Hi Yana,

I’ve had an above-average number of sexual partners (70+) and at least half have been one night stands. The pattern is: I start talking to someone on OKCupid, we arrange for a date, we have a few drinks, have sex.

Sometimes, it’s more mutual, and neither of us wants to see the other again. More often, I’ve enjoyed the sex (and they have too) but are not interested in meeting up again. Among those are situations where I’m interested in something casual but continuous. A few of them, I actually like a lot and am interested in something more than casual. However, overwhelmingly it seems that first date sex means no more dates. And I’m ghosted/soft rejected (“I had a fun time”).

There have been other situations where I’ve been sexual with someone on the second or third date, and it’s also happened. And that’s partly my dilemma. I tend to date a lot of women who identify as sex-positive, and though I don’t believe in a timetable for sex, it seems to happen sooner than later. And I don’t believe there’s anything wrong with that but I’m a bit tired of one night stands, despite my love of sex.

My hunch is that the fault lies with both parties in failure to communicate. Perhaps either one of us should take a moment before sexual activity to briefly discuss STIs and expectations. I have had only two such conversations in my life, both initiated by women. If I know it’s likely a one night stand, the interaction resolves better.

Still, why do you think first date sex seems to kill long-term potential for me? What do you think I can do to adjust my behavior for a different result? I feel it’s more complicated than simply delaying sexual gratitude.

—One and Done

 

Dear One and Done,

I think it’s great that you end your reflections about this pattern with wondering how you can adjust your own behavior for different results. A great way to wait a long time for change is to wait for other people to change while we kick back and stay the same. And this is especially true when it comes to sex and relationships.

I think initiating an up front conversation about sexual health and expectations for the interaction is a great idea. It sounds like having mistakenly high expectations for the date distresses you the most and adjusting them might make a big impact. Think of how much confusion you could clear up by simply asking someone if they’re interested in having sex or not, if they’re open to something other than a one-night stand, or if they want to be just friends, etc. Sure, it’s not “slick” but it certainly helps keep expectations and your date’s boundaries clear and intact.

Online dating apps like OKCupid make it a little easier to have these chats up front and could even be included somewhere in your profile that you’d like to talk expectations before you go on a date.

Of course, we can’t plan and account for everything before it happens. Sometimes we say we’re open to more if things go well and then they don’t go well — maybe the chemistry is off or the sex just didn’t click. And that’s okay. If you’re feeling brave, you could do some casual, possibly awkward research. Next time a date turns down an encore you could reassure her that you respect her boundaries and aren’t trying to change them and then ask her if there’s something you could’ve done differently.

You could attend some workshops about sex and relationships to check in with yourself and be sure that you’ve got your mechanics and techniques down or do some research online at home. And finally, you say you think this is more complicated than simply delaying sex until quite a few dates in but have you actually tried this approach? I might if I were you. Other parts of the pattern you’ve identified that you might want to subtract, examine, or alter are drinking during dates, meeting all dates on OKCupid, or saying yes to sex before you’ve discussed parameters.

Yana Tallon-Hicks is a relationship therapist, sex educator, and writer living in the Pioneer Valley. You can find her work and her professional contact information on her website, yanatallonhicks.com.