
We’ve all been there: the boring first date where everything, even washing dishes in the back kitchen, seems more interesting than the conversation we’re having with the person at the table with us. The inner thoughts—“Why did I swipe right?”; “How did I not predict this from his lame profile photos?”; and “I should’ve known by his awkward text messages”—rustle through our minds as we look for every possible exit and think through every possible excuse to leave. Does “My dog ate my homework” work for dating?
As an improviser, I have a repertoire of improv games and exercises that I’ve been known to bring out at parties, family dinners and—you guessed it—awkward dates.
Here are three of my favorite exercises to do on a first date that is going downhill really fast. The best way to initiate playing these games is simply by saying, “Hey, I have an idea!” as if you have the best idea you’ve ever had, and then introducing the game.

1. First Letter, Last Letter
With your date, have a conversation in which each of you takes the last word the other person said and uses that as the first word of their next sentence. For instance, “Chocolate is my favorite food.” “Food makes me feel so happy when I enjoy it with my mom.” “Mom used to find me hiding in the snack closet eating candy.” “Candy gave me cavities as a child.” This exercise illustrates how often we don’t actually listen to the entirety of what someone says, and it’s fun because usually, people sound like Yoda while doing it!

2. Convergence—A.K.A. Mind Reading
In this exercise, you try to read each other’s minds and say the same word at the same time. The two of you face each other and make eye contact as you each think of a word. Once you each think of a word, count to three, and then say your words at the same time. If you say the same word, great! That’s the goal. You win the game! If you don’t say the same word, then the game repeats. This time, you each say a word that relates the two words said previously. For instance, if first you said “dog” and “house,” next time say a word that relates “dog” and “house,” maybe “Snoopy” or “family.” The game continues until you say the same word at the same time. Sometimes people guess the same word on the first try (that’s how you know you’re meant to be together), and sometimes it takes quite a few rounds to get there.
Regardless of how long it takes, it’s bound to turn your date from a dud into a delight. It’s also a helpful practice for our personal growth. We’re learning to cope with failure by accepting the failure to say the same word at the same time, taking it as a gift and moving forward to try again to say the same word at the same time. It feels magical when you say the same word at the same time! It’s one of the best feelings in the world (in addition to other great things that are magical and feel great when experienced between two people at the same time).
3. One-Word Story
This is exactly what it sounds like. Together you’ll create a story one word at a time. The focus of this game is listening to each other, letting go of our own ideas, thinking quickly and coming up with a funny story that also ideally makes sense.
I once played this game on a double date after the energy started dwindling and there started to be some heated discussions around topics everyone loves talking about, like politics, religion and zombie apocalypses. One of the guys actually suggested we play One-Word Story, and the four of us created a story one word at a time. The tone of the evening shifted from dreadful to playful, and though that relationship didn’t lead to love for me, at least we had a fun time full of laughter!

So what are you waiting for? Say “yes,” swipe right, and if the date gets dull, pull out your improv magic to turn it around and make sure you at least have a good time.
Original artwork by Mary Elisabeth
Mary is the founder of Improv4, which applies improv-comedy exercises and techniques to train business-leadership and life skills to individuals, entrepreneurs, teams and companies. Learn more at www.improv4.com.
Hey! The Bold Italic recently launched a podcast, This Is Your Life in Silicon Valley. Check out the full season or listen to the episode below featuring Hunter Walk, investor and former head of product at YouTube. More coming soon, so stay tuned!
