Two usages needed to be clarified?

Question

Can anyone tell me the meanings of the following two usages?
1、pledge week
2、You want some cheese with that whine?
if possible, please also attach the origins of these two usages.
Really appreciate for your kindness and efforts.

Answer 1

I can't tell you about the origins of these phrases, but certainly I can talk to the meanings of them.

1. Pledge week is the week during the school season when the college fraternities are looking to have new recruits pledge their allegiance to the fraternity.

2. Wine (the alcololic beverage) and cheese commonly go together. When people start whining (complaining about something), someone else close to them might ask them this question, in order to be sarcastic, and remind them that their behavior is inappropriate.

Answer 2

1. Pledge week is a period of time during which sororities and fraternities initiate new members.

2. This phrase is used when someone has been complaining and the listener asks him to stop by using a bit of sarcasm. It comes from the phrase "You want some cheese with your wine?"