Robin wants to tell Ted that she loves him, but she can’t tell him. Meanwhile, her sister visits and brings her boyfriend, and Robin doesn’t know how to react when her sister says she’s ready to lose her virginity.
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Ted almost ruins Christmas for everyone when, still carrying around anger toward Lily, he calls her a horribly disgusting name. Robin tends to Barney while he has a cold.
Barney’s brother, James (Wayne Brady), visits and Robin, the only one in the group that has never met him, is suprised. But James has a surprise for Barney that he finds difficult to swallow.
Ted and Barney discusses their viewpoints on knowing things about women. Barney thinks that the more you know the more likely you are to find a deal breaker. Ted wants to know the deal breakers right away, as Robin refuses to go to the mall to cover her secret.
Marshall and Lily drag the gang to Atlantic City to elope, and their quest to overcome the three-day wait for a marriage license crosses them with some Chinese gamblers, a ship captain, and a sexy novelty shirt.
Marshall goes on his first real date post-breakup with Lily. Not only do Ted and Barney try to warn him that this girl has got the crazy eyes, but Lily decides to do everything she can to find out about this her and break them up. Also, Barney gets a new name.
Barney seduces Marshall’s law professor in hopes of getting her to grade more leniently. Lily takes a job at Ted’s office, where she promptly steals to teach Ted’s boss a lesson.
Marshall tries to get used to being single in a world that is very coupled-oriented. Barney intended one-night-stand won’t go away. Barney uses Lily to get out of his “horrifying” situation. Lily finds a place to stay.
After Ted and Robin’s first big fight, Barney tries to convince Ted that being an architect is an easy in to picking up chicks. Lily and Robin start following his trail after discovering that Ted hit it off with a girl named Anna shortly afterward.
Ted’s parents visit New York for their anniversary and he learns a family secret. Robin worries that they won’t like her. Lily and Marshall try to adjust to the new format of their relationship now that they are no longer together.