[flerchin]

I dunno man. Everyone else on your show says that dating is hard and it's extremely difficult to find someone who gets you. She seems to get you. You sound like you've already decided it's over, but I wish you'd give her another roll in the hay.

Whether the 2nd try also doesn't work, or if you don't attempt one, it still seems like you should follow Chemda's advice and put yourself through a little bit of discomfort to maximize her comfort during the breakup. From what I gather on your show, dating in NYC is much worse for women than for men*, and it won't cost you much to be one of the good ones.

*That Chris Laker is not single is astounding.