Arriving at school one morning, the gang finds mysterious envelopes in their lockers : Felix is organizing a "dare night". The concept is simple: two teams, multiple dares. Reluctant at first, they finally all join in, after Felix convinces them to test their limits for one night.
They split up into two teams: boys against Felix and the girls. Meanwhile, Karen pays her business professor, Andy, a visit to tell him it's not appropriate for him to come to the Café for coffee every morning.
The game starts. First, Lucas, more than ready to beat Felix, has to take back female clothes... wearing them; Peyton and Haley are eating pickled-eggs; Nathan and Tim are in for a waxing session; Brooke is having dinner with Felix... and dashing afterwards; Mouth, Skills go singing "I like big butts!"
Lucas gets spotted in his female underwear by security and has to run out of the mall. Fortunately, a nice young women, Anna, offers him her help and decides to tag along with him for the rest of the evening. Meanwhile, Keith meets an attractive woman at the dealership and offers her a ride to test a car.
The night goes on. Andy and Karen decide to go out for dinner and start talking about each other. Lucas and Anna go out for a drink and when Lucas leaves her, he also dares her to call him. Peyton comes clean about her drug problem with the priest, which makes her feel better.
Skills and Mouth get risky with snakes at the zoo; Brooke spends a scary moment at the cemetery with Felix and Miss Davis starts considering the idea of giving Felix a little more consideration. Tim admits to Nathan he misses him since he got married. This confession leads Tim and Nathan's friendship to come back to where it was. Keith keeps thinking about his potential customer.
At the end, we learn that Anna is actually Felix's sister.