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.
If you could have a superpower but only for karaoke, what would it be?
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.
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 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.
Each person brings a slim poetry book from home or a bookstore. Visit a cozy bar and order drinks, then take turns reading one favorite poem aloud.
Move to a second bar and try writing a terrible collaborative poem on napkins, one line per person. The worse it is, the better you're doing.
Find an open mic night or just a loud bar where you can dramatically perform your napkin masterpiece. Bow to imaginary applause.