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I'm not the type of boyfriend that will tell her who she can and can't hang around with. All that does is show my insecurity and if she thinks I disapprove of something she will do it behind my back no matter how small of an issue it is.
You revealed your insecurity by trying to babysit her with the hotel room. But I get your point.
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Moreso, it's her roommate and I'm not sure how I can keep the three of them from actually hanging out and I'm really interested in knowing how you prevent that from happening with your girlfriend, her friend, and her friends boyfriend since the two of them live together.
It's really easy. This is what I told my gf after her roommate and boyfriend tried a threesome:
"They've tried to have a threesome with you, your roommate straight up asked you a week ago, it's a known fact the boyfriend really likes you. Respect the relationship, and your ass is over here when he's over there. Or you go out and do something else".
The boyfriend is a free-loader who doesn't have his own place, so he's been flopping over there off and on for a year. I've come pretty close to having a "man talk" with the loser, but so far I have played it cool.
She respects it and agrees with it.
I know I can't really say much since I'm the one who actually had the threesome with her roommate, lol, but hey, that's life. If you don't want to respect the relationship, hit the fucking road, and I'll go fuck the hot bartender who's been all over my shit tomorrow night, and the blonde at the gym after that.