Money

Girl: So I booked my cruise and my trip to Florida in the same week. People who aren't Jewish don't understand that going to Florida is not a luxury anymore.

http://www.overheardatmcgill.com/archives/2008/10/23/and-im-thinking-of-purchasing-new-rez/

Overheard by: second cup

Girl, pulling bills from strapless dress: Yeah! They's my stripper dollars.
Boy: Man! Sure wish I had titties!

Portland, Oregon

Guy holding another in headlock and punching him in the face, shouting across road to immensely fat girlfriend: Charl! Get that fucking taxi! We gotta get home or the babysitter'll want extra pay.

Leamington Spa
England

Overheard by: Bleep

Beggar #1: Spare change?
Beggar #2: Hey, I haven't seen you in a while.
Beggar #1: I just got back from California.

Boston, Massachusetts

Sorority girl #1: Yeah, I'd give him a blow job him if he gave me $100.
Sorority girl #2: So you'd prostitute yourself for low 3 figures?
Sorority girl #1: No! It's not like I would ever have sex with him, no matter how much he paid me! He's disgusting!

Indiana University Southeast

Patron #1: Yeah, but everything's different in Hawaii. You can't even buy land there unless you were born there.
Patron #2: Actually, you can.
Patron #1: Yeah, but all their laws are different than ours.
Patron #2: You know that Hawaii is a state, right?

Starbucks
California

Young suit to crying baby he's holding at arm's length: You were a terrible investment.
Young woman: Stop saying that!
Young suit: If he doesn't stop crying, I'm literally going to give him to the next person who is willing.
Young woman, taking the baby: He should be crying. You're an idiot!
Young suit: The sale has now become two for one.

Toys R Us
Bear, Delaware

Guy on crutches: I have nothing to offer a woman. It's like, “hey! I live at the homeless shelter, wanna go on a fucking date?”

Boston, Massachusetts

Overheard by: Libby

20-something boyfriend with arm around girlfriend: God, we've saved a fortune not buying condoms recently.
Girlfriend: Yeah, a few more years of this and a baby will have paid for itself!

Cork
Ireland

Dad: Okay kids, here's a penny for each of you! Throw it in the fountain and make a wish! Mark*, what did you wish for?
Mark*: A cupcake!
Dad: Okay! Joe*, what did you wish for?
Joe*: A garbage can!

Zoo
Philadelphia, Pennsylvania