Ask Darling D: My Boyfriend Has a Flirty Friendship

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Dear Darling D,

My boyfriend has a flirty friendship that makes me uncomfortable at times. It’s a girl from work and they’ve worked together for a while. He says they’re just friends, but I don’t like seeing how flirty she is with him and how he responds to it. I don’t think it’s worth ending the relationship over, but I don’t know what to do about it. Please help!


Jessika, Friends Shouldn’t Flirt

Dear Jessika,

I completely understand your discomfort seeing your partner flirt with someone else. I’ve been there too: I have it experienced it from your angle, I’ve been the S.O. that had a flirty friend, and I’m sure one time I was flirting with someone else’s guy. It’s definitely not easy, and uncomfortable.

There are many ways you can go with how to handle the situation, ranging from immature and passive aggressive to mature and adult. You choose what’s best for you! I’m going to stick with a mature and adult suggestion for you. Take it or leave it!

The best advice I can offer in this situation is to talk to your boyfriend directly. Unless you want to confront her, which is an option if you want to go that route, your boyfriend is the ‘monkey in the middle’ and the one you have a relationship with. Using that care and trust you already have with your boyfriend is probably the best chance you have of an honest conversation with a potential change in behavior. I gave similar advice to Ryann in this response and though your questions are very different, the recommendation for solution is the same: Ask, Share, Agree.

Some things I wonder off the top of my head: Does he notice her flirting with him, or is he oblivious thinking she is just being friendly? Does he like being flirted with, and if so why? Is he unhappy in your relationship, or does he thrive on getting attention from women? Is he social by nature and flirts back unintentionally? I don’t know your boyfriend and I don’t know the circumstances. But if I was his girlfriend, I’d want to ask some of those questions to try to understand where he’s at before telling him where I’m coming from.

Once you ask him some questions, directly discuss what you’re feeling. Have you been cheated on before? Does it make you feel insecure in your relationship? Do you feel disrespected? Everyone has different reasons for not wanting to see their significant other being flirted with by someone else and I don’t want to assume I know yours. But say your piece about how it makes you feel.

The last part of the convo is to come to an agreement of some kind. Are you looking for him to interact with her less? Do you want him to tell her to back off, or how you feel? The right answer is different for every couple. What is a realistic compromise that will make you feel comfortable? You don’t want to end the relationship over this flirty friendship, and you don’t want to be in a relationship causing you discomfort. If you can understand his side, and he can understand yours, a compromise to alleviate that discomfort and restore easy-breezy-ness in your relationship is bound to come up.

I’m rooting for you Jessika!

Darling D

Ask Darling D Flirty Friendship