When do I bring up sex?

Friday | December 15, 2023

Love Letters Dating

When do I bring up sex?

I’m seeking letters about dating, marriage, divorce, and holiday issues. What’s on your mind about your relationship life? Submit an anonymous letter here or email
[email protected].

Also, former letter writers: how did it all work out? What happened after we heard from you? How has your problem evolved? Send an update to
[email protected] with “update” in the subject line, please (and remind me which letter was yours).

I’m in my 60s, recently happily divorced, and reentering the dating scene. I’m fairly fit, successful, emotionally stable, financially secure, and a pretty good conversationalist. But I haven’t dated in 40 years!

I’ve met some very nice, successful women on one app in particular. We chat a bit, then arrange to go for a hike or dinner. It all seems good and stable. But I have no idea how to broach the subject of sex with any of these women. (The dating site is a more mainstream site, not an overtly sex-positive site).

It’s not that sex is the only thing I’m looking for, but it will be an important part of any relationship going forward. How do I gauge interest? How soon is too soon to jump into the subject? I’m pretty deferential – or read that as passive, non-aggressive. I was that way even in my 20s. I don’t want to mess up a good thing by moving too quickly, but I don’t want to get 8 or 10 weeks in and find it will never happen. Also, I just don’t know how to start the conversation. Is it true that the majority of post-menopausal women are no longer interested in sex for the pleasure and fun of it? Thanks.

– Needing Guidance

Every woman/person is different. Post-menopausal people can be very interested in sex. There are lots of books and articles about this, and you can ask friends (or your doctor) all about it.

As for talking about it, get to the subject soon! No need to have eight weeks of warmup.

It’s not just a conversation about sex, but attraction. You can make it clear you’re interested in a physical relationship and see where that takes you.

Some opening lines for Date 1, 2, or 3, maybe after a Date 1 hug (if that’s where you are after one outing):

“I’m wondering if I can kiss you.”

“What if we kissed?”

“I’m really want to kiss you.”

“I want you to know I find you very attractive – and I hope I’m making that clear. What do you think about that?”

“Do you want to kiss me?”

(I should mention that I’m not very smooth. I tend to be blunt. Like, “I can’t tell if you want to kiss me. Please help me figure this out. I can’t tell what’s happening.” And by the way … that has led to a kiss.)

If the person isn’t into having a physical relationship with you, you can move on. Maybe keep them as a friend. Some people love a romantic relationship without sex, but you want some! Eight weeks is so much time. You’re an eligible bachelor, and yes, getting it on is part of figuring out if someone is right for you.

The world has changed (thank goodness), and you don’t have to act like some dude from the movies who effortlessly spins a woman in a circle and plants a kiss on her out of nowhere. In 2023, many people have realized that it’s nice to be asked questions. Some people who are very good at kissing (and more) are awkward during a first move. There’s space for that.

The most attractive thing can be honesty. Being told you’re kissable is nice. If you’re into someone and want to have sex with them, start by mentioning those first steps.

Then, if they’re into it, maybe ask them to come over and “watch a movie.” That’s still a thing.

– Meredith

Readers? When and how to you bring up this kind of interest? Any ideas or stories of your own?

Dating Divorce Sex 🖤

Featured Comment

“Why do you think you need to talk about it to someone you are dating? I would be very annoyed if a man I was dating asked me ‘when are we going to have sex’ I would want it just to happen, not have a whole conversation about it beforehand, buzz kill! If you like someone then Kiss them and see what happens from there, you will be able to tell by her reaction if she wants to go further than a kiss.”

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