A "chipper" is your girlfriend's best MALE friend. He invites her to see the White Stripes and has long phone conversations with her. She tells you things like...I think he's gay..." just to make you feel comfortable with their relationship. And even though he gives her foot massages and buys her candles you're cool with it. Then you and your girl have a massive blowout and a few month's later...they're moving in together throwing wine and cheese parties wearing matching Motley Crue shirts.
Tiffany's friend Todd is a chipper. He gets invited to watch Sex in the City on girls night. And he gives he has a creepy crush on her. I can tell by the way he looks at her.