Ask O’Leary: I’m a Gay Girl Dating a Straight Girl!

Hi Tim,

Loyal lesbian reader here. I know you usually deal with gay dudes and their problems, but I wonder if you could give me some perspective on this problem I have.

I went to a party recently that was mostly gay girls, but one of the girls there was straight (she’d come with her roommate). Straight Girl and I got to talking, and we hit it off so we agreed to meet for drinks the following night. We did, and she confessed she’d never been with a girl before but was always curious.

We hooked up that night, and there was so much push-and-pull from her, where she would stop in the middle of kissing me and say things like “This is so weird!” but then go back to kissing me. I’ve been down this road before with other “straight” girls, and it never ends well.

I have two questions: 1) Should I just back away now before I get hurt again? 2) Does this have any equivalent with guys?

Single Gay Female

Let’s deal with Question #2 first. Does it ever happen that bi-curious guys will go after an out gay man, but then feel conflicted about their feelings and return to the warm, familiar bosom of straightdom?

Yes, it happens. But with nothing even approaching the frequency that it occurs among women, according to my lesbian friends.

There’s an article on that suggests women may have evolved over time to be more open to bisexuality as a means of obtaining the security that there will always be another pair of hands for raising their children – if a dude isn’t around, another lady will do just fine. However, the evidence provided by psychologist Barry X. Kuhle, who posits this theory, seems pretty slight. Of course, I don’t write for a website with “science” in the URL, so what the hell do I know?

The conventional wisdom in the gay bars I troll, however, is that men are innately attracted to the pole and the hole with the same frequency as women, but society’s extraordinarily rigid confines of male sexuality prevent them from expressing this, and so they suppress it while their sisters are out there doin’ it for themselves.

So who’s right? Beats the hell out of me. But one thing’s for sure – this problem does seem to arise much more frequently for lesbians than for gay men.

Now to Question #1. Should you back away before you get hurt?

That’s a toughie, because there’s always the possibility that for the girl in question, this is a real moment for her where she realizes that there might be a lot more to her sexuality than what she had presumed, and it’s possible her mind is kind of blown right now. If that’s the case, she’s probably feeling a little vulnerable, so ditching her now seems kind of cruel.

On the other hand, you want to protect yourself, and not set yourself up to get hurt, either.

I think the best way to go about this is to communicate clearly what you’re both feeling every step of the way. It’s totally okay – and I encourage you – to let her know this isn’t your first time being “a first time” for a girl who previously identified as straight, and therefore there’s a little emotional baggage for you. Both of you should tread lightly, and be honest with each other at all times.

But again, what the hell do I know? I’m a gay dude who’s mostly dated other resolutely gay dudes. My friend Liz, a brilliant filmmaker based in LA who also happens to love the ladies, had this to say:

“This a prime example of some women’s fluid sexuality. Given that Straight Girl displayed hesitation during the hookup, it’s unlikely (though not impossible) for this to develop further. As SGF put it, ’It never ends well.’ My advice would be for SGF to back away, if only for self-protection. From what she wrote, it sounds like she has a history dating/hooking up with straight-identified girls who are curious but also a little flaky. If it never ends well, why start this one? There are easier ways to find and date women who like women (the Internet? Lesbian bars? The US Open?)

If SGF and this girl enjoy each others company, then cool, a new friendship … but I would have SGF ask herself if she could realistically be friends with someone she is attracted to, or if every hangout filled her with hope that she could change Straight Girl to Bi Girl. To reiterate my advice? Bye, Girl.”

Hey Tim!

I’d been seeing this guy – we’ll call him George – for about three months. We started our relationship very casually, but after a month we had “the talk,” and became exclusive. We both came into the relationship stating our expectations, which is total monogamy. Personally, I’m totally supportive of people who have open relationships. It’s just not for me.

Anyway, two weeks after we made it official, George (who gets a little crazy when he’s been drinking) accidentally slipped and slept with his ex after a night out with friends. He said his ex came over from out of the blue, that he wasn’t expecting it, and things just got carried away.

I forgave him, which was hard for me, but I worked through it. However, six weeks later, it happened again. This time it wasn’t with his ex but someone he knew from work. After that, I broke up with him for good. Believe it or not, that was really tough for me, because despite the cheating, he was probably the sweetest, most caring guy I’ve ever been with. Now, I’m having second thoughts. Did I do the right thing by breaking it off?

Worried in Wasington

Yes. You did the right thing.

You TOTALLY did the right thing.

Thankfully, your question was much less complex than the cheating issue we talked about last week. If you’re relationship is only official for two months, and in those two months he cheats on you twice, you can rest assured he’ll do so again.

Also, “his ex came over from out of the blue?”

Come on, WIW. How many times have your exes come over, uninvited, to your house without telling you?

I’m sure he seemed like a sweet guy when you two were together, but this dude sounds like a major dog. And what do we do with dogs? We get rid of them.

Wait, not real dogs, though! Keep thy wrath away from me, PETA!

Hey Tim,

What I love most about your column is your SciFi/fantasy nerdiness. I, too, like 98.3% of your readers love Doctor Who, and Buffy, and Firefly, and a good portion of what you talk about, but most of all, I love the classic fairytale prince/princess, good versus evil nonsense.

My question is whether or not you’ve ever seen The 10th Kingdom, and if you have, any thoughts? It’s one of those let’s-tie-all-the-fairytales-together gimmicks that came out back in 2000, so LOOONG before the others like Disney’s Enchanted, or Kingdom of Hearts, or Once Upon a Time. It has Ann-Margret as a 200 year old Cinderella; Camryn Manheim as an overweight Snow White; Dianne Wiest as the fiercest evil queen this side of Maleficent—–what more can a gay man ask for in a fairytale cast??!!

PLEASE tell me you’re a fan!

–Fairytale Freak

Now that is the sound of a passionate fan.

I confess I haven’t seen it, but I’ll definitely have to check it out. Thanks for the tip, FF!

Anyone out there seen it and feel as strongly as FF?


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