Cut to the next morning, as Rick pulls up to the high school to drop off Jessie and Grace. Grace takes longer getting out of the truck, so she's still sitting there when a young, brainy-looking guy races up to Jessie. Rick asks if he's Tad. Grace glances and says, "No. That's Tad," as the much taller and older Tad strolls up in his varsity jacket. Rick looks a little troubled by the sight of him. This looks like the kind of kid who knows his way around a back seat, after all. Grace climbs out of the truck, and Rick tries to register the reality that is Tad. He's startled by a tap at the window, and looks up to see Jessie and Tad peering in at him. "Uh, Tad wanted to meet you," Jessie says, looking slightly mortified. Tad thrusts his arm inside the truck to shake hands with Rick. Rick tries to swallow his alarm and act normal, but he says, "Hi, Tad," just a little too loudly.
Meanwhile, over at the radio station, the Curmudgeon has called Lily into his office. She approaches, trying to head off the negativity by reminding him that he was the one who put her in the chair. The Curmudgeon holds up his hand to silence her, and cuts to it: "I figured I'd start you off small, on the weekend. When nobody's listening." "What?" Lily breathes. He adds that he wants her to do a segment with some guy that night, to give people an idea of who she is. He says people want to know about her. She's shocked. "Well, you heard about all the phone calls," he says, waving a hand in the direction of phones. "Apparently, you struck a chord. Let's hope you can strike it once a week," he says. Lily is dazzled. She starts to stand up, but then sits down to say, "Oh, but I told my husband." She catches herself, saying, "You don't want to hear about my husband." "Just on the air," he says, with a touch of pleading in his voice. He is seriously my hero. Lily spins around on her way to the door and asks, brightly, "How many phone calls?" The Curmudgeon just stares at her, tight-lipped. "I'm going!" she says and practically skips out of there. The Curmudgeon stares at the streak left by his little spitfire and allows himself a chuckle.
Cut to Jessie sitting in Dr. Wise-Ass's office. She's saying, "When I imagined my first date, I thought I'd be really excited because I would be in love. Like that song that demented Dimitri is making me sing, 'Heart Like a Wheel.' Do you know it?" Dr. Wise-Ass, who's been dipping into the Grecian Formula, asks to hear a bit of it. Jessie obliges, and the good doctor smiles warmly at the sound of her voice. Jessie says she wants to feel "like [her] heart is totally shipwrecked for someone, and [she] doesn't have any of those feelings for Tad." Dr. Wise-Ass dispenses his wisdom: "If you don't feel like going on this date, maybe you shouldn't go." Then he cracks wise, "That'll be a million dollars." Jessie tosses a pillow at him.