Paul opens his office door, and the douchebag I described in the recaplet as a young Tom Cruise with Peter Gallagher's eyebrows enters. (Judge for yourself on the looks, but the voice and mannerisms are freakishly Cruise-like.) Anyway, the guy is a classmate of Paul's from Princeton (looking and acting the part rather well) who also happens to be versed in the fine art of selling drugs. When "Jeffrey Graves" tells Smith that he's looking at the "two great coxmen of Princeton '55," Smith hilariously replies, "Oh, the times you must have had!" Being part of a team with Kurt, I can't imagine he wasn't throwing some innuendo out there, but veiled accusations of High Ivy homosexuality quickly give way to the business at hand: Buying weed. As he talks price and gets out a jay (already rolled for maximum customer satisfaction) he mildly notes that Paul never calls him these days, which is either a sensitive, halting attempt to identify and repair whatever's broken in their relationship, or an inquiry as to whether Paul's been using another dealer. Smith then thoughtfully uses Paul's sweater to block the smoke from sifting out under the door, and since they were just on the subject he's the one that should have been the coxswain -- Michael Gladis slouching is still significantly taller than Patrick Cavanaugh. Smith eagerly asks for a toke, but Jeffrey tells him to relax, and then turns to regard the view: "You ever look out this window?" He's not facing Paul, but if he were, he might read his facial expression as, "This is why I never call you, dickhead."
As a peppy brass version of "Swing Low, Sweet Chariot" plays, after a long pan past a table set up with enough silver mint julep cups to bourbonize the entire actual Kentucky Derby, we see Betty and Don have arrived. Once under the enormous tent, they have a look around, and it's not long before Pete, Trudy, Ken, Harry, and Jennifer have made their way over for a greeting. Pete and Trudy, unsurprisingly given their upbringing, are the most comfortable of the lot in the highbrow situation, but Harry looks like he'd rather be anywhere but there, while Ken is wishing he'd tried harder to get a date. Jennifer, who at least seems at better ease than her husband, eagerly asks when Betty is due, and Betty favors her with an answering smile: "Any minute. Can't you tell?" Heh. Trudy then suggests they tour the place, and takes Betty by the arm and leads her away, significantly not pulling Jennifer along for the ride. As Don lights a smoke, Pete points out a couple of high-powered guests they might want to target for business, but Don merely pats his arm as he walks away: "Don't hand out your card." Probably good advice, but I'd keep an eye on Ken to make sure he's playing fair as well.
Carla is tearing up the house looking for the missing money, and when Gene opines she's being ridiculous, she somewhat hotly tells him she's not the thief. He tells "Viola" to stop it, and after she tartly correct him, he asks, "You know Viola?" Carla says she doesn't, but she'd be happy to call her and get her up to Ossining so they can take turns kicking his ass. Some of that wasn't explicitly stated, but the meaning was plain. Sally then emerges from another room, and Gene accusingly asks her if she's already done looking. Sally gives an "Oh, shit" nod...and then heads back into the room. Heh.
Peggy wakes up from a nap on her couch. Cut to outside her office, where she picks up the sandwich Olive got for her as she asks her if the boys are still there, which I guess means she never actually got that blender to them. Good for her, although the frappés did sound delicious. Olive then disapproving says she knows what they're doing in there, and since they obviously don't want to work, she should just go home. But Peggy, intrigued as you or I would be, heads off to see what all the fuss is about, and it's so perfectly Peggy that she's never even tried weed and yet she's going in with ammunition against the munchies she's sure to have quite soon.
Inside the office, stoner-speak is happening when there's a knock at the door, and Jeffrey grumbles, "Is it that old lady again?" Heh. Her "I know what they're doing in there" is close enough to "I know. What's going. On." that I wonder if she then went full-on Frances McDormand and was like, "Don't do drugs!" Anyway, it's of course Peggy, and the boys let her in; after Jeffrey smarmily introduces himself, some babbling from Paul gives way to Jeffrey asking Peggy her name. Peggy looks around proudly: "I'm Peggy Olson, and I want to smoke some marijuana." Seconded! Paul gruffs that she won't like it, but she points out that he has no idea what she'll like; her opinion is only asked in matters of "brassieres and body odor and makeup." God, even she's taller than poor Smitty. Jeffrey smooves that he'd like to know her opinion about a lot of things, and height issues or no, Smitty's response of "Jesus, give it a rest" makes me realize he's stealthily becoming one of my favorite characters. Anyway, Paul, being marginally in charge of the weed, finally nods his assent, and Smitty, who needed no convincing to begin with, lights a joint for Peggy while asking Paul if he can believe it. Paul, warming to the situation, smiles as Peggy tokes away...
...and we cut to Roger singing "My Old Kentucky Home" in blackface. And although it's not like blackface was gone in this time, I think this might be meant to underscore the idea that Roger does not have the best judgment. I know this comes as a shock. However, most people seem to be enjoying the show, although Pete looks mildly disapproving of the racist humor, while Don can't stomach it from both the narrower angle of seeing Roger make an ass out of himself yet again, and from the broader one that's about to be explored with an old geezer in an empty bar. He asks Betty if they can go, but she, having been raised to believe she was a princess and taught that "conversation is an art," is far more in her element than he, and wants to stay. He starts to head away, but she calls to him not to disappear, as she wants to dance. Roger is still singing, though, so Don vacates the area...
...and heads inside the clubhouse, apparently, in which he finds a bar with a solitary older man behind it. Mistaking him for a bartender (his white jacket adding to the confusion), Don asks for an Old Fashioned, but the guy isn't working -- he just came to raid the place and get away from people, but he can't find any bourbon. Well, with the ten thousand mint juleps already drunk, a third of them by Roger, it's no surprise. Taking matters into his own hands, Don hops over the bar, finds some rye, and makes two Old Fashioneds himself as the old coot introduces himself as "Connie" and asks who Don's escaping from. Don sighs that he's "at work disguised as a party," and Connie tells him he's in the same boat with a wedding. Connie goes on to reminisce about his childhood, and since his speech isn't all that rife with significant moments I'm going to just tell you that the guy started from modest upbringings, and then skip ahead to the part where he asks Don if he's seen "A Midsummer Dream, with Mickey Rooney." Don corrects him on the title, to which Connie responds, "God, you're prickly!" Your point, Old-eron? Oh, it's that he feels out of place at these things even though he's rich, and Don in turn relays a story of how he used to park cars for rich people at a roadhouse, and he wasn't allowed to use the bathroom they used, so when he needed to piss, he'd do it in one of their trunks. Better than in the gas tank, I suppose. Connie chuckles, and then asks Don where he comes from; Don answers Pennsylvania by way of Illinois, as they lost their farm