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Comments:
Well not exactly asses, but he puts his arm on a girl's waist in a non-friendly way (I've never seen him do that to his sister, or his childhood unattractive female friends). Other girls sit in his lap, etc... The thing is, I'm not jealous at these girls (I like them a lot), I just don't like his behavior.
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We've been on this kind of schedule since day 1.
I am seeking a woman to spend time with..movies, dinner, dancing you know fun stuf.
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OP, when you are setting up your double date, how are you going to explain this to Ryan? Are you going to tell him this is a guy friend you have known since high school? If so, why didn't you bother to bring it up until now?
Also OP: if you cheated first(or even if you didn't) do you have any reason to believe your wife is aware of this?
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What's the rush of getting married anyway? What'll change for you that you NEED to get married within the next few years?
Things can change if you talk to him about it.
If he's teaching, and you're still only a student and teaching assistant, he may feel very awkward about socializing with you, even more than if you were just coworkers on an equal level.
So here is the situation...