10 questions you’re afraid to ask about your first lesbian relationship

I was straight until I wasn’t. And I think that’s the way it goes for a lot of women. You don’t know you’re interested in pursuing a woman for more than friendship until you know. But once you know, well, there’s a lot to discover. And I don’t mean that in a gross way.

When I started dating the first woman I ever dated (shout out to my wife), I was moderately terrified. I didn’t know how to be, what to say, what to touch and when to touch it. There are so many unspoken rules, it would take a cryptologist to decipher them. A lesbian cryptologist. Mainly because women are complicated, but in the best way. (Disclaimer: There really aren’t any rules if you’re dating the right person.)

So now that I’m married to a woman, and I’m still basically an expert at being terrible at dating, I’ve rounded up some of the questions I was afraid to ask when I first started dating a woman. I don’t necessarily know the right answers, if there even are right answers, but I know what worked for me. And if you or someone you know is a budding lesbian (or queer, bisexual, none of the above, or whatever term you prefer), these questions might be a good starting point.

1. How do I know if a woman is interested in me in a romantic way?

If she identifies as being a lesbian, and you feel like she’s being flirty with you, she’s probably interested. If she doesn’t identify as being a lesbian (or someone who is romantically attracted to women), and you feel a more-than-friends connection, you might still be right. Either way, the best thing to do is to just ask. Which of course can be super awk, but only if you let it. And side note, just because she’s a lesbian and being friendly, definitely doesn’t mean she’s automatically interested.

2. Who pays?

Generally speaking, whoever wants to. Often times, whoever does the asking will pay. It’s nice to be able to share the responsibility of paying for dates, that way neither of your bank accounts get hit too hard. Same goes for straight relationships too, I suppose. But this isn’t about them. This is about us right now.

3. Does one of us need to be more masculine?

No, no, no and no. I mean, if it happens, that’s totally fine. But if you’re both feminine, you can both be feminine. If you’re both masculine, you can both be masculine. Or if you flip flop between the two—also fine. There are no rules. Masculinity is subjective anyway.

4. What if I don’t know how to do sex with a woman?

Most first timers don’t. Women tend to be pretty patient and forgiving when it comes to sex. Let her know your apprehensions, and she’ll likely talk you through it. Or you can turn to the Internet for some tutorials, but those tend to be the opposite of realistic. My advice—trust yourself. You got this.

5. What if I hate sex with a woman?

You might, and that’s OK. Relationships aren’t only about sex. Once you fall in love, the sex thing tends to fall into place. But if it doesn’t, you may be with the wrong person (or gender), or maybe you just don’t like sex. If that’s the case, open communication will be key.

6. Do I need protection for girl-on-girl sex?

It’s always smart to be safe. Ask the right questions (aka, “Do you have any STDs?”). Maybe even get tested together before you have sex to be sure. You can also try using a dental dam, which is a thin square of latex used during oral sex to prevent STDs. It’s sort of like wearing a condom, but for women. But no one really uses them anymore. In fact, it may be hard to find a place that sells them. Which I suppose makes them vintage and cool again?

7. Do we need to move in together after three dates?


The old joke, “What does a lesbian bring on her third date? A U-Haul” is a joke for a reason. It’s an exaggeration of truth. Female relationships tend to move more quickly than straight relationships. But the answer is absolutely not. Move in together if and when you’re ready. So, after four dates. Just kidding.

8. Will I feel weird about holding hands with a woman in public?

Maybe? But hopefully not. The truth is, some women who are in healthy, long-term relationships still don’t feel 100 percent comfortable showing affection in public—especially if they’re in a place that isn’t very progressive—while other women care zero amounts what other people may or may not be thinking.

9. How do I tell my family? 

You know your family best. It’s never fun to live a lie, but if you’re still figuring this part of yourself out, there’s no rush to tell anyone. I told my family by just telling them. I made some sort of joke (because that’s what I do), and then probably said, “Haha, no but seriously.”

10. Will our periods sync?


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