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.
When was the last time you did something that made you feel like a kid again?
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.
Research three hidden speakeasies in your city that require passwords or secret entrances. Write down clues for each location but keep the final destination a surprise.
Navigate to the first speakeasy using only your clues, embracing any wrong turns as part of the adventure. Order craft cocktails and share stories about the most interesting bars you've ever discovered.
Toast to your successful detective work and decide together whether to reveal your other speakeasy locations or save them for future dates. Take a photo with your cocktails to remember the night.
Find a food truck gathering or street food area in your city. Create a silly rule for choosing trucks like 'the one with the most creative name' or 'whatever the person in front of us orders.'
Order from three different trucks, getting small portions so you can try variety. Rate each dish out of 10 and create elaborate, ridiculous food critic reviews for each other's benefit.
Crown a winner and take a photo with the winning food truck. Follow your favorites on social media and make a pact to try a new cuisine together each month.
Plan a route through your city visiting 4-5 different restaurants in one evening, having one course at each. Start with appetizers at a place known for small plates, making reservations or calling ahead when possible.
Move through your courses—soup or salad at spot two, main course at spot three, cheese or another savory at spot four. Walk between restaurants when possible to work up appetite and explore the city.
End with dessert and coffee at a cafe or bakery you've been wanting to try. Rate each course and restaurant, deciding which one you'd return to for a full meal.