"I Will Dare" is the fifth episode of the second season of One Tree Hill and the 27th produced episode of the series. It was broadcasted on October 19, 2004. Felix organizes a "dare night" to test the limits of his new classmates. While out playing the game, Lucas meets a mysterious new girl, Anna. Peyton tearfully confesses to the church that she recently tried cocaine and Keith is caught off guard when a beautiful woman comes to the shop and begins flirting with him. Meanwhile, Karen goes on a date with Andy, her younger professor.
As a new day begins at Tree Hill Highschool, Haley, Nathan and Lucas discover cards in their lockers. Immediately assuming it must be a plan from Brooke, they look across to Brooke's lockerbut they find both Brooke and Peyton exchanging the same confused looks. As they wonder who has put the cards in their lockers, Felix walks past smiling. Meeting together, including Skills, Mouth, Fergie and Tim as well, Felix tells them all about the 'dare night' he has set up for them. All the kids are givien cards and they have to complete the dares on either side of the cards to earn points. He asks who is in and Tim is the first to encourage everyone. Haley and Peyton are first to volunteer as the rest of the students agree to join in, including Tim who wasn't initially invited. The teams are split into two, the boys and the girls including Felix. Lucas receives the first dare, to return womens clothing to different stores at the mall, whilst wearing them. As Lucas goes off, the boys split into two groups, Mouth, Skills and Fergie as one and Nathan and Tim as the other. The girls and Felix also split up into teams, Felix with Brooke, and Haley with Peyton.
Meanwhile, Karen goes to visit her new college lecturer Andy. She asks him why he has been stopping at the cafe every morning, she doesn't see it as appropriate. Andy gets Karen to realize she is jumping to conclusions and won't go round to the cafe as often, if she goes to dinner with him, Karen agrees. Lucas begins his first dare at the mall, he begins by taking off his top, revealing a bra and returning it to a woman and getting a photo as he does so. Haley and Peyton also begin their dares. They buy five pickled eggs that one of them has to eat. As Peyton discovers how disgusting they are, Haley offers to cheat and Peyton reluctantly agrees. Nathan and Tim are told to go to a massage parlor and ask for the special, Tim thinks they have got the lucky card and races in to the parlor. Brooke and Felix need to get a table at the busiest restaurant in town. As Brooke attempts and fails dismally, Felix manages to get a table, by booking it two weeks before the night. A woman goes to see Keith at the dealership, obviously nervous about buying a car she tells Keith exactly what she wants and the amount she will pay. Keith is shocked with her harsh attitude. As Lucas continues to return the clothing, he is spotted by the security guard. Skills, Mouth and Fergie begin their dares by having to get hit by a baseball. The other two volunteer Mouth to take the hit which he does, after getting thrown to the floor. Brooke and Felix are at the table where Felix tries his best to flirt with Brooke. As they talk about each other's lives, Felix accuses Brooke of having an eating disorder. Furious at his accusation, Brooke orders two of the most expensive dishes on the menu to eat. As she orders, Felix nips to
the toilet. As Nathan and Tim begin their massages, Tim is first to volunteer and is soon to find out it is a full body wax, Nathan refuses it but it is too late for Tim as he screams in pain. Lucas continues to return his clothes down to his pants when a girl spots what he is doing.
As she waits at the dinner table, Felix's phone rings, she answers and finds out Felix is sitting in Karen's cafe and tells her that the dare is to walk out without paying, which she does as a waiter shouts after her. As the security guard catches up with Lucas, he tells him to stop what he is doing when the girl who saw him distracts the body guard and tells him to run and the two run out the store together. As they get in the girl's car, Lucas is introduced to Anna and the two flirt as Anna asks to join in on the game. Nathan and Tim's next dare is to deliver cookies, as girl scouts. As they fail to sell the cookies, Keith drives past them with the woman in the car. Nathan tells Tim to get his own life when Tim begins talking about the whole situation with Haley. Annoyed Tim walks off. As Keith recovers from his surprise, the woman shows how nervous she is and crashes into an animal. Keith calms her down as she doesn't trust workers at a dealership, but Keith tells her he is a mechanic and she calms down and tells him she likes mechanics. As Brooke meets up with Felix, Brooke is furious, Felix makes her read the next card to go to the cemetery and jump in an open grave.
Mouth, Skills and Fergie are doing karaoke as their next dare. They force Mouth to take lead to 'Baby Got Back' as the crowd goes wild for the three boys. Peyton and Haley move to their next dare, getting baseballs thrown off them. As Peyton gets hit and falls over, Haley runs in to see if she is ok, the machine continues to throw baseballs
at them and she is forced to run off after getting hit. Lucas and Anna are digging for money in the water fountain. Andy and Karen are at dinner together, she tells him about the cafe expansion and Andy encourages it, flirting at the same time, much to Karen's enjoyment. Lucas and Anna continue their night of dares flirting with each other in between, they talk about who they were and Lucas says he is more interested in who she is trying to be and Anna agrees. The final dare is for Lucas to get photos took of him making out with a stranger in a photobooth, which Anna agrees to, but to get bonus points she has to do something else, which she refuses to show Lucas. Brooke and Felix arrive at the cemetery, Brooke is shocked to find out that Felix knows about her and Lucas and she says how painful it all was. Felix believes it is easier just to hook up with people, have friends with benefits as it saves the pain. Brooke is then forced to get in the open grave and Felix is forced to join her as the police pull in following up on a disturbance. Mouth, Fergie and Skills arrive at the reptile house at the zoo, their dare says to borrow a wild animal from the zoo, but all three boys are less than keen to steal a snake, especially Skills. Brooke and Feliz manage to get out of the grave with no trouble from the police. Brooke asks him what the point is in dare night, but Felix says it is to see how far people will go to face their fears
and spend time with each other. Peyton and Haley talk about the wedding and how much Haley trusts Nathan, more than herself. Their next dare is to complete a confession, Peyton agrees to do it. As she goes in with the intention to admit to having impure feelings about an animal, she ends up making her first confession admitting to taking the drugs the manager offered her whilst she looked for an all ages night and worries what her mom thinks of her. Tim and Nathan are on their final dare as Tim makes up with Nathan as he offers to spend more time with him. They have to fill a hole, number two, which Tim takes literally. Keith and the woman introduce each other properly, as Jules, and sells the car to her, but Jules is reluctant and won't buy it yet so Keith has to call her.
Karen and Andy arrive home, still worried, Karen checks that it isn't misread signs at the cafe, and Andy agrees that it is nothing more than coffee, although his face is a little less convincing. Lucas asks Anna to meet her friends, but Anna says not yet and takes the photo booth pictures so Lucas can't earn bonus points. At the cafe as they all meet up, the girls are leading in points, as Mouth brings in a turtle, the points even up and the tie breaker is to kiss a member on the same team. A smug Felix, thinking he is getting a kiss from Brooke, is stunned when she chooses Peyton over him. So the girls win, if no one got the photo booth picture. Lucas looks at them and then puts them away letting the girls win.
As Nathan, Tim and Haley arrive home, Nathan asks Tim to stay to spend more time together. Felix walks Brooke home and Brooke asks if he reads people so easily what he thinks of her. Felix is still unsure and wants to spend more time with her, he offers her his friendship, and Brooke says she will see. Felix then offers to be friends with benefits but Brooke refuses, repulsed by the offer. As Felix arrives back home, he speaks to Anna, his sister. As Karen asks for a CD by the Constantines that Andy was talking about as she wants to be daring. As Lucas gives her it, he puts up a photo of him and Anna.
- "It's called dare night. 1 night. 2 teams. Multiple dares. Each envelope contains a two part dare"
- "All anybody does in this town is brood and pout and get married"
- "Haley James Scott! We don't cheat!"
- "Well, you did with Lucas"
- "Don't make me smack you!"
- "Go to the cemetery and take a photo in an open grave. That's perfect, since I plan on killing you anyway"
- "I think we get bonus points for that"
- "But isn't who you were part of who you are?"
- "Maybe, but I guess I'm really saying that I don't really need to know the person that you used to be as much as the person that you're trying to be"
- "What is the point?"
- "The point is simple, to see how far you'll go to face your fears. Sometimes you do things you wanna do because calling it a dare makes it ok for a night...like spending time with me"
- "Actually, I haven't been doing very well lately. This is the first time I've been in a church since my mom died. I think about it everyday. I just, I wonder what she would say to me right now if she could see me and see how I've been living and I wonder if she knows most days I fall short of being the person she wanted me to be or I wonder if she saw me do that line of coke last week and the thing is, I don't even know why I did it. You know my life is pretty good, it is. But I was just searching for something to make it great just something to make it matter, so, I don't know, last week, when I had the chance to change that and it was right there in front of me, I guess I was just scared to let that go. But I know it was wrong and I want my mom to know that and I want her to know that I am not that person and I'm not going to be"
- Peyton Sawyer whilst making a church confession
- "Don't you miss your Tim time?"
- "Do I miss hanging out with you? Yes. Do I miss you saying things like Tim time? No."
- "Anna, I dare you to call me"
- "So, how do you read me?"
- "I don't know about you yet, I'm gonna have to watch you a little more"
- "I thought I'd try something daring"
- "16 Below" - Light FM
- "Endless Shovel" - Rogue Wave
- "Welcome To The Movement" - Dee
- "The Keys To Life Vs. 15 Minutes Of Fame" - Atmosphere
- "Everything Is" - Nectar
- "Funny Little Feeling" - Rock 'n' Roll Soldiers
- "Good Time" - Walkie Talkie
- "I'm Sorry" - Black Toast
- "Somersault" - Zero 7
- "Dare You To Move" - Switchfoot
- "Hey Sugar" - D'Lovely
- "Collide" - Howie Day
This episode's title originated from the song I Will Dare, originally sung by The Replacements.
- Dan, Deb and Whitey do not appear in this episode.
- This is the first episode in which Dan doesn't appear.