I’m Zachary Zane, a sex writer and ethical manwhore (a fancy way of saying I sleep with a lot of people, and I’m very, very open about it). Over the years, I’ve had my fair share of sexual experiences, dating and sleeping with hundreds of people of all genders and orientations. In doing so, I’ve learned a thing or two about navigating issues in the bedroom (and a bunch of other places, TBH). I’m here to answer your most pressing sex questions with thorough, actionable advice that isn’t just “communicate with your partner,” because you know that already. Ask me anything—literally, anything—and I will gladly Sexplain It.
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Dear Sexplain It,
I just got out of a 15-year marriage where our sex lives were very much on autopilot. Now that I’m single and dating again, I’ve completely forgotten how to make the first move. I recently met a woman on Hinge, and after our first dinner date, there was this point where I should have kissed her when I said goodbye. I didn’t, and it was clearly awkward.
I have another date with this woman coming up, and I’d like to kiss her (and have sex with her at some point too). I feel so “out of the game.” The idea of merely kissing another woman is nerve-wracking. The idea of having sex? Even more nerve-wracking. Please advise.
Dear Newly Single,
First off, go easy on yourself. If you were extremely confident and had “game” on your first date after being married monogamously for 15 years, you wouldn’t be human. You’d be some sentient dating robot. You can and should feel nervous going out on dates, and you’re going to make some mistakes. There will be opportunities missed, faux pas said, and kisses unacted upon.
Plus, remember the good news: Clearly, you didn’t mess up that badly (or really, at all) because she agreed to go on a second date with you.
I’m not sure if you expressed this on your first date, but I would share that you are nervous. While the idea of being honest with your partner about your anxiety might sound scary, you’d be surprised how it can actually put you at ease. Say something along the lines of, “I want to be honest with you: It’s been a while since I’ve been on a date with anyone other than my ex-wife, so I’m feeling a little nervous-excited about this.”
Who knows? She might be a little anxious, too, and it would help for her to hear she’s not alone. Talking about your shared nervousness can be a form of intimacy that connects you two and makes you feel closer.
“The key is building intimacy before or during the date so that there’s less pressure on the all-important kiss.”
Now, onto your kissing conundrum. I know you’re also anxious about how to initiate sexual contact, and I think the key is building intimacy before or during the date so that there’s less pressure on the all-important kiss. When I showed your question to sexuality educator Francisco Ramirez, MPH, he suggested reconceptualizing how you think of “first moves.” This will not only help put less pressure on a single action, but it will also make the first kiss feel less abrupt.
“Don’t look at ‘the first move’ as just kissing someone,” Ramirez says. Instead, consider that all of your intimate actions and words can be part of how you initiate and express closeness with and desire for another person—from patting someone on the shoulder, to holding hands, to paying someone an authentic compliment. “You’ll see, then, that in many ways you’re probably already taking lots of different ‘first moves’ with each other, and hopefully feel less built-up pressure around a first kiss,” he says.
Ramirez also suggests being more upfront, or even just hinting at, your interests during other moments, not just when you’re about to part ways. “Communicating your interests (whether subtly or directly) before, during, or even after a date can help you get more comfortable with being bolder and sharing your desires,” he says. “Doing so will also help you gauge the other person’s interests and reactions as well, since we, of course, always want to make sure we’re paying attention to our partner’s signals as well.”
Ask yourself, “Is there something I could respectfully text this person today, right now, that feels a bit bolder and warms me up to the idea of being more direct about my interests?”
Maybe you text her, “So excited for dinner Saturday! If you’re down, it would be fun to go back to my place after.” If that feels too aggressive, you could instead say, “I’m really excited for our date Saturday. I’m looking forward to getting to know you better.”
Newly Single, you got this. You just need to embrace and own your nervousness. Not to be that person who says there are plenty of fish in the sea (because the sea is also filled with obscene amounts of trash), but she is the first woman you’ve been on a date with in 15 years. If things don’t work out, there will be other women, and with each woman you date, you’ll get a little bit more comfortable.
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