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I even read up on personality traits on the internet and stuff that describe guys that are prone to cheat more than others...like background, or how charming he is, his personality.. etc etc...and when I read things that pertain to my boyfriend, I totally freak out. Are these accurate anyway??
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As a side note--no. Cosmo quizzes can't assess the status of your relationship.
Let's start from the beginning, you asked for brutal honesty, and that's my forte.
There are two seperate issues, with similar solutions. Issue #1 is your fear of infidelity, Issue #2 is the innapropriateness of your boy's comments.
Issue #1 is something you need to reconcile with yourself, not your partner--at least at this stage. Part of a relationship is being vulnerable--in fact, that's a huge part of it. When you relate to another person, you can't expect to form a deep bond unless you open yourself up as well--and the adhesive of the bond is trust. Your trust with your father, freud would probably have a fit, was broken with his infidelity, because he wasn't just unfaithful to your mother, but to you as well--shattering that image of what a male's role is. But you need to end the obsession with infidelity. I can't promise you that you're never going to be cheated on, but I can promise you that you're never going to find a rewarding attachment if you're going to be focused on how it could go wrong.
You need to determine whether you have the caliber of relationship that deserves your trust, and if you can trust your partner--you can work through a fear of infidelity.
Issue #2 is a legitimate one as well. After you're sure that your uncomfortableness stems from inappropriateness, and not from a lack of trust--don't be afraid to communicate. I'm telling you you're lucky that he even knows your friend's names, but tell him that you'd rather not talk about how good looking your friends are, and then give him a reason. That's all that's neccessary, a reason--practice it your head, post it here--because I think with that introspection will come the realization that this shouldn't bother you as much as you think it does, but that's not to say it's out of the question.
Just as an exercise, if you have time, fill in the following sentence. Be prepared to do it more than once, if you have more than one scruple.
I don't like it when he talks about my friends because...