The scene opens with Penny, Dave and Brad hanging out in a café, when they start talking about the ‘breakup window’. Penny wants to break up before it is too long, and explains that the breakup window is the right corridor of time when you can breakup with minimum trouble. Apparently, her latest boyfriend has commented that her skin is very soft, and winked. That has made her wonder whether he means it, or if he is just making a pass. When Dave and Brad touch her cheeks, they suggest he must have meant it. Her skin is apparently soft like butter. Max arrives finding that weird, and later, when Brad announces he has plans of Valentine’s Day surprises for Jane, Penny warns him with a reminder how well surprises go with Jane.
On her birthday, she got so scared at her birthday surprise, that she ended up macing her friends. However, Brad knows his woman, and has everything sorted out. Before long, Max announces that Valentine’s Day celebrations will be all about riding through the city in his limousine. However, Dave is preparing to stay in – because he will be preparing a five-course meal for his girlfriend. Later, as Alex is preparing for the celebrations, Jane tells her Valentine’s Day is just a corporate propaganda so that people buy more stuff. Why doesn’t she understand the holiday spirit, Alex wonders. And by the way, St. Valentine’s lived for real. He wandered the black forests in search of his woman, and later died as a martyr under Roman rule in the 9th century. And for Alex, she has an invitation to a singles party from one of her customers. Meanwhile, Dave, Max and Penny are discussing why Dave’s girlfriend called off the movie, and why she is planning a brunch the next day. However, Dave tries to cover it up saying she might really be busy.
Brad shows his plans to Jane – the ones he is going to surprise her with – but as soon as he creeps up on her behind the couch, Jane smashes his head with her elbow. Doesn’t Brad know she hates surprises? Dave sits with Penny, and continues his denial that his girlfriend is trying to move towards a breakup window, but soon admits he is being ignored. Brad arrives at a dentist, and that too with ah spring in his step, singing a Frank Sinatra number. However, the dentist announces he has a cavity. Brad is unable to believe that, and wants no pain. Meanwhile, Jane and Alex are going through their grandma’s clothes, when Jane announces JFK once commented she was a real Chicago slut. And then down comes Alex in her grandmother’s fur coat. Back at the dentists’, Brad has been overdosed with drugs, and he is playing with kids. One of them find he is high on something, and he is – without any control over saliva, or his spine.
Before long, the limo is out, and when Alex finds her party zone, she gets off and thinks one of the cars to belong to an attendee. She looks inside, much like a hooker, and asks if he wants a party. However, inside the car is a cop, and the place looks like it has just been raided. Back in the car, Alex realizes she has to help other people find love – which his when Max is alerted. His ex has hopped into the limo with his partner. Meanwhile, Brad is back from the dentist’s, and is still high. Trying to dip a strawberry into chocolate sauce, he makes a mess, and thuds down on his face. At Dave’s place, his girlfriend has arrived, but Dave is giving her grief – over what, he is not telling yet. Later, as he works his laundry, and when she complains what happened to his plans of the beautiful dinner and all, he lets on he knows about the breakup window.
When his girlfriend looks at him surprised, he knows she was lying about being busy at work and having to pick up a friend visiting town. She wasn’t lying. She actually had a friend coming over. With whom she was planning a threesome. She opens Dave’s bedroom door, and inside was waiting a hot girl. However, Dave’s lost his chance! Meanwhile, when Max has to open the door for his ex, he hopes he will be hard to recognize, but it isn’t. The result is the ex’s partner gets livid – he has to meet another one of his men, something that never seems to stop. Before long, Dave sulks out of his place, and joins the limo ride. He lets on what just happened, and hopes he doesn’t have to be alone. And then comes high flying Brad, who doesn’t recognize the people in the car – he thinks the girls to be his old partners, and the guys some buddies from college.
Later, Max gets to his ex’s place with a gift. He wants to apologize for spoiling his date, and he has a gift for him. Most romantic of all things – he has lit up the entire porch balcony with candles for his ex. Impressed, they decide to get back with each other. Passing by are the rest of the friends, including a Brad yelling with joy like ever before. Later, as Max and his old partner get on a horse carriage, Max keeps talking, but shuts up when kissed. Looking on are the friends, when Alex tells them how St. Valentine’s body was butchered, and his heart put on display at the Roman city square – the reason why the heart became a symbol of celebration on Valentine’s Day. The episode ends.