David wins $100,000 on Snapchat in a giveaway, one of the hometown boys loses a bet and has to work for the new pizza place, and Jason's daughter appears on the podcast. Plus, Ilya makes his mom cry, and David does the dentist.

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David loses $6,000 over Spike Ball, Jason spends time with his ex-wife's new boyfriend for Christmas, and Natalie talks about the first time she was hit on. The gang shares their experiences with prom weekend, and someone gets ditched a few days before the big day.

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David sells out of his $100,000 puzzle, the gang does Secret Santa, and Natalie loses her virginity while playing capture the flag. Ilya announces he wants a girlfriend, and gives Jason a very sweet gift for the holiday season.

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David talks about what it's like at a huge red carpet premiere, a new business endeavor, and David & his publicist get into an argument. Jason brings up his new surgery, and the launch of a pizza company!

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David is going to hire a new full time live in, Natalie gets gifted a soccer team for her birthday, and a brand gets their campaign rates leaked. David also discusses his favorite brand partnership he ever got, and Jason's first pregnancy.

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David runs into Zane giving away money, Jason comes up with a new business venture for David, and David gets pulled over. Plus, Ilya gets very mad at David for stealing his pizza.

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David brings up an embarrassing moment that happened while filming a TikTok, Jason worries about going to jail, and David attends the AMA's. Plus, David's old high school teacher talks about the time a student disappeared on his field trip

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David visits his childhood home for the last time, Ilya has a fight with David over the laundry, and Jason goes on a triple date. Plus, Natalie's mom shares how she hides from the government, and the gang goes on a fun adventure as David tries to find love. 

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David pranks Jason on national television and David's old high school teacher drops by. Natalie and Ilya share their first kiss story, and someone gets roasted during a business meeting.

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David meets with Leonardo DiCaprio to work on a job, Natalie has a health scare, and Jason addresses his prenup. Plus, the gang talks about a food challenge David had with his childhood best friend and Jason's 4 hour movie night with his son.

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