Ted and Barney start checking out the club scene with their friend Robin, whereas Lily and Marshall try to participate in some more "grown-up" activities, as they draw slowly nearer to their wedding.

A mysterious tape arrives for Barney from one of his numerous ex-girlfriends, and the entire gang watches it. But, in order for them all to find out how she broke Barney's heart and made him into a suit-wearing bachelor, everyone must share their most embarrassing moment.

Robin is nominated to receive an award for a news report and everyone needs a date to take to the show. Barney introduces Ted to Mary as a date that Ted can take to the show. Originally Ted is opposed to the idea of just trying to save face in front of Robin but when she shows up with a date he changes his mind. Robin asks Mary lots of questions, and Ted begins to really like Mary, despite her occupation.

Barney works with Marshall on his bachelor skills, which include hitting on women. Lily is back from her venture. Robin helps her look for a new apartment but gets sick of hearing about San Francisco.

Marshall is all set to celebrate his beloved Fiero hitting the 200,000 mile mark but it stops. While the gang sits in the mechanic's garage and waits to hear what will happen to the vehicle they think about times gone by that they have spent together in the car. We also get the story of how Ted met Marshall.

Ted and Barney pretend to be visitors to New York City to pick up women. Robin is still dating Gael.

Ted pursues a woman named Stella, but only gets attention from her receptionist Abby.

When Barney and Abby realize that they have one thing in common - their mutual hatred of Ted - the "couple" decides to go to the bar to flaunt their new relationship in Ted's face.

Ted and Stella move up their wedding date, but the wedding may not go off as planned after Ted breaks the "No Exes Rule" and invites Robin to come in from Japan for the wedding.

Ted learns that not only did Lily plant another woman's earring in his bed for Karen to find, she has meddled in some of his other relationships as well.

Lily comes up with a perfect plan to break up the relationship between Barney and Robin when they have a rough patch, but she needs help from Robin's famous friend, Alan Thicke, in order to make it work.

When Ted attends his mother's wedding, he is extremely disturbed by her overly affectionate relationship with her fiancé, which forces him to think about his own life and make an impulsive decision.

When the gang teases Robin about not being a real New Yorker, she sets out to prove them wrong by racing to catch a glimpse of Woody Allen.

Barney and Robin are afraid to break the news to Nora and Kevin that they cheated with each other and want to get back together, while Ted and Marshall get stoned together at a concert.

The gang works together to plan a legendary bachelor party for Barney.