X99.5 wants to get to know you a little better…and yes, it might be embarrassing.
We’re talking about your worst date ever — the one that still makes you cringe, the one your friends beg you to retell, the one that should’ve ended early but somehow… didn’t.
And now, that disaster could actually win you VIP tickets to Disney On Ice, coming to VyStar Veterans Memorial Arena, March 27th to 29th! Enter Yours below!
If you’re wondering “Is my story bad enough?” ... it probably is.
We’re looking for things like:
- A date who brought their ex (intentionally or not)
- Someone who lied about their age, job, or name
- A date who spent the entire night on their phone… or worse
- A moment when you realized “I should’ve stayed home”
First dates. Blind dates. Online dates. Double dates gone wrong. If it was awkward, or just BAD — we want it!
HOW TO ENTER (IT’S EASY)
Follow the instructions below, be ready to submit an MP3 or a Video telling your story!
One winner will be picked at random, but let’s be honest — the crazier the story, the better (in our opinion).
NO PURCHASE NECESSARY. 02/06/26 – 02/22/26. Open to legal FL res. Of Duval, Baker, Clay, St. John, or Yulee Counties. To enter: (i) visit our website (x995jax.com) or download the free X99.5 app and submit your video in regards to the question. One winner will be selected at random. Odds vary. Winner will receive 4 tickes to Disney on ice ($300 value) For prize information, restrictions, and Official Rules:www.x995jax.com. Sponsor: Cox Radio, LLC d/b/a Cox Media Group Jacksonville, 11700 Central Pkwy., Jacksonville, FL 32224.
©2026 Cox Media Group
