Readers’ dilemma: My friend flirts with all my boyfriends – and they love it

My best friend Carl and I have been mates for years. We met at uni and have been through all life’s big events together: coming out to family, first loves and the break-ups. He’s been a pal to me through everything, but the problem is he flirts with all my boyfriends – – there have been quite a few over the last few years. It’s always the same: as soon as I meet somebody new, Carl turns on the charm and crosses the line – flirting, being over-familiar, making jokes at my expense and generally loves to come across as better company than me. In most cases, the boyfriends have lapped it up – Carl is a good-looking guy and could have his pick of all the boys. I have just begun seeing a new boyfriend and it’s started up again – he and Carl are getting along like a house on fire and I’m the one feeling like a gooseberry. I want to have it out with Carl, but I don’t want to destroy my friendship.

Marcus, via e-mail

The Guyliner replies: First of all, you wouldn’t be doing anything wrong by pointing out to your friend just how out of order this behaviour is – if anything, Carl’s actions are already on their way to destroying the friendship. It sounds like Carl’s ego is getting the better of him. Like you say, he could have the pick of any of the guys, but the one he wants attention from is the one attached to you. Is it as simple as him being jealous that someone new is entering the frame? I don’t know. Carl could be using this as a way to boost his confidence – even the hottest guys can be a total mess inside, believe me.

You say two things that especially interest me. First, you mention there have been quite a few boyfriends over the years. Why aren’t these relationships working out? Just bad luck, perhaps? Or maybe Carl’s flirtatiousness is putting a strain on your relationships – the high turnover suggests your romances are all suffering the same issue. Is Carl that issue? You also say, for the most part, the boyfriends lap up the attention. Nice. This says to me that it’s not just Carl who needs dealing with; it’s the guys you’re picking. Any self-respecting guy in a new relationship would only have eyes for you; they shouldn’t be interested in the fluttering eyelashes of your so-called best mate.

A good start would be to socialise separately with Carl – in other words, leave lover boy at home. Maybe giving Carl a bit more one-to-one time will stop him behaving inappropriately with your boyfriend. You should definitely mention how you feel to him. Be calm and caring, but be firm – what he’s doing isn’t on.

Flirting might just be part of his DNA – maybe in the past he has sought approval from his own lovers and got little in return. Perhaps he is accustomed to using his looks to feel better about himself – who doesn’t like being found beautiful, after all?

Giving Carl more of your time and having a talk with him might make him see he doesn’t need to flirt to get attention. Otherwise, have a serious think about what means more to you: your best mate or finding lasting love.

Need some good old-fashioned advice on matters of love, life or relationships? Email me in total confidence on I can’t respond individually and your emails may be edited for on

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