When Sheldon watches a romance film in a movie theater, he gets an idea about how to make Jenny realize that she loves him; he tries to make her jealous by paying Pteresa to be his girlfriend. Meanwhile, Jenny has a screw loose in one of her ponytails, which interferes with her advanced auditory systems. She continually tries asking Sheldon for help, only to find him showing off with Pteresa.
The plan backfires when Jenny is inspired to ask out a popular boy instead, named Sebastian, and she suggests a double-date, which Sheldon is forced to agree to. Even though he's broke, Sheldon can't back down or he'll risk losing all of his money for nothing. To get the cash, he puts almost everything that he owns into a garage sale, including a time machine that took 9 years to develop, and a special gift, a mechanical flower built for Jenny.
At the restaurant, Sebastian gives Jenny the artificial flower, which replaces the screw in her ponytail and actually improves her hearing further. Jenny is elated, but Sheldon becomes angry when Sebastian lies about where it came from. Sheldon tries to get a confession out of him, but Sebastian is more interested in talking to Pteresa. Then Jenny argues with Sheldon for being rude, until the two popular kids leave together, effectively dumping their respective dates. A mishap causes Jenny to leave alone, but when she looks at the broken flower, she realizes that Sheldon created it, and she begins considering him in a new light.
The next day, she goes to Sheldon's house, to find out what Pteresa saw in him that Jenny hadn't noticed before. Sheldon immediately apologizes and explains what happened, while he repairs Jenny's loose ponytail with her missing screw, but she only hears the last thing that he says. Then Jenny storms off, believing that he rejected her, because he thinks he could do better. Sheldon tries to catch her, but accidentally destroys his underwear in the process, leaving him stranded behind a bush in his front yard.
Pteresa walks by, holding hands with Sebastian. She tells Britt and Tiff that popular people always win, but a quick flash-forward to 20 years in the future shows the girls don't have a good life. In the background is Tuck, sitting in the time machine, who laughs as he sees their fate, before going back to the present.
Brad: Uh, Sheldon. You tried that already. Ms. Wakeman says Jenny is not for sale.
Sheldon: Don't you usually show up outside Jenny's window, to give her unsolicited advice?
Brad: Eh, I'm an equal-opportunity annoyer.
Sheldon: I'm not trying to buy Jenny. I've got a better plan.
Brad: You finally going to give her that doohickey you've been working on all year?
Sheldon: Nah, gifts are old hat. The thing that motivates today's woman is jealousy.
Pteresa: A double-date? No way you could afford that.
Sheldon: Oh, please? If I don't pull this off, my whole plan will be for naught.
Pteresa: All for what?
Sheldon: You know, worthless, like a bikini sale on the ice planet of Klandathor? Trek Wars, volume nine, episode 32.
Pteresa: I told you. I don't speak geek.
Brad: So, how exactly did getting rid of everything, but your underwear, get Jenny?
Sheldon: Don't ask.
Disheveled Mother Pteresa: Come on, Sebastian Junior. We got to bail your dad out of jail again.
Obese Britt: You should've married Sheldon.
Ugly Tiff: You'd be a billionaire by now.
- Jenny realizes that Sheldon could be boyfriend material after all, but loses interest after a misunderstanding at the end of the episode. This isn't addressed, but presumably the two made-up off-screen and remained friends.