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How do I tell my friend-with-benefits that I want a proper relationship?

DEAR DEIDRE: I RECONNECTED with a guy with whom I had a “friends with benefits” arrangement years ago.

He wants the same again but this time I want a proper, exclusive relationship as well as the sex.

I know I’ll develop feelings for him if I keep seeing him

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I’m 33 and single. I’ve missed out on finding somebody since Covid and craved affection.

Recently I bumped into the man I’d been with in my early twenties. We went for a drink then had sex.

He’s now 35 and made it clear he’d like to see me again. But I’m worried I’ll fall into the trap of having the same casual fling.

I know I’ll develop feelings for him if I keep seeing him.

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He keeps going on about his ex, though. I think he still has feelings for her.

Should I tell him I want to develop a relationship with him?


DEIDRE SAYS: Yes, definitely. You have nothing to lose.

Explain to him casual flings are no longer your style and you are looking for something more long-lasting.

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If you can find the courage, ask him about this ex. If he is not over her, urge him to have some counselling.

And tell him that he knows where to find you if he wants to develop this relationship with you into something good.