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My best friend sexually propositioned me and I haven’t seen him since

Ask Roe: He casually suggested we sleep together; now I feel uncomfortable

Dear Roe,

I’m a woman and I am good friends with a man I’ve known since college. We were both single during Covid which I found very hard emotionally, as I felt like I needed extra support and I really missed physical affection – not just sex, but touching another person. I’m starting to look on dating apps but it hasn’t been going well so far.

During Covid, my friend and I talked a lot and were really there for each other emotionally. Recently I complained to him about trying to date, and he very casually suggested that we could start sleeping together, “no strings attached”. I checked, and he wasn’t joking. I said no, which he also took very casually, but I had to end the conversation because I felt so uncomfortable. I’ve avoided speaking to him since, even though he has tried to get in touch. How do I handle this?

You are allowed to feel awkward and uncomfortable when a friend asks you to have sex with them – and I think it would be helpful to explore the contours of your discomfort. I only have the information you’ve given me, but if he asked in a respectful way, didn’t pressure you, took your rejection cheerfully and has tried to make normal, friendly contact with you since, it seems like this is something your friendship can survive, if you want it to.


It may be that there were dynamics at play that heightened your discomfort. There may have been something about how he asked that felt dehumanising or objectifying or pressure-laden. This incident may have made you realise that he has said or done other sexually charged things that have made you uncomfortable in the past. Or it might simply be that because he startled you with this unwanted sexual proposition, you’re now uncomfortable and questioning his motives for your friendship.

These are all absolutely valid feelings – and again, not necessarily insurmountable challenges to your friendship, unless you decide they are.

You and your friend may simply view sex differently. He might think that sex between single friends can just be a fun experience and thought it was worth suggesting, but was more than happy to back off if it wasn’t your thing. Meanwhile, you might think bringing a sexual element into a platonic relationship feels objectifying and ruins the comfort and safety of it.

He could have absolutely been more careful before propositioning you, like asking about your opinion on friends-with-benefits scenarios generally to gauge your opinion, or asking if you ever had a crush on him. Sexual advances can ruin friendships, and he jumped headfirst into that risk. Maybe that’s what is upsetting to you: he was willing to make you uncomfortable and potentially lose you entirely, just for some casual sex.

(There’s also the possibility that this man has romantic feelings for you and was afraid to express them, so very awkwardly jumped to suggesting casual sex instead. Spoiler alert: this was a terrible plan.)

I suggest talking to him (over the phone, if that feels safer), and telling him that you are deeply uncomfortable that he propositioned you. He may genuinely apologise and explain his perspective which may be reassuring. He may belittle and dismiss your feelings, which will be a clear sign that he’s not actually a great friend. Or he may say all the right things and you may still feel uncomfortable. You get to feel however you like and you get to end friendships if you want to. But taking the opportunity to express your discomfort, perhaps gain some clarity, and set boundaries for your friendship if you want to move forward could be illuminating and empowering.