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Ted has been waiting for Maggie (Joanna Garcia) to become single long enough for him to date her since college. However, everytime the window opens up, another guy steps in. Previously he's given her weeks to recover from her last relationship, but this time he was ready to move in within hours after having begged her next door neighbor to give him a warning. Ted brings Maggie to the bar but is soon reminded he has a class to teach so he has Marshall and Lily watch over her like a hawk while he goes to class. While at class, Ted tries to teach about bridges but ends up just discussing whether he's ready for a serious relationship with his students.
Back at the bar distracting Joanna, Marshall is going over things that his mother sent him from their old house and discovers an old homework assignment where he writes a letter to his future self. In the letter he tells himself to drive a Camaro, never stop wearing overalls, marry a tall blonde, still slam dunk, and never sell out. When he realizes he's done none of these things he's head to GNB and Lily thinking he's going to quit, chases after him. They leave Joanna in Robin's hands. At GNB, Lily finds Marshall trying to dunk a basketball and failing. She convinces him he's accomplished more than teenage Marshall could ever dream and married a woman that looks nothing ike his mother. Trust us, it was more sweet than we're making it sound.
Back at the bar, while Robin gets up to grab drinks, Jim (Jamie Kaler) a guy who works with Maggie, swoops in and invites Maggie to some erotic photography exhibit. Robin steals the invite and drags him out, but all he wants to do is return to Maggie, especially when he hears she's single. Back at the bar, Barney, who's been trying to get laid in overalls, is watching over Maggie for Ted. However, when Maggie tells Barney she likes his overalls he calls Ted warning him he has ten minutes to get there.
Ted, Jim and Barney then begin to fight over Maggie, who Robin sends home for her safety. They all rush to her apartment to find her with her first love, her neighbor that moved away. Future Ted tells us it was the second greatest love story and they end up getting married. At least thanks to Maggie, Ted learned he's ready for a relationship again.