Donny Cogswell buys a video camera, then quits his job as a Wall Street stock broker, when he's about to be fired. Back at his apartment, it turns out he'd left the shower on that morning, causing a great deal of water damage, which cost him most of his savings. Then his girlfriend Janet breaks up with him. So Donny decides to do some travelling, and the first place he goes is Paris. A couple of weeks later, Janet receives a video tape from him, and starts watching it. She keeps watching it when her new boyfriend, David, comes over to her apartment. Donny is trying to show Janet how romantic Paris is, and that she should come there to be with him, but by the end of the tape he realizes she was right to let him go. David, meanwhile, has gotten fed up with her watching the tape, and leaves.

Donny sends a video tape to his grandpa Ziggy as a birthday present, which Ziggy and his family watch at his party, over Ziggy's protests. Donny meets a woman named Anna in Budapest, and travels with her on a train to Ziggy's old home village. But whenever he uses his family's original name, people get angry, and he has no idea why. Eventually, Anna, returns to explain the situation. It turns out his family was nobility, and oppressed the people of the village, so the family name was now a curse among them. Anna takes Donny to see her grandmother, who was an old girlfriend of Ziggy's. Then the villagers show up to apologize, after they found out Donny was Ziggy's grandson. Because Ziggy had given up all his wealth and power, and he was the one member of the family they liked.

In Barcelona, Donny sort of unintentionally makes dates with three different women on the same night: Anita at 7, Gina at 9:30, and Angel at midnight. None of the dates go exactly as planned, and in the course of each one, Donny manages to sustain a different injury. Meanwhile, the video is watched by Donny's old roommates, Gary and Steve, as well as their new roommate, Warren. They keep making bets about what will happen next on the tape.

Donny's little brother Larry is at college, dressed up like Lawrence of Arabia, because he's obsessed with that movie, which he used to watch with Donny alot. His girlfriend Meg shows up to watch Casablanca with him, but then he receives a tape from Donny, and he'd rather watch that. It turns out that Donny is in Morocco, heading toward Marrakesh. He and Larry always wanted to go there. But the truck Donny was riding in breaks down, and he's stuck in another city. He hires a boy named Ali to handle his camera part of the time. Donny wants to catch a bus to Marrakesh, but there are no seats left, because of all the German tourists in town. He does manage to find a ticket which someone else drops, though. He also spends some time hanging out with a bus inspector named Henri, and then Ingar, a Swedish exchange student Donny dated in high school, shows up. Along with her fiance. Apparently he often left Larry alone to go out with her. Also he's upset that she missed their prom because she

Okay, so it's not a city. I don't think a specific city was ever mentioned in this episode, in fact I don't think anyplace more specific than ""France"" was mentioned, but I'm pretty sure it takes place on the French Riviera, anyway. Donny gets a job as an au pair, looking after a couple of mischievous boys, Michael and Pierre, who make life difficult for him in various ways, and keep trying to use his camera themselves. Donny sends the tape to Jean, who used to be his babysitter.