Is It OK To Be Hooking Up With Multiple People At Once?

Q: How do you handle dating and sleeping with multiple people? I’ve met someone that I really hit it off with, but he wants to keep things very FWB and casual. I’m not opposed to this due to his work schedule and him traveling a lot, and we have a great time together.

I’m going on dates with other people with the intention of having a long-term relationship down the line. Should I cut it off with the FWB now before I sleep with the other guys I’m dating? Or since no one is asking anyone to be exclusive yet, am I doing anything wrong? — Sidney*

A: Hi, Sidney! You’re not doing anything wrong. In my opinion, the single most important thing you can do when dating is to be respectful and honest with the people you’re seeing, and you’re thinking about how best to do that in this scenario.

It sounds like you and your FWB have already taken the first step in talking about the parameters of your relationship. That’s a solid starting point, and it’s worth revisiting as you continue hanging out, to make sure no one ever feels taken advantage of. Healthy casual partnerships work because both people care about each other’s feelings.

I’m not sure what you and this guy have decided in terms of safer sex practices, but you probably need to have a convo explicitly about your expectations in this regard. People have different comfort levels with being in multiple sexual relationships at once — plenty of folks are totally fine with it, but it helps to be on the same page about protection methods, sexually transmitted infection testing, and how much you’ll share with one another.

We all need to be more upfront about sexual health, and that involves having conversations that might initially be uncomfortable.

While you don’t owe him exclusivity (like you said, no one is asking for that), I do think it’s worth telling your FWB that you still plan to date other people. If you’re looking for a long-term relationship, it’s not worth sacrificing that intention just to hook up with this guy when his work schedule allows for it. The best-case scenario here is that you get to keep dating people and living your life, and he can be a fun, sexy hang when he’s in town.

If you’re thinking “Sarah, this sounds great in theory, but I simply cannot have a conversation with someone I’m sleeping with about my sex life with other people,” I hear you. But if there’s one hill I will die on in this life, it’s that we all need to be more upfront in terms of sexual health, and that involves having conversations that might be initially uncomfortable but can ultimately be freeing. (My therapist would be so proud of me for saying this.)

How he reacts to this topic will be a good indicator of whether he’s someone you want to keep on the roster — and frankly, someone you can trust to keep your sexual health and well-being in mind, too. Down the road, if one of you meets someone else or starts feeling differently about your dynamic, you’ve set the groundwork for honesty. So when the time comes to move on for whatever reason, you’ll hopefully be no worse for the wear.

*Name has been changed.

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