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Felix puts together a "dare night" that tests the limits of his new classmates. During the game, Lucas meets a mysterious new girl, Anna, who is connected to the gang in a way they don't yet know while Peyton confesses to the church that she recently did cocaine. Meanwhile, Keith is caught of guard when a beautiful woman comes to the dealership to buy a car and the two end up hitting it off and Karen goes on a date with her professor, Andy.
This is the first appearance of recurring guest stars Daniella Alonso (Anna) and Maria Menounos (Jules).
Barry Corbin (Coach Whitey), Paul Johansson (Dan Scott), and Barbara Alyn Woods (Deb Scott) do not appear in this episode.
This episode did not feature an opening voiceover by Lucas nor did it feature a "Previously on One Tree Hill" segment.
Michael Copon (Felix) and Daniella Alonso (Anna) previously starred together in All You've Got.
Lucas: Anna, I dare you to call me.
Jules: Car sales men are always such jerks. Why are you smiling?
Keith: My brother owns the dealership, I'm just helping out. I'm actually a mechanic.
Jules: Oh. I like mechanics.
Tim: Dude, check out Part 2. Get it? Dude, the hole's #2.
Nathan: There is something wrong with you, you know that, right?
Tim: What? I didn't write the dare card. Hey, give me the camera and give me some leaves, all right?
Brooke: I'm bored and ignored.
Felix: Bored maybe, but you've never been ignored by a guy in your life.
Andy: You like The Constantines?
Karen: Sure. I mean as much as anyone can like a band they’ve never heard of.
Felix: With the other dares, it appears to be a tie.
Tim: Oh no, oh no, wait. Don't forget this.
(gives Felix the picture from the golf course dare)
Felix: Dude! What the hell are you doing?!
Tim: It says it right here on the dare card.
Felix: Man, that's a typo. It's supposed to say, "Take a shot in the second hole."
Peyton: So, we never really talked about the wedding, like how you got there.
Haley: I told you -- I got dressed, I threw up at my parents' house, brushed, flossed and went to the beach.
Peyton: Okay, hard image to forget, but I meant more like, um, I don't know, how your heart got there. Marriage is big. I don't know how you trust somebody for your whole life. I can't even date somebody without an escape hatch.
Haley: I don't know if it was so much about trusting Nathan, which I do. It was more about trusting myself.
Peyton: Yeah, my old friend, self-doubt. I don't know, sometimes everything seems really simple, and then --
Haley: -- it's not?
The episode title, "I Will Dare" is obviously referring to the Dare Night featured in the episode. The lyrics of The Replacements song that the episode is named for also relate to the episode plot, mainly the final verse ("Meet me anyplace or anywhere or anytime / Now, I don't care, meet me tonight / If you will dare, I will dare"), which can be applied to the start of Anna and Lucas's budding relationship.