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How to Deal with Jealousy/How to Make One Jealous/Can't get over my boyfriend's historic one night stand


Hi there,

I've been with my boyfriend for seven months. He's incredible, treats me better than I've ever been treated in a relationship before and I'm very much in love with him. I'm 33 and he's 37 so we obviously both have pasts. He's had several long term girlfriends, various short term relationships and several one night stands, and I've always found it hard not to feel jealous of these women but there's one in particular I can't stop obsessing about. He slept with a close friend's sister two months before he met me and although he tries to describe it as a 'dating' situation, it was definitely a one night stand as they both went drinking with a group of friends, slept together afterwards then didn't meet up again. Two things bother me. The first is that I have real trouble understanding why anyone would want or have a one night stand - I've only ever been intimate with people I've cared about and my boyfriend has been honest that he knew he wasn't compatible with this girl because she has a child and he's never wanted relationships with women with children, yet he still slept with her. The second thing is that this girl is now dating a close friend of my boyfriend and apparently her boyfriend knows about the one night stand, is absolutely fine with it and thinks the four of us should double date. It seems that of the four of us, I'm the only one who wouldn't like to
all meet for a drink but I just can't bear the thought of being in a room with someone I know my boyfriend had slept with. In addition we do have an agreement about not seeing exes as my boyfriend can be quite jealous and insecure too so I gave up going to the gym because my ex was an instructor there so I feel like its a double standard for him to want to meet an ex one night stand for a drink. But the fact that her boyfriend apparently doesn't care makes me wonder if there's something wrong with me because I can't bear the idea of seeing this girl. I just don't know how to stop obsessing about how my boyfriend could sleep with this girl and worrying that I'll have to meet her one day. Yesterday she wished my boyfriend a happy birthday on Facebook and I literally felt sick for hours afterwards but can't understand why when I know he loves me, she loves her new boyfriend and my boyfriend doesn't want a relationship with her. Please help me to get this in perspective!

Hello, Annie.   

Thanks for your important question.

First, I firmly believe that putting yourself in a guy's shoes is not the best way to understand men. Men and women are different and we experience many things, including sexuality differently. A one night stand can be a very exciting experience for a guy (and for some women) for a number of reasons - including due to pure sexual pleasure, the idea of attracting and being attracted to someone physically so quickly, and the idea of having a "James Bond" experience can also be appealing. You don't have to be able to understand it or feel it, if your attitude to this is completely different and you can't relate to it, but it would be important for you to appreciate the difference in nature between you and the guy/s.  

I can see why you won't want to be in the same room as that girl, at least for now. It shouldn't be very hard to skip a meeting and if avoiding her is what you need not to be rattled emotionally, you should stay away from her and skip those gatherings where she is present - at least for now. With time, you will likely get over this and being around her won't bother you. One thing that should help you is that she hasn't done anything bad to you. She had an experience with your boyfriend before you were in the picture, so you don't really have any reason to dislike her.   

Please also read these articles on overcoming jealousy that you might find useful to your own situation:



How to Deal with Jealousy/How to Make One Jealous

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I can answer questions regarding how to deal with one's own jealousy and how to deal with the jealosy of the partner / lover and how you can liberate yourself from this destructive emotion. Learn more about me and my work at


I overcome serious jealousy issues with conscious work and effort, and that was a very liberating experience. I also helped several people to abandon their jealous behavior and line of thinking.

M.A. in Philosophy

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