Kenan resolves to become more audacious after reading a Hemingway novel, climbing atop the Sears Tower with Kel to declare his love for a girl. However, things get complicated when Kel accidentally gets them stuck up in the tower.
- Abhorrent Admirer: Kel becomes this for a inuit man he brings to stage and a man named Brian who saw Kenan's torn sign becomes this for the latter.
- Closest Thing We Got: Kenan decides to meet two of his life goals at the same time by climbing a great height and performing a Grand Romantic Gesture. Since Mt. Everest in in Nepal, he goes for the Sears Tower instead. To be fair, he does balance it out by taking the staircase.
- Desperately Looking for a Purpose in Life: Kenan and Kel become determined to set goals in life, some of them are: Kissing a girl, meeting an Inuit putting a sign on the Sears Tower saying "Kenan ❤️ Brianna".
- Didn't Think This Through: Once they reach the top of the Sears Tower, Kel points out the door to the roof may be locked. Kenan has to resort to kicking the door down to save his plan.
- Forceful Kiss: Kenan on Brianna and Kel on Mrs. Quagmire (an old lady) before leaving to fulfill their goals.
- Grand Romantic Gesture: While Kenan just met Brianna, you got to admire his commitment to climbing the 110 story Sears Tower rather than use the elevator to prove it.
- Ignored Aesop: Kenan says they learned a valuable lesson, and Kel points out that they should be patient and not go after all their goals at once. Despite this being a good lesson to take from their experience, Kenan admits he learned nothing.
- Insane Troll Logic: Kenan and Kel flip a coin to see who can be rescued first, Kel accidentally flips the coin off the Sears Tower, but still claims he can see it.
- Long List: Kel's life goals are 37 which range from reasonable (invent a new soup) to comically nonsensical (spank a walrus).
- Mistaken for Gay: Kenan, due to accidentally ripping the letters "na" from his sign, and in the ending is approached by a tall guy named Brian.
