? I don’t think it’s going to get in your way at all. If you live in a big city, there is probably an explicitly gay-friendly church nearby — Google it — where you can meet awesome people who share your faith, and possibly make out with them. I went to one recently for my friend’s son’s baptism, and holy crap, there were a lot of cute butches there. I wish I’d known about this when I was single. (And still Christian, so I guess around age eleven.)

Congratulations on coming to terms with who you are and deciding to embrace yourself in all your queer awesomeness. Now, get out there and make some bad decisions, then come back here and tell us all about them!

2. Dear Queer Chick — I am going to make a long backstory very short: my parents divorced when I was two, and both of them remarried within two years. My dad and stepmom had four kids in the following 10 years, and while I love all my siblings, I am closest with my youngest sister. Dad and Stepmom (SM) got divorced about 15 years ago, and SM moved in with her “best friend.” I was in college by then, and knew pretty much right away that SM and her best friend were lovers, but it was never really discussed, nor did I care. (Enter comments here about hippie parental units who believed in free love, and loving the one you’re with and blah, blah, blah.) SM and her friend always maintained separate bedrooms, and never I never witnessed any PDA, but there was still a vibe, you know? I don’t know if it was just a show or not, since we live in a pretty small community, but whatever works for them, right?

Fast forward to my youngest sister going abroad for the last two years of her degree.  While she was gone, SM started introducing her friend as her life partner. When my sister came back to the States after graduation, she just about came unglued over this. All the rest of my siblings (including the ones from my Mom’s remarriage, because hey, we all grew up together) are totally cool with this situation except her. I don’t get it. She has gay and lesbian friends and is not a total asshole to them, but is the biggest jerk to her own mom, and to the person her mom has chosen to spend the rest of her life with! I have tried discussing this situation with her, but every time I do, it just pisses her off. It makes me sad, because now she just completely avoids her mom. What can I (or even should I) do to help fix this situation?

This is an awful situation that you’re in, and what’s even more awful — as I think you’ve already figured out — is that there’s really nothing you can do about it. Your sister’s relationship with her mom is complicated enough right now; if you get involved, there’s about a 1.6% chance you’ll make things better, versus an 89% chance you’ll offend or alienate your sister, which is the last thing she needs. I know it’s so painful to watch people you love hurt each other, but in this case, I have to advise you to stay out of it.

Usually I absolutely can’t be bothered to make excuses for people saying and doing homophobic shit. However, I can kind of see how your otherwise tolerant sister might have trouble coming to terms with her mother being gay. It sounds to me like she’s probably spent the last fifteen years in denial about her mom’s orientation and (perhaps) the role it played in her parents’ divorce; realizing belatedly that the woman her mom lives with is the woman she left your father for must be painful. Even if her mom’s current relationship is not what ended her marriage with your dad, the fact that she’s gay probably didn’t help. If your sister is struggling to come to terms with the newly revised history of her family — if she’s working through blaming her mother for her parents’ divorce — telling her to snap out of it will neither speed up the process nor improve your relationship with her.

Just be patient, and as supportive and loving as possible. If your sister insults your stepmom or her partner in your hearing, I think it’s fine to tell her that she’s being too harsh, but don’t push it to the point of a fight. All you can do is remind her — through your presence, not your words — of the loving, supportive family you both come from, and hope that will inspire her to decide her relationship with her mom is worth preserving.

3. So, as a straight, cis-gendered white girl, I want to be sensitive and thoughtful about how I refer to friends who would self-identify as queer. And maybe I’m bogged down in historical context, but I’m a little uneasy about describing someone as “queer.” It seems like a re-appropriation of a pejorative, and that as someone who is not a part of that community, it’s not appropriate for me to casually refer to a friend of mine as “queer”; I’m concerned that it could sound like Harry Crane on Mad Men. So, is this … a thing that I can say? Should I just consider the context, or is it never really okay?

I can’t really give you an across-the-board dispensation here, but I can tell you that I’ve never been offended by a straight person saying “queer.” It may just be the most successfully reclaimed formerly pejorative term in the entire English language. There’s even an entire field of academic study devoted to it. Sure, it’s still possible to use it as a slur, but pretty much anything can be an insult if it’s intended that way, right? (“Dude, that is SO pre-Cambrian.”)

I think you’re completely fine to use the word “queer,” especially when you’re talking to or about people who identify with it. A lot of folks really prefer it, in fact, and are much more comfortable comfortable being described as “queer” than “gay” or “LGBT” or what have you. Just be sensitive — if someone tells you they’re offended by it, don’t use it around them anymore. “But this queer chick on the Internet said it was okay!” is not a good excuse for anything, ever.

4. Perhaps this will sound terrible, but although I’m not sexually attracted to men, I’ve spent most of my life dating men because doing so is easy and safe. Basically, all of my long term relationships have been with men who I like, but do not love, with whom I enjoy snuggling, but not having sex.

In the last three or four months, a friendship with a beautiful lez lady has become something in between friends-with-benefits and romantic relationship, sans title. I enjoy every moment I spend with her, and I know she enjoys spending time with me as well. Basically, I want to date this girl. I want to do things which make her smile and introduce her as my girlfriend and use all of my available resources to make sure she never feels sad.

However, she thinks of me as straight, as does the rest of my social world. While we’ve had conversations about sexuality, she doesn’t take me seriously as bisexual, queer, whatever (I hate all of these words and I don’t know how to begin to apply one to myself). In conversation, she indicates that there is a big difference between me (and my kind) and her (and her kind) in a way that makes me feel a little bit like a joke. Not that she’s into binary essentialism or anything, but she’ll say things like, “I wish I had more gay friends. I mean, talking to you is great, but it’s not like talking to another lesbian.”

I don’t blame her for thinking this, I’m the one who has been lying to the world for about almost a decade, and she’s always known me as a girl who dates boys. I know she came out, loudly, very early in life, so I worry that she can’t relate to being 22 and still struggling with identification. Also, I get the idea that some girls have used her as a kind of “sexperiment” or drunk make-out-buddy without seriously breaking any hetero mores.

So, how can I convince her that I’m not just a tourist in gay-town? And, beyond that, how can I convince myself?

Hold up, this woman is having sex with you, right? I mean, I assume that’s what you meant by friends-with-benefits. You’re exchanging orgasms on a regular basis, but she still doesn’t consider you “gay enough”? I feel like the main problem you have here might just be that you’re banging a judgmental juicebox. Have you considered dumping her ass and finding a nicer girl to grind on?

Maybe that’s too harsh. Dating someone who’s closeted is no picnic, and I can understand why your umfriend (a useful term for those romantic-but-undefined relationships in your life, as in “This is Hannah. She’s my, um, friend”) might be hesitant to upgrade you to girlfriend status if you haven’t come out yet. Still — as she should well remember — coming out isn’t the easiest thing in the world either, and I wish she were offering you some emotional support, instead of writing you off as “one of those girls.”

Except … You have told her you’re not one of those girls, right? You’ve told her that you’re gay? Because you kind of avoided coming out and saying it in your letter, and instead described yourself “struggling with identification.” If you refuse to identify yourself as a member of Team Dyke, it makes sense that your paramour doesn’t see you that way either. But everything you say about your romantic and sexual predilections — not into dating boys, not into sexing boys, very into dating and sexing girls, particularly this girl — tells me that you’re gay with a capital I [HEART] VAGINA. You can call yourself “lesbian” or “queer” or whatever feels best to you, but the sooner you start admitting to yourself and the people in your life that you really dig chicks, the happier and healthier you will be.

I know it’s scary. I know it’s easier to continue dating boys, and telling yourself that you just don’t know who you are yet. But the thing is, I don’t think that’s true. You know who you are and what you want, and that big closet door is the only thing standing in your way.

So here’s what you do: you sit down with your umfriend, and you say “Listen, I know I’ve been hesitant to put a name on the way I feel about you, but that needs to stop. I’m crazy about you, and I want us to be together. And because you deserve a girlfriend who’s proud to be with you, I also want to come out of the closet and tell everyone that I’m gay. I hope you’ll be there to hold my hand when I do, because I am scared as hell right now.” Almost definitely, she responds with “Finally! I had just about given up on you!” and then you guys make out and everything’s great. (There’s a small but awful possibility that she will instead say “Wow, I’m flattered, but I’d really rather keep this casual,” in which case you go home, cry, and then start looking for a new lady — one who knows you’re gay from the start.) After that, you call up your friends, and any non-homophobic family members you’re lucky enough to possess, and you break the news: you’re gay, your “friend” is your girlfriend, you couldn’t be happier to get this off your chest, now who wants to go get a lot of mojitos?

Good luck, darlin’. This is going to be terrifying, but your life is going to become so much more awesome from here. I’m really excited for you.

Previously: Future In-Laws, Appealing Coworkers, and Lesbians With Interests (?!)

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

Photo by Anna Sedneva, via Shutterstock

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