Your pal might be going out with a girl of Caribbean descent
This is fine. I'm not averse to a spot of miscegenation.

You might run into each other near college and start chatting about her and how they're getting on.

This is also fine. Chat is good for you.

He might mention that her family lives in one of the poshest parts of the city.

Again, perfectly fine. It's not like she's a snob or anything.

He could, furthermore, point that this is because her parents are absolutely minted, and that she reaps the benefits.

Jealous, but still, it does happen (although not, sadly, to me).

He could, let us say, utter the words "Now, I'm not saying I'm a gold digger." with the most evil grin in the world plastered across his coupon.

Dear sweet Jebus do I know the feeling of laughing even harder because you know you really, really shouldn't be.
(Falstaff's Spiritual Successor, Sun 25 Jul 2010, 9:51, Reply)