In Search of a Wedding Date

My roommate and I have a fraternity brother (let's call him "George") that is getting married next month. George is the first of the guys I went to school with to go down this path and so it is an entertaining first.

First, a little background, throughout undergrad George was dating the same girl (let's call her "Meredith") for most of his sophomore, junior and his senior year. This girl was in a sorority that was close to our fraternity. She was well known throughout the Greek community. She had a mullet. She was someone that we all tolerated, but only because she was dating one of our brothers. Then for reasons passing understanding, after he graduated, she broke up with him. And he didn't take it too well. And he didn't take her sleeping around with three other [myself not included, thank you very much] fraternity brothers, including one of his roommates, all that well.

As you can see, she went out with a bang.

Fast forward another year: after three months of dating, George proposes to the new girl (for the sake of being consistent, let's call her "Callie"). Now, six months after that the wedding invitations have gone out and my roommate and I were having a chat about who I should bring as my date:

Me: Your job is to help me find a date to George's wedding...
Roommate: What about that cute girl that you had over the other night?
Me: Nah. I've realized that finals have cramped my style.
Roommate: I understand that
Me: [After a pause] You know what would be great, I should take Meredith.
Roommate: [Begins to laugh] I think we would have to make an early exit from the wedding if you did that.
Me: Yah, but I think it would be worth it to fly that girl into Chicago and bring her...
Roommate: I don't think that you could put a pricetag on what the reaction would be. Can you imagine the shit storm if you did that?
Me: It would make for an entertaining wedding, especially since there won't be a cash bar.
Roommate: I don't want any part of this
Me: Of course you do
Roommate: I'll pay for the ticket

Maybe I should send the RSVP first...