Second Date Update T-shirts

Wear the cringe, sip the chaos — but let your shirt say it all. Our Second Date Update t-shirts collection is packed with funny dating shirts, awkward conversation tees, and viral quote apparel inspired by the most iconic moments from the beloved radio segment. Whether you’re repping the original Brooke and Jubal era or a fan of the Jubal Show, these shirts deliver peak awkward in the softest possible fabric.

Designed for fans of Second Date Update, Jubal Show shirts, and anyone who’s ever been ghosted, breadcrumbed, or texted “wyd?” at 2 a.m. and regretted it — this collection turns dating disasters into wearable comedy.

You’ll find:

  • Cringe-worthy t-shirts with savage quotes and unforgettable lines

  • Brooke and Jubal t-shirts that throw it back to classic Second Date Update moments

  • Relationship meme tees that hit too close to home

  • Funny breakup shirts, first date fails, and radio show fan gear

These meme shirts make perfect gifts for your single friends, podcast junkies, or that walking red flag you still haven’t blocked. Available in unisex styles, soft cotton blends, and sizes for every level of emotional unavailability.

Shop our Second Date Update apparel now and turn awkward into iconic.