Robin's worried that her little sister is ready to lose her virginity when she stops by New York, and she's also ready to tell Ted that she loves him but doesn't know how.
This episode provides examples of:
- Aborted Declaration of Love: Robin tries to tell Ted she loves him, but instead ends up saying "falafel".
- Accidental Hero: To prove a point, Ted tells a random man he loves him. The man thanks him and reveals he was going to the roof to jump. Marshall later reaffirms the man's will to live while also proving a point.
- Accidental Pervert: Ted, with heavy remorse on the accidental part.
- All Men Are Perverts:
- When Katie refused to have sex with her boyfriend, he dumped her.
- Ted invokes this that even if someone is a Nice Guy, a Hormone-Addled Teenager will do anything to have sex, even himself when younger. Ted later admitted to Robin that his personal story was actually the other way around.
- Arc Words: "I Love You". Actually saying it is the whole point in Robin's case.
- Artistic License – History:
- Just as it seems like Katie is going to disregard Robin's concerns and sleep with Kyle, Future Ted tries to convince his kids this ruined her life, and (obviously) they don't buy that he's telling the truth:Future Ted: But, kids, later that night, Katie did it, and she got pregnant... with quintuplets... and she lived out her days in a trailer park... where she died an alcoholic. So the moral here, kids, don't have sex until you're married. Maybe even, like, a year or two into marriage.Luke and Penny: Dad!Penny: Come on, what really happened?
- After Ted tells his story to Katienote , he privately admits to Robin that in reality, he was the one who got used, not the girl.
- Just as it seems like Katie is going to disregard Robin's concerns and sleep with Kyle, Future Ted tries to convince his kids this ruined her life, and (obviously) they don't buy that he's telling the truth:
- Black Comedy: Ted says "I love you." to a stranger who was going to the top to jump and now he's not going to.
- Buffy Speak: When Robin's shocked at seeing her kid sister making out with a boy, she asks "Who is this... tongue person?"
- Call-Back:
- Ted saying "I Love You" to Robin in their first date becomes a plot point.
- Ted mentioned in the first episode that he was there during Marshall and Lily's first time.
- Barney did mention he and his ex-girlfriend Shannon were saving themselves for marriage in "Game Night".
- Cannot Spit It Out: The focus of Robin's arc in this episode is that she can't tell Ted she loves him.
- Caretaker Reversal: In one episode, Robin is sick and Ted takes care of her. When he goes to kiss her, she tries to refuse, but he goes ahead anyway. Immediately after, we see Ted in bed, Robin taking care of him.Ted: So worth it.
- Chekhov's Gunman: Rhonda, the woman Barney lost his virginity to, will appear in Season 3.
- Cool Big Sis: Robin tries to be this. In some ways she is, not just the way she expects herself to be.
- The Cutie: Katie Scherbatsky.
- Dark Secret: Barney treats losing his virginity at 23 as this, as he fears it may damage his self-believed "awesome" reputation as The Casanova.
- Dating What Daddy Hates: Sister, in this case, as Robin cannot see Katie as anything but a little kid and Kyle has a skater/slacker personality.
- Devil in Plain Sight: Kyle, Katie's boyfriend, is obviously not a nice person like she believes.
- Double-Meaning Title: Aside from the episode being Katie's first time in New York, it also tackles everyone's first time having sex.
- Event Title: The episode refers to Katie's first time visiting New York City.
- Friendship Moment: After Barney finally reveals his very embarrassing first time, the gang ask him to retell the Dirty Dancing story instead.
- Funny Background Event: When Katie implies to Robin that she and her boyfriend are having sex that night, there is a large, red NO ENTRY sign behind them.
- Hard Truth Aesop: Ted tells Katie his story of losing his virginity, where he said whatever was necessary to get his girlfriend in bed and after it was done he moved on. It was a lesson that consent doesn't mean there is a real connection between two people and the emotional after-effects may not be positive. Robin comments that it doesn't sound like him and he reveals he switched the roles as that's how his girlfriend treated him, and he still sounds a little bummed about it.
- Hormone-Addled Teenager: Robin's sister Katie and her boyfriend. Also, the gang themselves sans Barney.
- Horrible Judge of Character: Katie claims that Kyle is a "nice guy", despite his obvious flaws in front of Robin. As one argument to defend him to Ted, Katie told him that Kyle could have cheated on her with his lab partner, but he told Katie he didn’t because he knew Katie would have found out. Katie finally realized that he is a jerk because he dumped her the second she told him she wanted to wait to have sex.
- Hypocritical Humor: Robin asks the group for help on teaching Katie to make good decisions. Lily comments that she's binge-drinking at a bar in the early afternoon, which Robin responds with "That's why I need your help!"
- The "I Love You" Stigma: Robin reveals that she never said "I love you" to anyone before and even calls Ted's an "I love you" slut for saying it to her on their first date.
- I Need a Freaking Drink: After Kyle dumps Katie, Robin offers her a Yoohoo; Katie accepts, if she adds Kahlua.
- Jerkass: Katie's boyfriend, Kyle. Aside from giving a very bad first impression to Robin by hitting on both her and Lily right in front of Katie, he said aloud in front of them that he was going to crash with a cousin who could buy them beer. For the cherry on top, he dumped Katie because she wanted to wait a little longer for their first time.
- Meaningful Echo: Robin finally says "I love you" to Ted without screwing it up.
- Noodle Incident: Katie implies that she and Kyle already made it to at least second base. We didn't get to hear it because Robin blocked herself (and the audience) while the story is being told.Marshall: Even Kyle gets to do that.
- Perspective Flip: Ted told Katie a slightly (by that means switching his own dialogues with Molly, his fling at that time) different story of the night he lost his virginity to give Katie an inner look at Hormone-Addled Teenager males, Nice Guy or not.
- The Place: There's New York in the title.
- Questionable Consent: Ted's story dances around this. He was making out with his girlfriend and going along with whatever she said just so they'll have sex, and afterwards bailed out rather quickly. He brings it up as a lesson that any Hormone-Addled Teenager will say whatever is needed to get there. It's later revealed that he switched the roles and that's how she treated him.
- "Rashomon"-Style: Ted told Katie that he said whatever was needed to have sex with his girlfriend, Molly, and then bailed to hang out with friends afterward, which we see in a flashback. When Robin hears the story, she says it doesn't sound like him and he admits the roles were reversed and Molly bailed on him. We then see another flashback of what really happened, and all the dialogue was the same, but Ted and Molly’s lines were switched around.
- Raven Hair, Ivory Skin: Unsurprisingly, Robin’s sister, Katie.Kyle: Looks like hotness runs in the family.
- Selective Obliviousness: Robin refuses to see her younger sister as a Hormone-Addled Teenager.
- Sex in a Shared Room: Ted was on the top bunk when Lily and Marshall had sex for the first time. He's still annoyed that they did it a second time even though he asked them not to.
- Shipping Torpedo: Robin, who hates the guy her younger sister is dating (and rightfully so).
- Shout-Out:
- Robin mentions that she remembers Katie watching The Little Mermaid (1989).
- When the gang failed to connect "the Shannon story", Barney lies to cover up his first time using sex scenes from several films such as Dirty Dancing, Fast Times at Ridgemont High, Risky Business and WarGames (despite it having no sex scenes at all).
- Technical Virgin: Robin's first sexual experience ended just as it began with her boyfriend confessing to be gay. Lily suddenly gets nervous about the implication before revealing she did some fooling around with her high school boyfriend, the reason she was so defensive was her and Marshall take pride in being each other’s only sexual partner. Marshall takes time to get over this before accepting that "visiting the lobby is not the same as going all the way up".
- Theme Naming: Katie and her boyfriend, Kyle