My boyfriend of 3 months has some odd behaviors that I can't quite put my finger on. He is in his 50's and I in my late 30's, he has two grown sons (and one is gay and accepted). He can be extremely concerned with appearance and expects the woman on his arm to match his style: he wears mascara , tanning products, tinted blemish concealer, high-end clothing and has more feminine emotions. He is also newly retired , divorced 6 months ago and spends money impulsively. He has had drug/alcohol issues most of his life although been in recovery for 10 years, and is a Vietnam Vet. Am I seeing a mid-life crisis or some unaddressed issues sexually?

My boyfriend of 3 months has some odd behaviors that I can't quite put my finger on. He is in his 50's and I in my late 30's, he has two grown sons (and one is gay and accepted). He can be extremely concerned with appearance and expects the woman on his arm to match his style: he wears mascara , tanning products, tinted blemish concealer, high-end clothing and has more feminine emotions. He is also newly retired , divorced 6 months ago and spends money impulsively. He has had drug/alcohol issues most of his life although been in recovery for 10 years, and is a Vietnam Vet. Am I seeing a mid-life crisis or some unaddressed issues sexually?

A midlife crissis might be buying a muscle car... what he has is personal issues.

The word to describe a straight man with effeminate ways is often 'foppish.' He could be straight, gay, bi, metro (whatever that really means), something of an open cross dresser, or he isn't sure, staying in the closet, or affecting the style just to throw people off. Bide your time and I'm sure all will be clear some day, if you are willing to wait.
I remember a man who let his hair grow long (neatly) and wore his wife's clothes. His wife had died, probably somewhat tragically and suddenly. Who knows what impels people?