"I'm with Cupid" is the one hundred-tenth episode of King of the Hill. It was first aired on February 10, 2002. The episode was written by John Altschuler and Dave Krinsky, and directed by Allan Jacobsen.
Bobby and Joseph tell Hank, Peggy, Bill and Dale about the Valentine’s Day flower sale at school, where girls give flowers to boys they like. Bobby admits he’s worried he won’t receive any flowers since he’s broken up with Connie. Arriving at school, Bobby immediately receives two flowers, including one from Connie. He later shows off his flowers to Peggy and Hank, and as a reward, Peggy tells Bobby he won’t need a babysitter that night when she and Hank go out for a two-step dancing contest at Ugly's Saloon. As they’re leaving, Hank and Peggy ask Bill to check on Bobby. When Bill drops by, he asks Bobby if Connie’s visiting, and Bobby reminds him they broke up. When Bill begins sadly talking about Lenore, Bobby agrees to go out to dinner with him. They go and eat at Cooligan's, and at the restaurant, Bill confides just how depressing it is being single. The more morose Bill becomes, the more shaken up Bobby becomes. The two go back to Bill’s house where an evening spent eating junk food, watching Bill’s wedding video and reading love letters eventually leaves both convinced they’ll never find love again. They return to Bobby’s house, where Hank and Peggy later find the two crying on the couch.
After Bill leaves, Hank reminds Bobby that his break-up with Connie was mutual, and insists he’ll find another girlfriend. The next day during lunch, Joseph announces he’s throwing a Valentine’s party, but a still-depressed Bobby can only talk about losing Connie. When Connie sits next to Bobby, he asks her to the party. She accepts, and Bobby begins yelling that they’re back together. Connie tries to convince Bobby they’re just friends, but finally has to tell him they should go to the party separately. At home, Bobby calls Connie, and begs her to go with him. When she hangs up on him, he grabs some chocolate, runs to the window, and smears the chocolate over his chest in the shape of heart, much to Connie’s disgust. While Bobby is taking out the trash, Bill gives him a pep talk about winning a girl’s heart through persistence. Encouraged, Bobby decides to come up with a big idea to win over Connie. At the party, Bobby shows up in a diaper and fake wings, carrying a toy bow and arrow. He announces he’s Cupid and that he’s going to shoot his arrow into Connie’s heart, but he accidentally shoots her in the eye. Connie runs off, and Joseph accuses Bobby of ruining his party, to which Bobby replies "What?! You wouldn't even be having this party if it wasn't for me. You'd just be sitting alone going, 'Dude, like, eh... I'm so bleah'.". When Bobby insists on following Connie, Joseph and several guys grab Bobby, carry him out of the party, and throw him over the fence into his own backyard.
The next morning, Hank asks Boomhauer, the resident ladies’ man, to tell Bobby his secrets for attracting women. Peggy is aghast at Hank’s plan, and when she sees Boomhauer and Bobby leaving, she insists they follow them, assuming they’re heading for a brothel. Hank and Peggy follow them to Shelwyn's, a department store, where Boomhauer begins blatantly hitting on women in the shoe department. One by one, they turn him down cold, but after propositioning 23 women, Boomhauer finally gets a phone number. Bobby is disgusted that Boomhauer’s secret weapon is merely barraging women until one finally agrees to go out with him. As Boomhauer continues his onslaught, Bobby sinks into a chair, once again depressed. He begins talking to the girl next to him, Debby, and the two hit it off. Hank and Peggy arrive just as Bobby and Debby head off together. Hank thanks a surprised and confused Boomhauer for teaching Bobby his tricks of the trade.
- Hank Hill
- Peggy Hill
- Bobby Hill
- Joseph Gribble
- Dale Gribble
- Bill Dauterive
- Jeff Boomhauer
- Connie Souphanousinphone
- Stuart Dooley
- Willa Harris
- Clark Peters (non-speaking)
- Nancy Gribble (non-speaking)
- The title is a reference to the common phrase "I'm with Stupid".
- The episode features Sum 41's "In Too Deep" song during the party scene.
- An episode of The Simpsons, which airs on the same network and the same night as "King of the Hill", was also named "I'm with Cupid". That episode was also a Valentine's Day episode, though it aired in 1999, three years before the King of the Hill episode.
- Bobby Hill: "I'm your little candyman..."