Kim Kil Whan is worried about his daughter’s future and asks Jake for some parenting advice. 
Jake and Kim Kil Whan appear to be on better terms than when they had last seen each other in "Ocarina". The two participate in a three-legged race at the K.K.W. Enterprises Picnicathlon, emerging last place. Kim Kil Whan thanks Jake for not showing off even though he knew they could have won the race. Kim Kil Whan also makes a public acknowledgement to Jake for contributing to the success of the event.
Afterwards, Kim Kil Whan reveals that he had an ulterior motive for inviting Jake to the event — to get parenting advice. They teleport to Kim Kil Whan's home, where he tells Jake that he does not know how to deal with his teenage daughter, Bronwyn, seeking Jake's insight due to his own "teenage lifestyle". Bronwyn is increasingly unengaged in school, causing him to worry about whether she will be able to achieve future financial success. He also shows Jake several skateboard graphics she had illustrated, calling them unusual. Jake expresses awe at them but says he doesn't know what to make of them yet, and leaves through some shrubs.
Later that night, Bronwyn is seen sneaking out of her bedroom window with a skateboard in hand. Jake, who had been hiding in the shrubs, follows her. He sees her with her friends (a skunk, a rabbit, a fox, and a bear) at a small skate park, showing off some of her moves on the skateboard ramp. When one of her friends point out Jake, she asks him if he is there to rat her out, but he tells her he is just there to skate. He shows off his own moves on her skateboard as her friends cheer him on. Bronwyn is impressed as well, calling him cool for a grandpa. However, when Jake brings up her slipping grades and quotes Kim Kil Whan, she responds coldly and wants him to leave, but her friends still take to him. He embarrasses her further with a childish joke, by farting and blaming it on Bronwyn, who calls him an "old fart" and leaves.
In the morning, Jake tells Kim Kil Whan that the situation is worse that they had thought, as he spoke to Bronwyn the night before and she now thinks Jake is a square. Kim Kil Whan thinks his father is losing sight of the point and suggests staying away from Bronwyn, but Jake tells him not to worry, promising not to rest until Bronwyn realises how cool he is.
That night, Jake visits the skate park again. He even brings Finn, who arrives half-asleep, and tells him to play the flute. However, when Finn begins playing, Bronwyn's friends express distaste. Jake realises they hate the flute, but since they like mash-ups, he beat-boxes along to Finn's music. This time, her friends cheer him on.
Bronwyn blows on a leaf through her hands to generate a whistling sound, getting everyone's attention. She starts to play something on her makeshift "instrument", but accidentally inhales and chokes on the leaf, inciting laughter from her friends. Jake beat-boxes to her choking coughs in an attempt to create a duet, but she is only further embarrassed when they laugh at her even more.
Bronwyn angrily declares a thrash-off with Jake. The winner will be declared undeniably cool, while the loser will be banned from the skate park. Jake agrees to it. Finn is apprehensive about this, asking him if he really wants to ban his own granddaughter from her own skate park. Eyes sparkling, Jake says he hopes so.
They all go to a larger and more dangerous skate park for the thrash-off. Even Marceline, Princess Bubblegum, and a group of forest animals come to watch. Bronwyn's friends are all in support of Jake, who seems to only want his granddaughter's approval. He points out to her his cool new hairstyle, a Greaser-esque pompadour, but to his dismay, she simply scoffs.
The thrash-off begins. They have to grind down the ramp, through the bar maze, past the big-armed worm, through the junkyard, over the log swamp and cross the finish line at the Bottomless Pit of Love. Both Jake and Bronwyn skilfully manage the trail, but Jake is slowed down by the time they reach the junkyard. From behind, he watches in amazement as Bronwyn skates up a broken Ferris wheel, does a trick in the air, and lands back on her skateboard on the other side. Bronwyn is cheered on by her friends this time. She sees Jake try to do the same and yells for him to stop, as she had taken months to be able to make that jump. He ignores her and attempts it anyway, and ends up flying off his skateboard, onto the hard ground. Bronwyn panics and tells her grandfather he's cool, wanting him to just be okay. He is injured, but happy to hear her admit she finds him cool.
Kim Kil Whan appears at the scene and opens up to his daughter. He understands that skateboarding is important to her, and that she is talented at it, but wants her to work harder at school. They exchange apologies — Bronwyn for getting carried away, and Kim Kil Whan for not coming straight to her to talk. Bronwyn tells him that while he isn't cool, he is also not uncool.
- Bronwyn's Friends
- Kim Kil Whan's Employees
- Princess Bubblegum (cameo)
- Marceline (cameo)
- Huntress Wizard (cameo)
- Jake is shown to be able to speak a bit of Spanish, referring to Kim Kil Whan using "mi'ijo," literally translating to "my son."
- In this episode, Bronwyn can control the weather and teleport with lightning. This may be from her Rainicorn heritage.
- Kim Kil Whan seems to own a business corporation called K.K.W Enterprises. The company has a real estate agency called K.K.W Realty.
- When Jake accidentally hits a swan cardboard cut-out into the Bottomless Pit of Love, he remarks that the swan was "where the pups came from", suggesting he and Lady Rainicorn used to frequent the place.
- When Finn plays the flute, Huntress Wizard appears briefly among the trees to listen.