I’m a 28 year old female and I have been in a “friends with benefits” relationship for 8 years with a guy that I went to high school with. We re-connected on Facebook and it started from there. Usually he would come over and we would hang out and talk for hours. I even sat by and watched him have two girlfriends during these eight years. While he was in these relationships, we were not having sex. But the crazy thing is that he never told me he was in a relationship… I had to find out from other people. Now I can’t get mad because of the whole “friends with benefits” title. Let’s fast forward to this year. He and I have become closer than we’ve ever been. He’s not dating anyone and neither am I. We recently started back having sex and now he tells me how pretty I am and how much he likes me. I have feelings for him and I want to tell him, but I feel like I shouldn’t invest anymore time into this because he has already said he doesn’t want a relationship. He said that he just wants to chill. Last week, he asked me if I wanted to go on a trip with him with his homies to Puerto Rico, but he text me today and told me he started talking to somebody, and she might want to come to. I don’t know what to do. Should I still be his friend or just move on to get myself out of this?
ShakeUp Letter 6/30: Friends With Benefits… I Think
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