Ok guys, there is no way on Earth I can be sure that this theory is right, but I was watching Who's Your Daddy and K and Cake think that you guys might be interested in hearing what I came up with, so here you go:

Dylan Crandall: House's friend. House knew him from the time they were 20. But then there was a convo between House & Wilson that got my attention. House was talking about a girlfriend that Crandall had. As House put it, "He (Crandall) was in love. He was always in love." As he also pointed out: Crandall wanted to marry this girl. Now, point 1: If Crandall was always in love, why did THIS girl matter so much? House did not approve. He told Wilson that he thought the girl was 'flaky' and sending 'mixed signals'. He also told Wilson that he told Crandall he would talk to her. And they 'talked'.
If you haven't guessed my theory by now, I'll tell you: I think that that girl was Lisa Cuddy. The time period makes sense. It was probably a few years after House had met Crandall, so mid-20s. Which is around the time House & Cuddy had their thing. However, it was never specified why it happened. If it was because of jealousy, not only does it fit, but that would be DAMN HOTT. Not only that, but K pointed out that Cuddy didn't know Crandall since she said "I thought I met all your friends." However, when she saw WHO it was, did she not bolt like there was no tomorrow as he came towards House?

So you guys: Am I nuts or could I be right?