Olivia returns from yet another dead-end job interview, frustrated with her bad luck. Olivia was a journalism major in college, but with the poor job market, it seems like she'll be stuck being a bartender forever.
At the bar, Rick reveals the waitresses' new outfits: bras in the shapes of soccer balls, footballs, etc., in an attempt to compete with Hooters. The ladies insist that the outfits are extremely degrading, and it's not fair that the women have to flaunt it while the guys get to wear T-shirts. Rick shrugs, explaining that he just takes his order from the boss, Jerry.
Chelsea hits it off with a customer at the bar, Tim. When she learns he's a partner at a marketing firm, she sees the opportunity, asking him if they have any copywriting jobs for Olivia. He says that they do have an opening, and he'd be willing to give her an interview if Chelsea would agree to go on a date with him. Despite his morally questionable proposition, Chelsea agrees, willing to go the extra mile for Olivia.
Later, at dinner with Tim, Chelsea's really pulling out all the stops in order to impress. The date's going well enough, until the song "Butterfly Kisses" comes on and Tim starts singing along and crying, explaining that the song just makes him so emotional. Even Chelsea has a hard time handling this one.
Chelsea evens the score for the new uniforms by ordering ridiculously tight-fitting referee costumes for Rick and Todd, pretending that the uniforms were ordered by Jerry. This pushes Rick to the edge, and he talks to Jerry, managing to get the old uniforms back for the whole crew.
Tim's feelings for Chelsea continue to grow, and Chelsea continues to date him as Olivia is stuck in an elaborate interview process with multiple rounds. Tim's ready to take things to the next level, and Chelsea can't avoid the bedroom any longer. She decides to try to repulse Tim as much as possible, wearing ugly grandma underwear, attaching fake hair to her armpits and drawing spider veins all over her legs. But nothing stops Tim, and he finds her as beautiful as ever.
An unlikely hero saves the day: Assface the cat. Tim sees the cat and realizes that's why his allergies are acting up; he's deathly allergic. Chelsea claims that Assface the cat was given to her by her grandmother, and there's no way she's giving him up; it looks like it will never workout between them. Chelsea feigns an emotional goodbye and closes the door on Tim forever.
Later at the bar, Rick calls Chelsea out on her prank, admitting that she got him good. But he then changes the bar music to "Butterfly Kisses" on repeat and locks access to the sound system, getting his sweet revenge.
Chelsea agrees to a date with a high-powered exec in hopes that he can land Olivia a job.