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Joe, an Iraq war vet, has a problem. He has PTSD, and has been referred to Claire for examination. He wakes up at night after nightmares, and has written a large bundle of letters to a girlfriend he had in high school, which he's never sent. He picks the right time to throw them away, however, in the presence of Trevor, who reads them and arranges for the two to meet again, and things go smashingly. Cue the monkey wrench, though... Trevor's job is never simple.
Claire: I don't dance.
Trevor: My theory holds up.
Claire: Fast dance, that is.
Claire: Because, I'm part of the unlucky percentage of the population that looks like an idiot when fast dancing.
Trevor: What makes you think you can't dance?
Claire: I thought I was an adequate dancer until I saw the video from my freshman homecoming... My one and only high school dance.
Trevor: Wait a minute. You never went to another dance after that?
Claire: You know, young girls are so touchy about being the object of scorn and ridicule.
Trevor: The key to dancing is lettin' yourself go!
Claire: I don't know how you arranged this, but you are playing with fire.
Trevor: Love is fire. Love is passion. That's what I play with. It's in my job description.
Joe: Robin can't see those letters. She'll think I'm some crazy stalker. It's bad enough that I kissed her.
Trevor: No, hey, look, I saw that kiss. There was nothing bad about the kissing. It was the bolting that was the problem.
Joe: I... I wanted to stay.
Trevor: Let's go back. We can tell Robin that you ran out to put money in the meter. (Joe looks at him quizzically) I can sell it. Just... whatever I say, keep nodding.
Joe: I... I can't see Peaches again.
Trevor: Why not?
Joe: It's complicated, all right?!
Trevor: Life is complicated. Love is simple.
Joe: I had a plan. And this is not in the plan.
Trevor: (on phone) ... in fact, I'm desperate for a fresh pair of skivvies, so I'll have to venture in there anyway.
Claire: Promise me this is the last status report I'll ever receive regarding your underwear.
(noticing a young couple in the shadows making out at the Prom)
Trevor: (to Clair) You see? You missed all those high school socials because you were worried about dancing, when you could have been making out the whole time. You know how to do that... don't you?
(handing request to DJ)
DJ: 'Fearless Heart'? This is a country-western song.
Claire: Yes, it is.
DJ: Does this look like a country-western crowd to you?
Claire: Flip it over.
(Flips it over, there's a $20 bill clipped to it)
DJ: (smiles) I stand corrected. It's like I'm on the set of Hee-Haw, they'll love it.
Trevor: What this is, is a hurricane with your name on it...
A hurricane is the name of a drink associated with New Orleans and Mardi Gras. In particular, it was originally associated with a very well-known bar in New Orleans called Pat Obrien's, though there are now a lot of places which sell variants on it. Pat O'Brien's even sells an official drink mix, though, in reality, the original drink was 4 ounces from whatever bottles needed to be emptied out. The official version is a sweet drink tasting much like punch, which is easy to overdo since one really does not taste the alcohol, despite actually being a very strong drink.
DJ: I stand corrected. It's like I'm on the set of Hee-Haw, they'll love it.
Hee-Haw was a long running variety show aimed at the country-western crowd. It was a fairly low-budget affair with a lot of cornball jokes and running gags, with a steady stream of various Nashville and C&W personalities doing cameos. Nonetheless, it did have its charm. One of the standard skits was people standing up in a paper-cornfield and telling classic bawdy, vaudeville-style jokes.
Robin/Peaches: I collect Hummel figurines, I knit outfits for my pug, I've seen High School Musical like 30 times... I plan to see it 30 more.
Hummel figurines are a long-time collectible made in Germany of porcelain. Typically depicting children in 1700s clothing and activities, they are considered kitschy, appealing to the common, salt of the earth type of people (which Robin clearly is).
A pug is a variety of toy bulldog.
High School Musical is an Emmy-award winning 2006 TV-movie/musical made by/ for The Disney Channel. It sparked the career of Zac Efron, and has been one of Disney's most successful TV creations.