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After a few months with your boo you should be able to hang out with his friends and even be introduced to his family.
If he hasn’t taken the initiative to bring you into his closest circle after a couple of months it may be a red flag because he doesn’t think of you as long-term girlfriend material or he is not planning to commit anytime soon.
If he doesn’t have a good relationship with his mom or his sisters and keeps holding grudges with his family after the years, chances are there is a deeper issue that hasn’t been resolved.
If he doesn’t respect your feelings and keeps on talking to his ex it is time to date somebody else.If you have to ask permission every time you want to go out with your friends, get a tattoo or take a painting class you may be dating a control freak.