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About 8 years ago I hooked up with my boss. I had a crush on him since I started the job. About a year later we hooked up. A one time only thing because I found out he was in a relationship that I didn’t know about.
We recently found each other again and he asked about hooking up again and seeing where things go this time because he’s single. I don’t know what to do. My problem is that I’ve always liked him and I really don’t know what his real intentions are. Is he just after a piece of ass or is he being real about things going somewhere? I know I will get attached because I don’t just go have sex to have sex. Should I give it a chance or run?
Thanks for your question.
The red flag here is that he had sex with you while he was in a relationship. That’s really our only concern here. If he did that then who’s to say he’s really changed? But it’s possible. That would be up to you to figure out.
However, having said that, life is about taking risks. And if you really like this guy we don’t see why you can’t explore things. BUT…we wouldn’t start off by hooking up and having sex with him. That’s a bad idea. Very bad idea. If he really wants to see where things go, suggest a proper type of courtship. If he’s really into exploring a relationship with you he’ll be open to this suggestion. If he’s not, and he keeps pushing for sex and a FWB arrangement, then you’ll have your answer.
Hope this helps.
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