I’m Sleeping With Someone Who’s Newly Single

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Hi Meredith,

I started sleeping with (and hanging out with) a friend of mine about a month ago. We’ve known each other for about two years – he was in a serious relationship until very recently.

So far things are going great. I really enjoy my time with him, and if he wasn’t so recently single I would be feeling very secure and confident in whatever is happening between us. I am trying to take each day as it comes, however, I feel like I am waiting for the shoe to drop. Like he will realize he just needs time by himself to be single and figure out …whatever.

I am not sure how guarded to be. I don’t want to be so open I get hurt, but I also do not want to stay closed to any possibility because I think he really is a great guy who I really enjoy spending time with. I know there is no way to never be hurt, but how can I protect myself?

– Open


“I know there is no way to never be hurt.”

That’s sort of the whole thing. If you try to anticipate all of the hazards and behave accordingly, you might wind up sabotaging the relationship.

The thing I’d focus on is that it’s only been one month, so I’m not sure how secure and confident you should feel at all. Yes, there’s a two-year friendship at the foundation of this, but the romantic part is new. You’re still figuring out what you like about him in this new role. Can you focus on that? What you like, as opposed to the ways those shoes could drop?

I very much believe that no matter how long friends-to-lovers know each other before coupling up, they hit a restart button when they begin their romance. You’re seeing each other in new, brighter light. Give it time to figure out what that means. (This could be scary for him, too, by the way. You’re not alone with the risk.)

Also know that some people get a good break between relationships. Others stay in relationships long past their expiration date and have processed the loss by the time it’s over. I can’t say whether this person is ready, self-aware, and fully content to be alone and choosing company for the right reasons, but … it’s possible. Or he could figure stuff out along the way.

Also, the two of you could end things for reasons that have nothing to do with his last relationship. (Sorry that isn’t very comforting, but it’s true.)

Let’s give this a few months. Try to breathe through the scary moments for now. Remember that even though you can’t prevent hurt and disappointment, you are brave and can bounce back.

– Meredith

Readers? How can this LW enjoy a new relationship without thinking of all the ways it could go wrong? Is it possible for something like this to work if one party is recently out of a long relationship?

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