Gingerbread house architect Jeannie McQueen (Melissa Schenter) has been so dedicated to perfecting her craft, she's never taken the time to go on vacation. Basketball halftime show performances and sleeping with gingerbread in airtight plastic wrap can really take a lot out of you! Thankfully, Keith and Damon are here to help this brilliant artist have the time of her life!

Self-made professional skateboarder Dale Mommydaddy (Freddy Boyd) wants to get away from the ghosts that have haunted him since he left his previous job, which was decidedly not professional skateboarding. In fact, he may be in the market for a permanent vacation from the seedy underbelly of Underground Boston. Can he outrun his past in order to have the time of his new life? Not without Keith and Damon's expert help, he sure as shit can't!!!

High school health and P.E. teacher Mary Lou Fleischhacker (Hannah Aslesen) is a big risk-taker who has never left her home state of Minnesota. Keith and Damon talk to her about her two friends, her masturbation habits, and her fledgling entertainment career as they try to determine the right vacation for her. She may have made some questionable investments in the past, but this one is sure to pay dividends. After all, what's more profitable than having the time of your life??

Unlike many clients at Berd Product Travel Agency, Rae Ducet-Funk (Dan White) does NOT want to get away from his stepson. In fact, he wants to get away WITH his stepson! Rae's been dealing with a contentious divorce, the fallout from his controversial cameo in Avengers: Endgame, and a terrifying pasta dinner, when all he really wants to do is get to know Neal. Keith and Damon have the perfect solution: a vacation! 

Repeatedly failed business owner Sandra Tartarsauce (Maggie Winters) just dumped her boyfriend. Plus, everyone in her town hates her. PLUS, she can't even get a glass of Chardonnay because of her big rolling incident at the town bar! Sounds like she might want to... get away? Certainly everyone in her town would like her to do that! Let's see if Keith and Damon have what it takes to give this poor reviled woman the vacation of her dreams. Or rather, let's HEAR!

Omaha resident Casey Gallagher (Colleen Murphy) has never traveled anywhere - not even other parts of Omaha. Is there a perfectly innocent explanation for this? No! Keith and Damon must dig deeper into Casey's increasingly disturbing life in order to find the perfect vacation to help her get away— ideally forever!

Professional assassin Douglas Michael Stewart (Chris Longfield-Smth) wants to be there for his lovely wife and wonderful son, but work obligations keep him from being the best husband and father he can be. He's been all over the world, but always for business, never for pleasure. Could a vacation provide the pause he needs to recharge and possibly pivot to a new career? Keith and Damon hope to put "a bullet" (fun) in his "head" (life) with a "big gun" (trip of a lifetime)!!!

Small business owner and professional internet bully Kevin Funt (Jason Wenger) is stressed about work. Specifically, he's worried that some of the tweens he's bullied for work are going to find him and beat him up. Sounds like someone who needs to get away! Keith and Damon talk to Kevin about the bullying biz, read some confusing samples of his work, and learn about his exercise routine, all in the pursuit of giving him the TIME of his LIFE!