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"Where do you get your hair cut? Have you tried X, he does mine" Or inivte him clothes shopping, and then make suggestions of things he could try on. I do think it is nice to try, but also to make sure he wants to be taken out. Also think about the dynamic, do you need someone who 3 years from now still has you as a social secretary? Maybe invite him to a few things and in 6 months how he is doing on his own. He be going out as he doesn't have the social skill to know how to say no! screw my wife Jersey City
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