Phoebe's "stupid" brother

On having a kid : “i never had a Dad around and now i always will cause you know, it’ll be me

Asking Ross and Joey when they say he’s young and this is his time to sleep with lots of girls “Ok but isn’t sex better when its with one person you really really care about??”

When Phoebe tells him its for the best that his much older girlfriend broke up with him “yeah if the best is unbearable pain