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General Dating Questions/Uncomfortable with my boyfriend's past

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My boyfriend and I have been together for seven months and we're really great together most of the time but I do have issues with jealousy.

I've never been jealous in any of my previous relationships, but my boyfriend's past and track record have me feel like I'm constantly playing defense. He's had sex with over 65 women and he's only 23. I find that disgusting actually. He's been in three long relationships totaling six years when he was supposed to be "off the market" and he started having sex when he was 14. He's cheated on every girlfriend he's ever had (before me), and the timelines always seem to change every time he talks about the past. Obviously he was adding women to his list during those six years he was supposed to be dating his exes.

The combo of his history of infidelity and his abnormally high number of past partners freaks me out. I'm always worried that one of his girl friends that he introduces me to is one of the girls on his list. It's happened, where he'll give a warm hug hello to a girl and and he brings up the fact that they've had sex after the fact, like it's not a big deal but it sucks to see him hugging these girls and knowing that there are 60-something more just like them out there somewhere. Most of them in my city. I know he's mine but to get to 65 he's clearly been less than discriminating in some of his choices and any girl could be a potential (or past) rival.

I know he's not cheating and he's been wonderful to me. Judging by our relationship alone, I'm happy with him, but I can't get these insecurities out of my head. How can I move past this? These issues are only with this man, and I've never been jealous before, but with him it feels like I'd be being naive to trust too easily. Do i just need to get over it?

I'm torn between self-preservation and giving him what I would want if our positions were reversed: the benefit of the doubt and a chance. If I leave because of his past, I could be writing him off unfairly (despite his track record, he could be really changed). If I stay, I'm opening myself up for a huge blow (that I would have seen coming) if he's just going to make the same mistakes with me.

Answer
I can't help but wonder why you'd start dating someone in the first place with a history like his. Speaking for myself I am 32 and have only had one sexual partner, and that was because my soulmate never came around. lol. If you are certain he hasn't cheated on you and has changed than yes I would let it go. But always keep an open-mind, and make sure he treats you with the up most respect at all times. I recommend the book, "intimate connections" by a Dr. Burns. It may help give you perspective on having a healthy outlook on interpersonal relationships to ensure that you give yourself enough credit.

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James

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First and foremost if you read ahead you'll find I have a word limit on questions I'll read. This site is for short simple questions and it should not be for writing essays. Please also note I am unfamilar with most cultures outside of United Stated, UK, and France. Please respect my rules. I don't like rejecting questions. I will be the first to admit that I don't know everything about dating, women/men, and interpersonal connections. However I have learned quite a bit vicariously from other people's experiences. Think of my advice as a second opinion. I would be happy to answer all questions related to relationships, dating, self-confidence, and self-image that I can. I have struggled with all of those things and probably know better than most how to deal with all of them.

I hope more than anything that my advice and opinions will help give people perspective in their lives, and hopefully make them feel better about themselves and their situations. I will attempt answering questions for anyone of any age group or nationality. However it would be particularly useful to know the age of all people involved. It does make a difference towards the advice I give. Also not terribly familar with arranged marriages and situations in which the family can dictate the details of the relationship.

My Rules:
1). I can't answer questions that ask if a girl or guy likes the other (very difficult to know remotely)
2). No questions that are More Than 250 Words. I understand that problems can be complex, but there is a real limit to how much I can read and fully understand. Particularly if English isn't the questioner's native language.
3). Only questions from Americans, Canadians, British, and cute French women.
4). No questions that ask the meaning behind if a person sets their FB status to single, coupled, or private or if they still have a dating profile undeleted somewhere. If you're cyber snooping you're likely the issue.

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I don't really have any specific experience in this area other than learning from other people's mistakes and a few of my own, and whatever I've learned as a psychology major.

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B.S. Psychology

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