First Time in New York

After some time of dating, in 2007 , Robin finally realizes that she is in love with Ted but cannot bring herself to say it, as she has never said "I love you" to a man before.

Robin's sister Katie is coming to visit New York for the first time, and Ted suggests that he and Robin take her to the Empire State Building. When Katie arrives, Robin is surprised to see that she is with her boyfriend Kyle, who is in town visiting his cousin; Kyle is immature, obnoxious and calls both Robin and Lily attractive in front of Katie. Katie tells Robin she's planning on having sex with Kyle, which terrifies Robin.

The gang takes Katie to the Empire State Building, which becomes the basis of several metaphors for sex throughout the episode, including several overt ones the gang use when Katie arrives to attempt to discourage her from having sex. Katie is annoyed by this and accuses Robin, who lost her virginity aged 16, of being a hypocrite. After Robin tells Katie to wait for the person she loves, Katie asks Robin if she loves Ted, sparking an argument between the couple.

Meanwhile, the other characters recount when they lost their virginities. Lily and Marshall, minutes after agreeing to wait and make their first time special, have sex in their college dorm room while Ted is uncomfortably sitting in the top bunk. Robin lost her virginity to a guy who admitted he was gay barely after initial penetration. Barney attempts to pass off Dirty Dancing as the story of his first sexual encounter, which confuses the gang.

When Robin tells her story, Lily says it didn't count since as sex, which the rest of the gang disagrees with. Soon enough, Marshall realizes that Lily didn't lose her virginity to him, which upsets him. They get into an argument since Marshall has always believed that they lost their virginities to each other. Marshall believes that Lily losing her virginity to her ex-boyfriend rewrites their history and changes their story as a couple.

Ted manages to convince Katie to stay a virgin by telling her that when he was 17, he told a girl he loved her solely in order to have sex with her, and then never contacted her again. He later admits to Robin that the story happened in reverse: the girl pretended to love him in order to get sex. After he admits this to Robin, she finally says "I love you" to Ted.

At the end of the episode, the group takes Katie back to the Empire State Building, and Marshall says that the last trip didn't count because they didn't get out of the lobby. Lily points out that, by that logic, he is the only one she's had sex with. Later that day, after Katie has left, they go to the bar and beg Barney to tell them the real story of his first time. He tries unsuccessfully to describe sex scenes from various movies before admitting that he was 23 and it was with his mother's 45-year-old friend Rhonda, who called him Barry the whole time. Realizing how much this embarrasses Barney, the group decides to pretend they never heard the real story and decide to stick with the Dirty Dancing story.

In a review for IGN, Staci Krause described the episode as "fantastic" and "a great episode full of humor", giving it a rating of 8.7 out of 10.[1] Robin Pierson gave the episode a more mixed review on The TV Critic, summarising that it was "A solid story with some poor jokes" and giving the episode a rating of 59/100.[2]

• "First Time in New York" at IMDb
• "First Time in New York" at TV.com