Robin: You know, Katie, I have wanted to come to the Empire State Building for so long, but I waited to come here with someone special.
Katie: Oh, here we go.
Lily: Marshall and I have never been to the Empire State Building either. But I'm so glad I waited to do something so important with my fiancee.
Marshall: Speaking of waiting, I signed an abstinence pledge in high school. It's totally cool to wait. And stay away from drugs, other than pot.

Katie: You told them?
Robin: Oh, okay, yes, I told them. But only because I think you should hear it from other grownups, too. Everyone thinks you should wait. Right, guys?
All: You should wait.
Barney: Sex is fun.

Katie: You are such a hypocrite. You were only 16 when you lost yours.
Robin: Well, how do you know that? You left your diary in your old room slash my new room.
Barney: I'll pay you $10,000 for that diary.

Katie: Look, I've been dating Kyle for two months now. It's like forever. I mean, we've already done everything else. I mean, we've even...
Robin: Oh. [puts fingers in ears] La, la, la, la, la....
Marshall: Even Kyle gets to do that.

Katie: Robin, this is happening. Look, I already put it up on my Myspace page. I need a clove.
Robin: You smoke now, too?
Lily: Oh, remember cloves?
Marshall: No!
Robin: No "Aw, remember cloves?" This can't happen. She's my baby sister, okay? She should be watching The Little Mermaid and drinking Yoohoo, and not having sex.
Ted: Come on, you were only 16 when you had sex. I was 17.
Marshall: We were 18.
Ted: Barney was probably 12.
Barney: [exaggerated laughing] Good one, Ted. I was, uh, six... fourt... How old were you again?
Ted: 17.
Barney: Dude, me, too.

Ted: It was on last night.
Marshall: No, it was two nights ago. "She's Like the Wind" has been stuck in my brain for about 40 hours. I just got it out. Now it's back in. Damn you, Swayze!

Lily: The point is no matter what, it's never gonna be as perfect as you want it to be.
Robin: Well, mine was terrible.
Lily: Wait, I've never heard your story.
Robin: Well, as you know, I was 16. And it was with my boyfriend Brian.
[flashback to Brian and Robin in his bed together:]
Brian: Ready?
Robin: Yeah.
Brian: This feels so right.
Robin: Oh, I know.
Brian: Oh, Robin.
Robin: Oh, Brian.
Brian: Yeah, I'm gay.
[back:]
Lily: I'm so sorry.
Robin: Eh, I should've known. There were signs.
[flashback:]
Brian: Oh, my God! My mom's home. Quick! Get under my bed.
Robin: What?! Oh, my God!

Robin: You only get one shot at losing your virginity. And even though I just barely had sex, it counts.
Lily: What do you mean just barely?
Robin: Well, he didn't dive all the way into the pool, but he... splashed around in the shallow end.
Lily: Then you didn't lose your virginity to him. Just barely doesn't count.
Robin: Yes, it does.
Lily: No, it doesn't.
Marshall: Yes, it does.
Lily: No, it doesn't. It doesn't count. End of story.

Barney: Ooh, why, Lily Aldrin, you saucy little harlot. Could it be that before Marshall took a swim, someone else tested the water?
Marshall: No. Nobody else tested the water, right? Scooter?
Barney: Who's Scooter?
Lily: My high school boyfriend, who I did not have sex with.
Marshall: I... I can't believe this. We're Marshall and Lily, when people see us, they say, "Oh, look at them, they've only had sex with each other."
Barney: No, Marshall, they say, [sad voice] "Oh, look at them, they've only had sex with each other."
Marshall: But now that's not true anymore, now you've had sex with twice as many people as I have. I knew that you were too good at it.

Robin: Katie, please. You only get to lose your virginity once. You should only be having sex with someone who's special.
Katie: Oh, please, you've had sex with, like, a hundred guys.
Robin: It's not a hundred guys. It's not a hundred guys.
Katie: I'm sure you were madly in love with all of them.
Robin: I had different levels of feeling for each of the... very reasonable number of guys.
Katie: Really. Well, do you love Ted? Do you love Ted?
Robin: I, um...