Hit a thrift store with $15 each and 30 minutes to pick out the most ridiculous complete outfit for your partner. No input from them allowed—trust your terrible taste.
Go to someone's place and have everyone model their outfits with full runway walks and poses. Take photos that will haunt you forever.
Order pizza and vote on categories: Most Outrageous, Best Accidental Style, Would Actually Wear This. The winner keeps their outfit as a trophy.
What's the worst fashion trend you genuinely loved when you were younger?
Create a bingo card with dive bar classics: neon beer signs, regulars arguing about sports, a dog, karaoke machine, peanut shells on floor, etc.
Hit 3-4 divey spots in one night. Check off squares as you spot them and order whatever looks the most questionable on the menu.
Count your bingo wins at the final stop. Loser buys the last round and has to do one karaoke song if available.
Book a private karaoke room. Each person writes down 5 ridiculous song challenges for the other - different genres, decades, or languages.
Draw songs from a hat and perform them no matter how badly you know the lyrics. Extra points for committing to the performance with full choreography.
End with a dramatic duet chosen together. Record a video of your grand finale and celebrate surviving with drinks.
Get tickets to a local improv show. Grab drinks beforehand and come up with the most ridiculous audience suggestions to yell out.
Watch the chaos unfold and laugh until your face hurts. If they ask for volunteers, push each other to go on stage.
Recreate your favorite scene at a nearby bar. Try doing improv with each other using random prompts from strangers.
Hit up the most outrageous mini golf course in town - bonus points for black lights and windmills. Make ridiculous bets for each hole.
Keep score with creative penalties - loser buys snacks, does a victory dance, or wears a silly hat for the rest of the date.
Celebrate at a nearby bar or diner. Toast to the winner and demand a rematch next time.