Mr. Chris and Fiona stroll home after a romantic date, but when he asks to come in, she panics, taps him on the nose and says, "Boop!" Even more embarrassing - Will watches the whole thing from behind a tree. Once Mr. Chris is gone, Will ridicules Fiona. She admits she's nervous because she hasn't slept with Mr. Chris yet. In fact it's been years since she's done IT, and she's out of practice. Will has a warning for Fiona. If she doesn't get over this hurdle, she might just lose Mr. Chris for good.
The next morning, Will returns home from a jog and gets the scare of his life when he finds a strange homemade Marcus/Will Frankenstein sculpture, complete with Will's actual human hair. Marcus made the monument to their friendship to commemorate their upcoming "manniversary." Will, unaware of their manniversary - and the very existence of manniversaries in general - lies and says he got Marcus exactly what he wanted, which leads Marcus to believe Will purchased tickets to the Golden Gate Femme Fest, a folk festival of iconic female singers! What? Will commits to the lie, boasting that he got VIP tickets. Now Marcus is convinced he's going to meet his favorite singer, Lisa Loeb. Ecstatic, he runs off to find something to wear. Will isn't sure exactly what just happened, but now has to deliver or face Fiona's wrath.
Turns out, Andy has tickets to the sold-out show but he refuses to give them to Will - the show is too important to Laurie, plus folk music makes her freaky in a good way. This is TMI for Will, who heads off to hit up a connection for tickets. Meanwhile Fiona goes to Marcus' school to invite Mr. Chris over for a second chance at the sex. He takes her awkward hints and accepts.
Before her big night, Dakota gives Fiona a sexy makeover, complete with Brazilian wax, lingerie and super-sexy stilettos. Between the wax burn and the too-tight boots, Fiona can barely walk. By the time Mr. Chris arrives, she's hobbling around, chugging Chardonnay to ease the pain. Meanwhile Will gets Marcus into the folk festival where Andy and Laurie are enjoying a variety of pot-laced baked goods. After paying off the bouncer to get Marcus into the VIP section, Will suggests trying to sneak into Lisa Loeb's trailer - which is when the guys get caught by security. Will admits he never had VIP tickets. Marcus relays Fiona's advice: never meet your idol because it could only be disappointing. Besides, Will has become his idol.
Back at the house, Fiona's charade is also failing. When Mr. Chris attempts to take off one of her boots, it pops off like a cork, the stiletto heel stabbing him in the face. Blood everywhere. Not hot. Fiona comes clean; she's out of practice, a bundle of nerves. Mr. Chris assures her that he's looking for more than casual sex. He's serious about her, and he can wait. But after his sweet words, Fiona can't. It's on.
At the Femme Fest, Will and Marcus are about to call it a day when Lisa Loeb suddenly appears. Will begs her to talk to Marcus, but when she realizes they were the guys trying to get into her trailer, she calls them perverts. Fortunately, Marcus is impressed Lisa Loeb called them anything at all. All and all, it's a successful night and everyone goes home happy, until the next morning when Fiona disgusts Will with her post-sex victory dance.