Simon hopes that Florida will be better to Robbie than Glenoak, and a picture of Robbie floats away.
And now we get to hear about Matt. Simon says he knows more about his sister's relationships than Matt's, but he was able to find some pictures of some of Matt's women. Like Heather, who Simon thought Matt would marry, or his professor, who he thought liked him but totally didn't.
Admissions Guy 1: I want to know who took a picture of Matt trying to lay one on his teacher while she cringed in horror.
Admissions Guy 2: I think the question with this family is, "Who didn't?"
There was also a girl Matt met when he was a mall Santa Claus, and then there was Cheryl, who was "interesting," which is probably another word for "whore." Cheryl and Robbie were together until Cheryl said she was pregnant to get Robbie to marry her. Simon can't believe that Matt never had sex with Cheryl, because she's hot. And that brings us to Plot Contrivance, who's totally Jewish. There's a picture of Matt and PC the morning after they got married, wearing their post-coital bathrobes. One must wonder how Simon got a hold of that picture, or, if one has seen the episode, how it was even taken, and by whom.
Simon wonders if any of his siblings' spouses will ever measure up to the CamRent standard. Kevin is a total weirdo loser who has "family money," but lives above the garage. And Carlos and Mary don't know each other very well. Simon does not mention that Matt knew Sarah not at all before he married her, because the point here is that Mary is a flighty stupidhead and Matt is awesome.
And how does Ruthie feel about all this? Something quasi-wise about enjoying journeys. She may have already found the man for her. Who could this man be? That's right, it's Peter. Simon says that Ruthie made a "good choice" in him, and he's "a winner, first time out of the gate."
Admissions Guy 1: Just like Seabiscuit!
Admissions Guy 2: Even Seabiscuit was less sentimental and boring than this.
Of course, Simon's had his share of the ladies. And someone took pictures of him making out with all of them. Now he's got Asslee, who he's in love with, even if he's not ready to be in love. He wants to do stuff before he gets married. He wants to know who he is. Allow me to tell him: he's an arrogant, self-important pervert. Now Simon can move on to more important issues. Like getting a haircut.