He’s hooked up with almost all of his friends

Chat at 1 p.m.

Dear Meredith,

I'm not too sure how to start this letter as I have never written to an advice column before, but basically I just want to know if I should be worried about my boyfriend's choice of friends. My boyfriend and I have been dating for four months. He's a photographer, so naturally he interacts with a lot of people. The profession also means he has a lot of female friends. In fact, all of his close friends are women. He has no friends who are guys.

To make matters worse, almost every single one of his friends has had a short relationship with him – a fling, a one-night stand, cuddled, made out with, or been generally more intimate with him than I would be with any of my friends.

I have brought my issues to him and told him that I don't like him hanging around these women because it makes me uncomfortable, but he continues to reassure me that it's fine and that I need to trust him. He knows he's flirty with other people and that I don't like it, but he doesn't see a reason to change. I don't want to break up with him because I love him dearly. I just want to know if I need to learn to trust him or if he needs to change some of his ways. Thank you in advance.

- possiblyoverprotective

Let's start with the part of the letter where you say you love him dearly. That's serious talk about someone you've only been dating for four months. You're still trying to figure out who he is and how he might fit into your life. A more accurate assessment might be: "I'm super into him and hope this works."

It's very possible – and probable – that your boyfriend's relationships with these women are all very platonic. You have good reason to believe him because he's been transparent with you about his history. But even if that's true, this relationship might not be a good fit. Not everyone can be super cool about a partner spending time with exes. That's why the four months thing is so important; you need to think about the life you might build with this man and whether you can be comfortable with his community.

My thought is: If you're asking someone to change fundamental parts of his personality this early in a relationship, it isn't a match. Maybe this will all make more sense to you – and feel safer to you – at six months. But if it doesn't, it's time to go.

– Meredith

Readers? Should the LW be asking the boyfriend to change?