Feel like we've veered way into a culture where from a courting standpoint, boys/ men are at a disadvantage from go. Particularly the "nice guys."
Things turn around once things get serious and everyone hits the corporate world, but damned if society hasn't pressured boys from an early age into an expectation of getting their dicks stepped on with high heels come dating time.
Ask them out like a gentleman, hand them some roses when you pick them up sit down and chat up their parents for 30-40 minutes to develop trust, take them to a nice dinner...
And then finger blast them by the lockers and let your buddies sniff the residue before you drop them back off before you tell everyone you fucked them.