Most Helpful Guy
Current events and what u both are doing at the moment.
Most Helpful Girl
Well im a girl so I can't speak for guys but I've always felt that keeping things light and funny turn into a great night. Guys are so used to asking about you.. that theyre not even used to answering questions about themselves.
So I somehow try and ask a question they've never heard before. Something that's get them thinking and something that usually involves humor. Laughter is the biggest ice breaker so If you guys start laughing together.. things get mmore natural from there and talking becomes much less of a chore.
I once managed to ask this in a conversation.. I said if u could be a girl for one day what would you do. They answer and its usually funny.. I mean there's probably no answer to this that won't get a few giggles.. and he will likely ask you the same back. So answer with something even funnier. maybe even "dirty" it gets their imagination going and they let their walls down when they realize their not on a date with a prude. But don't go slutty.. just naturally open about sexual humor lol.