Big Jay Oakerson – Sugar Baby or Calculated?! (you decide)

Big Jay Oakerson meets a 55-year-old man dating a 37-year-old woman, and what starts as a conversation about their 18-year age gap quickly turns into a ridiculous discussion about younger girlfriends, older boyfriends, sex, relationships, and an unfortunately toothy blowjob.

Jay notices the couple in the audience and immediately starts asking questions about their relationship. What's it like dating someone 18 years younger? Does age really matter? And how much personal information are these two willing to share with an entire comedy club?

As usual, Big Jay takes a seemingly normal conversation and turns it into something nobody in the audience could have predicted.

Between the older boyfriend, younger girlfriend, awkward relationship questions, and increasingly inappropriate sexual jokes, Jay turns one couple's night out into an unforgettable crowd work moment.

This is Big Jay Oakerson crowd work at its best: completely unscripted conversations, relationship roasting, uncomfortable questions, dark humor, and Jay finding the one detail that makes everything ten times funnier.

If you like Big Jay Oakerson crowd work, age gap relationship jokes, couples comedy, audience roasting, dating humor, dirty jokes, dark comedy, stand-up comedy, and unpredictable live comedy, subscribe for more full crowd work videos and clips.

Big Jay Oakerson has appeared on Netflix's The Roast of Tom Brady, hosted by Kevin Hart, alongside comedians including Shane Gillis, Nikki Glaser, Tony Hinchcliffe, Tom Segura, and Bert Kreischer.

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