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Boyfriend Has Lots of Baggage

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My best friend (let’s call her jane) dated (lets say bob) Bob for over a year and had a miscarrige with their baby, they broke up and now she is with his younger sibiling. I am with BOB and Jane has been my best friend since kindergarten. But theirs no bad blood their, but the thing is Bob cheated on jane and has cheated on almost every girlfriend he has ever had. He cheated on me by kissing his ex, then messaging a girl on facebook, and then he invited a girl over to his house. (they apperantly did nothing) The thing is i wanted to prevent all this cheating. So the day we got together, i had a threesome with him and another friend. I was hoping if i showed him he could do other girls with me, he wouldnt do it behind my back. We’ve had two threesomes and the girl from the second threesome was the girl who was at his house. All of this was a couple of months ago. We have only been dating since July 2011. I constantly worry hes cheating, i’ve wanted so badly to invest in keyloggers to see if hes cheating on facebook but i know it shouldnt have to be like that. He’s so sweet and i have never had a boyfriend who i have felt so loving on. We have not spent a night apart, but he is a high school dropout and i go to school and college. He has no job either. I love him more than anything though regardless…What should i do? Is it time to give up or do i keep working?

Boyfriend Has Lots of Baggage

Answered by on -


I can’t tell you what to do. I think you’re telling yourself but you’re not listening. You are with a guy who has a long history of cheating. He has given you reason to think he hasn’t really changed. You don’t trust him. On top of that, he doesn’t look like a very substantial person. He isn’t in school. He isn’t working. Meanwhile, you are engaging in threesomes in order to try to inoculate him from cheating? That makes no sense. Basically that behavior gives him a message that it’s okay with you for him to connect intimately with other women as long as you’re there too. Is that really what you want to be doing?

Why aren’t you looking for someone who knows how to be faithful without manipulations on your part? Why do you think you’re in love with someone you can’t trust and who is going nowhere? I don’t get it. I don’t think you do either.

I wish you well.
Dr. Marie

Boyfriend Has Lots of Baggage

Therapists live, online right now, from BetterHelp:

Dr. Marie Hartwell-Walker

Dr. Marie is licensed as both a psychologist and marriage and family counselor. She specializes in couples and family therapy and parent education. Follow her on Facebook or Twitter.

APA Reference
Hartwell-Walker, D. (2018). Boyfriend Has Lots of Baggage. Psych Central. Retrieved on November 26, 2020, from
Scientifically Reviewed
Last updated: 8 May 2018 (Originally: 12 Mar 2012)
Last reviewed: By a member of our scientific advisory board on 8 May 2018
Published on Psych All rights reserved.