What happens when ‘90s humor meets Gen Z reactions? Chaos… and a lot of secondhand embarrassment.

In this episode of Midlife Young, we kick things off with a hilarious (and slightly painful) “don’t laugh” challenge featuring classic ‘90s-style dad jokes—complete with a mouthful of water and zero mercy. Spoiler: not all jokes age well.

From there, we dive into another round of fashion crimes, revisiting iconic (and questionable) trends from the Class of 1996—think chunky platform shoes, goth-inspired layers, micro sunglasses, and oversized logo mania. Were they bold statements… or just bad decisions?

Then the episode shifts into something more nostalgic and meaningful—contrasting how we used to stay connected versus today. Through two stories set decades apart, we explore the difference between carefully dialing a calling card from a payphone and instantly texting from a ski resort with unlimited data and zero effort. Same message—“we made it safe”—but a completely different experience.

It’s funny, nostalgic, and surprisingly thoughtful as we compare effort vs. convenience, patience vs. immediacy, and what we might have lost (or gained) along the way.

💬 Tell us in the comments:

• Did you ever use a calling card?
• Which “fashion crime” trend did you rock (or regret)?
• And be honest… did any of those dad jokes actually make you laugh?