Is there a way to differentiate, when saying "menaj", whether one is talking about a girlfriend or boyfriend. In my situation this guy is talking about "menaj mwen" and by his mannerism I think that it could be a "boyfriend" but I do not want to ask.

That's a tough situation, but unfortunately mennaj (menaj, mennay) translates both "boyfriend" and "girlfriend". Perhaps the next time when he talks about his "menaj", you could turn the conversation in English and he will have to SAY "boyfriend" or "girlfriend".  Or you could simply ask him for a picture of his "sweetheart:" :)

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