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: Both Ted and Marshall unknowingly talked a man from committing suicide.
- 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 using it as an argument that it doesn't matter if a guy is a Nice Guy, they're still hormonal teens, even himself when younger. Averted when Ted confesses to Robin that the story was actually the other way around.
- Arc Words: "I Love You". Actually saying it is the whole point in Robin's case.
- 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".
- 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.
- 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.
- 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.
- 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 with his lab partner, but didn’t because Katie was going to find out anyway. Katie finally realized that he is a jerk because he dumped her the second she told him to wait.
- 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.
- Jerkass: Katie's boyfriend, Kyle. Aside from giving a very bad first impression to Robin by hitting on both her and Lily, he said aloud in front of her that he was going to crash with a cousin who could buy them beer. For the cherry on top, he dumped Katie because she still wanted to wait a little more 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.
- Raven Hair, Ivory Skin: Unsurprisingly, 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: It is implied that Lily is this. Marshall takes a lot of time to get over this and accept that "visiting the lobby is not the same as going all the way up".
- Theme Naming: Katie and her boyfriend Kyle
