Valentine's Day is nigh, and Shea's lips are curling into a sneer. It's a purely consumerist holiday, so Marcus better not have done anything about it. Are they walking to school together or not? Marcus asks for a moment, then hustles into the backyard, where Will waits with a horse-drawn carriage festooned with red roses. It's time to shut it all down - Shea doesn't want anything for Valentine's Day!
On the day in question, Will finds heart-shaped pity pancakes in the dumbwaiter. Will cares naught for Fiona's empathy, because Valentine's Day is the best day of the year to hit on women. Tonight he's going out with wingman TJ to resurrect an old favorite of theirs, Sad Cupid, wherein they both act as if they've just gotten their hearts broken to get some booty. That night, Mr. Chris is just giving Fiona a romantic necklace featuring the tooth of a baby gibbon when a baby cries. It's Fiona's doula ringtone, which means her first baby is being born right now! She's about to call Will to chaperone Marcus and Shea's first in-house date, but Mr. Chris insists on stepping in. He'd love to spend some time bonding with Marcus! But when Shea mentions her disdain at being chaperoned by her teacher, Marcus accuses him of c-blocking, a term he learned from Will. Marcus wants to watch a movie and cuddle with Shea, and Mr. Chris will be totally cuddle-blocking him. Mr. Chris retreats to the kitchen, and when Marcus suggests watching a British garden comedy from the '30s, Shea pouts. Maybe Marcus should have made a Valentine's Day plan after all...?
Will proceeds to a bar half full of 20-somethings, presided over by sexy, straightforward bartender Liz, who's totally got his number. Things in the booty department don't start off well, and when TJ arrives lip locked with Chloe, a French girl he met an hour ago, they go downhill. TJ agrees to one round of Sad Cupid, but when Will casts his line, TJ is back to lip locking, scaring their intended lady targets away. Back at the house, things are going downhill with Shea, too. Marcus foregoes Mr. Chris' offer of assistance to call Will. Knowing that when a woman says she hates Valentine's Day, she doesn't mean no presents, Will sends Marcus to his present closet, designed for emergencies just like this. By the time the phone call is over, TJ and Chloe take off to have sex, so Liz offers Will a sympathy pour and a helping hand. She presents hot 22-year-old Katie and her two hot friends drinks courtesy of Will, then warns him to wait until the girls come to him. The ensuing conversation, analyzing the barflies, is kind of nice, and Will is just about to change direction when Katie invites him to join her at Club 41 for a cat party later that night. Liz explains that a cat party means Will has to dress up like a cat to get in. Before leaving, Will asks Liz for her analysis of him, and is surprised she finds it obvious he's had his heart broken... why else would he be hitting on 22-year-olds?
It doesn't take long for Shea to figure out that the talking teddy bear Marcus presents to her is a re-gift from Will, so she rips its head off. When Mr. Chris finds Marcus desperately clawing through Will's present closet, he offers some advice: Shea is unique and special, so she's going to need a gift that's unique and special. Marcus starts to panic, so Mr. Chris orders him to ask Shea for 10 minutes. Recalling their first meeting when Shea blasted "Anarchy in the U.K." over the loudspeaker, Marcus presents Shea with her favorite, a chocolate-banana shake, and a performance of her favorite song, complete with Sex Pistols wig and dropping the mic. While Shea's initial reaction is, "That was so stupid," she admits it was stupid in a good way.
After an ear-splitting hour of boredom at the cat party, Will returns to the bar to tell Liz she was right. He did have his heart broken... and how about a kiss?
