Legal Question in Discrimination Law in New York

Before you even get to the legality of it, let's start with some common sense. An 18-year-old man is not in the same place, emotionally and psychologically, as a 14-year-old girl, and may have expectations that may not comport with his underage girlfriend's mindset and comfort level, much less her maturity.

You don't say whose parents' permission you have (whether it's your parents or that of your male friend), but if it's your parents, I wonder what reasons they would have for allowing this. And if they are so in favor of this arrangement (which, quite frankly, I seriously doubt), why don't you ask them to seek to find out the legality of the situation. If they were so much in favor of this arrangement, I doubt they'd be sending their 14-year-old daughter to the internet to seek legal advice on underage dating.

So that you know, certain activities between you and your friend could get him in significant criminal trouble.

If you care about him, stay away. If you care about yourself, stay away.