I Had an Unexpected “Hook Up” That Didn’t Quite Deliver. What We Did Instead Was Just as Much of a Delight.

How to Do It This seems promising. Photo illustration by Slate. Photo by Zoran Jesic/Getty Images Plus. Sign up for the Slatest to get the most insightful analysis, criticism, and advice out there, delivered to your inbox daily. How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous! Dear How to Do It, I had a wonderful, unexpected “hook up” with an old friend of mine last night. It was unexpected because we’d been platonic friends for so long and never thought “hooking up” was ever a possibility for us. For context, I’m a 52-year-old male, and she’s 50. So we’re both older and insecure in our bodies. (Ah, aging!) When we got to the hotel room, she became shy and didn’t want to remove her clothes. I told her that’s fine—to be honest, I was wearing a compression tank top beneath my shirt (think: Spanx for men), and I wasn’t eager to reveal I was wearing such a garment, either. So we made out, fully clothed, and fell into a nice, comfortable sleep with one another. That’s as far as it went. It was actually still incredibly nice for me. (I’m totally over the moon about this encounter. It’s like the kind of super sweet encounter I’d have had as a teen!) The next morning I got two friendly texts from her, one referencing a joke I’d made the previous night. (“I’m still laughing about that,” she said.) And she wants to go out again this weekend. A great sign? If things go this well again, I’m wondering how I could—or if I should—address any body security issues we may have that would lead to a similar situation of keeping our clothes on. I’m not judgmental. And truth be told, just sleeping (as in literally sleeping) with a woman again did wonders for my self-esteem and mood. I hope she feels the same. I want her to feel comfortable too. But I’m extremely hesitant about my stupid mouth blurting out the wrong thing. Should I just keep it shut and let her lead? —Nervous But Happy Texas Dear Nervous But Happy, You have a long history of friendship with this woman, hooked up recently, slept in the same bed that night, and she followed up the next day asking to see you again soon. I think it’s safe to assume that your friendship is intact, and that she still feels comfortable enough with you to continue hanging out. Other than that, the next time you see each other is when you’ll be able to understand whether the nature of your relationship is shifting. Depending on how the two of you usually relate to each other, and where your comfort zone is regarding expressing yourself, anything from direct statements to comedy may be your personal best approach. Regardless, letting her know that you enjoyed making out with her, sleeping in the same bed with her, and had anxieties about revealing your man torso Spanx are all ways of giving your friend a manageably bite-sized sign that you had a good time and may be interested in more. Use what you know of her from your years of friendship to judge how blunt you need to be for her to understand what you’re sharing, and to weigh whether her response indicates that she has heard and comprehended you. Presuming you two head toward a private space again, if you haven’t brought up your feelings about your compression top, you can broach that subject in the room. Keep the focus on your own emotions around the topic, and be prepared for her to either commiserate or let you know that her shyness is about something else entirely. Feel it out. Because you’re describing yourself as having a “stupid mouth” that might blurt out “the wrong thing,” think about talking it over with a friend who is not mutually known to the friend in question, or rehearsing in front of the mirror. You clearly value the friendship the two of you have, and seem pretty hopeful about continuing down the path that the two of you ventured onto the night before you wrote this. There’s reason to be cautious about blowing it, and yet, the two of you have been friends for a considerable amount of time. She knows you. She knows your mannerisms, your way of speaking, and whatever amount of genuine awkwardness and self-criticism leads you to talk about yourself this way. It’s unlikely that knowledge and appreciation of you evaporated when the two of you kissed. Keep that in mind, remember to breathe, listen to what she’s saying to you, and I’m confident you’ll be able to, at the very least, achieve your aim of staying within her comfort zone. —Jessica More Advice From Slate I’m a cis male in a monogamous marriage and I’m on a mindless quest to scratch an itch that will never go away. I’d like to reduce my sex drive. Yes, I know this is a sex-positive column, but thinking about sex every 15 seconds is a pain. The constant distraction negatively affects everything; my career, family life, intellectual pursuits, friendships, etc. I also observe lots of men like myself blowing up their monogamous relationships, acting in an unwelcome manner toward women, engaging in risky sexual behaviors, and otherwise self-destructing… Never miss new Slate Advice columns Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays. Advice Sex