When do I bring up sex?
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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 and 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 eight 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
A. Every woman/person is different. Post-menopausal people can be very interested in sex. As we learned from a recent letter writer, perimenopausal women can be quite interested, but maybe in new and different ways.
There are lots of books and articles about the wide range of people’s experiences. 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 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 kind of confused talk 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 strategy 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 like you too, maybe ask them to come over and “watch a movie.” That’s still a thing.
MEREDITH
READERS RESPOND:
Agree, start by asking on the first or second date if you can kiss her. Just ask for consent, don’t say any of the things Meredith suggested (lol sorry Meredith). I actually prefer a guy doesn’t try to kiss me on a first date but that’s my personal preference. Definitely do not start talking about sex, start with other more basic displays of attraction.
HELLOWORLD13
Why do you think post-menopausal women join dating sites? We have plenty of girlfriends to go to dinner with. Maybe wait till the second date, but listen for clues when chatting about past relationships and ask what they liked, disliked, and miss. Share your own stories. Use little physical touches. Grown people who like each other and enjoy sex should be able to express that.
RANDOMKINDNESS
The problem here is that you’re trying to think your way through a situation that is all about feelings. If you date someone a few times and start to have feelings for her, you can begin by telling her that. If she’s feeling the same way, you will naturally move into hand-holding, hugging, kissing, cuddling, and so on.
OUTOFORDER
Send relationship and dating questions to loveletters@globe.com. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.