Harriet crosses paths with Tom, who is fleeing Allison Janney like he would the fearsome Sasquatch she very well may be. She finally catches up with him and asks what the hell he was doing onstage, as he was apparently not very helpful in covering for the fact that they were prop-less. Tom's evasive and tells Allison she did great, and that's why she's the best. Allison says Tom's on her list. Right up there with Cal. She storms off just in time for Lucy to scurry in. She says that Matt's going out of his mind "up there." Is "up there" TV code for "offscreen, because the three leads had to cut back their episode order as an ultimately fruitless cost-cutting measure to save the show"? Pedeconference: Tom tells Lucy about how Stephanie broke up with Simon and how it's threatening their Hawaii trip. Lucy reacts to this news with a lot of hushed growling. They pass Simon, who's on his way to the green room to score some tail for Hawaii. Lucy says Simon can't just meet a girl and ask her to go to Hawaii, but Simon laughs her off, because of course he can. Man, this storyline is so stupid. Simon being taught a lesson about his womanizing ways. Is he Sam Malone all of a sudden?
So Simon enters the green room to a heap of sycophantic applause. A particularly hot blonde is all over his junk, and Simon's into her right back until he realizes she's married to the head of NBS Legal. Heh. So he continues to troll the green room until he passes by an incredibly attractive woman with giant breasts who asks if she's the one Simon's looking for. "Claire?" asks Simon. Claire is played by Tamala Jones, whom I recognized as Joy's pro-wrestling half-sister on My Name Is Earl. And I only mention the giant breasts because they leaped out of the TV screen and smacked me in the face. From their conversation, we find out that Claire was a one-night stand of Simon's, though he insists that he tried in vain to get in touch with her again. He says all he could remember of her phone number was that it was composed entirely of prime numbers, and he hired a mechanical engineer (Tom's little brother, possibly before he decided to start STANDING IN THE MIDDLE OF AFGHANISTAN) to help him in his search, and blah, blah, blah, trying to be smooth. Claire says she hears Simon's dating Stephanie (do they know each other? Do Simon's women meet Thursday nights for margaritas and Grey's Anatomy?Ooh, do they think Callie's too good for the show now, too?), and Simon says that turned out to be a pretty bad call on his part, considering she just dumped him, right before the show. Claire thinks that since he's up and trolling for ass not thirty-five minutes later, maybe Stephanie made the right call. He explains about Hawaii, and at first she's repulsed by the nerve of this guy, but just like any woman, she eventually comes around. Talk once again turns to Simon's reputation as a player that we're learning so much about this week. He's dated everyone, from Mariah to Beyoncé, but right now, he's only interested in Claire. She's totally falling for it, you guys. She asks if he really did try all the prime numbers, and it looks like Simon's sincere when he says he did. How did Sorkin resist turning that thinking-man's-quirky activity into a subplot? Anyway, Claire caves and accepts a free trip to Hawaii. What a sucker.