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Tribune News Service
Lifestyle
Anna Pulley

Ask Anna: Why is casual sex sometimes fun and sometimes not?

Dear Anna,

My boyfriend of five years and I broke up around Thanksgiving. I spent most of the winter grieving and hibernating, but now that spring has sort of sprung and the world is opening up again, I’ve spent the last month “getting back out there.” I’m still not ready for a relationship, I don’t think, but I’m having fun exploring casual sex again after several years of monogamy. My question is: Why does casual sex sometimes feel awesome and empowering and other times I feel sad and dirty after? Is it me? My sex partners? Something else? — Hold Off On Knowing Unexpected Propositions

Dear HOOKUP,

Your vacillating moods post-sex could be from a variety of possible causes. You’re likely still grieving your previous relationship. After all, Thanksgiving wasn’t that long ago, especially after a five-year relationship. It could also be that casual sex just doesn’t do it for you — or not very often, at least. To that end, you might want to take a break from it and see how that impacts your moods. It could be that you prefer to have more of a connection with people that you sleep with, in order to establish trust and some knowledge of what you both like/want in bed. It could be that some of your recent sex partners lacked that trust, which might have made you feel “dirty” or “shameful” (even though there’s nothing dirty or shameful about casual sex). Or it could even be baggage from negative cultural and media messages about women who have sex when they want to. These descriptors tend to not involve words like “empowered” or “wonderful.” (Much to my chagrin.)

If any of those reasons resonate with you, then you might want to unpack them a little on your own — do some journaling, therapy-ing (if you have a therapist), or self-exploration on the topic and see if you unearth any insights.

My main advice to you, however, is to make sure that the sex you’re having (or about to have) is something you really, really want. Each and every time. Check in with yourself and your body constantly. (As an aside, if you’re drinking before these casual sex dates, that can make it harder to know what’s going on with your body and mind, so keep an eye on it and drink less or in moderation.)

A few ways to check in with yourself might involve: Taking a moment to pause and ask yourself how you’re feeling. If it’s anxious, fearful or suspicious, those are signs to pay attention to. A little anxiety is expected with a new sex encounter, but you should also be excited. Sex is fun! Not a performance review or a trip to the dentist (unless that’s your fetish).

You might also ask yourself if you trust this person to respect your boundaries. If the answer is no, then that’s another big sign to shut it down or scale back physically until you know the person better. You might also do a quick body scan. What’s going on in your body? Is your breathing shallow or relaxed? Is your chest tight? Are you tensing your muscles? Your jaw? Your shoulders?

If you’re on the fence about someone or a certain situation, then don’t do it. Even if in your mind it’s a maybe, that usually means it’s a no. Put the brakes on.

I know that’s extremely hard to do, especially in the moment. I’ve lost track of how many times I’ve “powered through” a lackluster or even outright awful sexual experience because I felt like I didn’t have a choice or I didn’t want to upset my partner(s). But that’s s—y and we shouldn’t be putting that on ourselves.

In every sexual encounter, your comfort, safety, and pleasure are THE MOST IMPORTANT THINGS. Let that be your guiding principle as you navigate these uncharted, sexy waters.

Good luck, HOOKUP.

PS: Last week a reader asked about terms for going down on someone on their period and the two most popular additions were “getting your red wings” and “bloodhound.” So there you have it. Eat, drink and be bloody merry!

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