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.
What's the most competitive you've ever gotten over something completely silly?
Find late-night cosmic bowling with black lights and loud music. Order terrible bowling alley nachos and pick the ugliest rental shoes.
Bowl with ridiculous handicaps - wrong hand only, eyes closed, granny style, or through your legs. Make up new scoring rules as you go.
Celebrate whoever bowled the worst score with the 'Golden Gutter' award. Grab late-night diner food and laugh about your worst throws.
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.
Create rival teams and lists of photo challenges: strangers doing your pose, weird storefront finds, free samples collected, pigeons counted, etc.
Set a 2-hour timer and race through downtown checking off items. Get creative, talk to strangers, and document everything with photos.
Meet at a bar to tally points and share your best photos. Losers buy the first round and have to recreate their most embarrassing photo.
Set a $10-15 budget each and hit multiple thrift stores. Challenge: find the most outrageous complete outfit for your partner.
Hunt for the wildest patterns, weirdest accessories, and most absurd combinations. Bonus points if it somehow works together.
Model your outfits at home or in public if you're brave. Take photos, laugh until you cry, and maybe actually keep one weird piece.