Robin finds herself falling more and more in love with Ted. She finally decides to tell him she loves him, but she has trouble because it's her first time telling a guy she loves him.
Meanwhile Robin's sister comes to visit, and the gang takes her to the Empire State Building. She has decided to loser her virginity with her boyfriend Kyle, but Robin tries to stop this. The gang all recount their "first times." Lily and Marshall were in college, and had originally planned to wait, but couldn't. Robin had sex with her high school boyfriend, only to discover he was gay. She says that he only "sorta" had sex with her, which leads Lily to guiltily claim that doesn't count, since she had a similar experience with Scooter. This causes Marshall to be jealous. The gang leaves in anger, and Robin's sister still plans to sleep with Kyle.
However, Robin's sister comes back and claims the reason was because of Ted's story. He supposedly lied about being in love with a girl to have sex, and then borrowed 20 bucks from her only to never call again. Robin is doubtful however, and Ted admits that the story was actually the other way around. She finally feels comfortable enough to tell him that she loves him.
The gang finally goes to the Empire State building, and Marshall admits that being in the lobby hadn't counted, thus agreeing with Lily's earlier point.
Throughout all of this Barney lies about his own first time, only to finally admit it was when he was 23, and with his mother's friend Rhonda.
Notes
We get to hear everyone's "first time" story, including Marshall and Lily's which was alluded to in the pilot. Barney's "first" Rhonda will also make an appearance later in the series.
Review
A delightful episode, even if it is Ted/Robin related. They've gone as far as they're going to go however, and their relationship will hit a dead end later. But about this episode, I just enjoyed that we got to see more about each character, and get a lovely "Love You" story. It's kind of cliche for a character to struggle saying "I love you" but it's also classic. I also like meeting Robin's sister. The relatives really help fill out the cast of minor characters and make the show feel more real. Barney's lies about his first time was also funny, and Ted being an architecture nerd is enjoyable to watch.
Ranking
9 out of 10.
Season Comparison: Season 1 vs. Season 2: "The Wedding" vs. "First Time in New York"
This is probably the hardest contest to date. These two episodes are very different and it's hard to judge them against each other. They're about the same in enjoyability, but for different reasons. The Wedding is a little bit funnier with regards to Ted and Claudia's reactions, but The First Time in New York was a more character driven episode that provided insight into our characters. Another factor in this is that I have a bias that I've always considered Season 2 to be the superior season, but the Episode comparisons have been very close. Part of me wants to give First Time in New York the win just for that reason, but that wouldn't be ethical. So I'll give the win to First Time in New York for another reason. Because the main argument comes down to comedy vs. character, and if this was another sitcom or if I was another blogger Comedy would win. But HIMYM is not my favorite television show on the air, just because it's funny, though it is. I love HIMYM for the characters, and so First Time in New York, which provides more character insight gets the win here.
Winner: Season 2 Episode 12: First Time in New York
Scoreboard
Season 1: 5
Season 2: 8
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