Bro. You’re trying speed dating. Good for you! Way to get out there and meet new ladiez. This is going to be great … IF you make a good impression.
Unfortunately, while the format of speed dating has a lot of perks, it also has a lot of PRESSURE. What do you ask that really captures a lady’s essence in only a handful of seconds? Don’t be that guy that asks “What do you do for work?” And “What do you do for fun?” You are just going to find a lot of ladies who work in offices and play in kickball leagues that way and that is NOT going to bring you to an instant soulmate. Everyone will have repeated their favorite food and movie a million times. We all know if we’re cat or dog people. Don’t make these ladies just repeat themselves over and over. Let’s spice up your life like Ginger, Scary, Sporty, and Baby (but not Posh) by spicing up your questions.
What was your favorite toy when you were little?
When someone tells you about their favorite Cabbage Patch Doll (Stuart Robert who was bald and her grandparents tried very hard to convince her to get one with hair instead but she loved him anyway and would put on her mother’s lipstick and kiss his plastic bald head) or the best Transformer (obviously the Flamefeather Sparkabot which she brought into school to show off how dope the sparking action was, and it was promptly banned from school) they light up. There are good memories with that toy, and that immediately will get the conversation going in a happy, light direction. Unless she didn’t have any toys growing up, in which case OH MY GOD, BUY HER EVERYTHING TO MAKE UP FOR HER TERRIBLE CHILDHOOD. Or just move on awkwardly to your next question.
Where do you want to retire?
It says a lot if it’s her dream to run a cute little B&B in New England or sit on the beach in Hawai’i and fly drones over paradise all day. And maybe if she says she don’t know if she’ll be able to reasonably retire because her 401K matching is non-existent and the Baby Boomers are going to run down Social Security. THEN you’ll know you’re getting a realist. Some guys like realists!
What is the funniest thing you’ve ever seen?
Not on the TV, not in your Will Ferrell movies, not in your Chris Rock stand-up special. I am talking real life. One time I took this picture of my sister where she happened to be kneeling in a botanical garden, so when the picture came out, it looks like she is emerging from the weeds like a Child of the Corn. It’s hilarious. This will tell you a lot about her sense of humor (poop can’t be the funniest thing you’ve ever seen) and sense of joy, which is important.
What would be your last meal?
Totally different from just saying your favorite meal is a cheeseburger. THIS IS YOUR LAST MEAL ON EARTH. You go all out on this one. Yes, there is a chance it could be disgusting (two buckets of KFC macaroni and cheese with hot sauce mixed in and then a gallon of butterscotch krimpet ice cream?) but also fascinating.
If you could jump into any book or movie and live there, which one would you pick?
Bro, do you want to date a girl who fancies herself more of a Hermione Granger reading her way through Hogwarts or a girl who thinks she’s more like a Rey searching for hope and adventure in “The Force Awakens”? Do you want to be around a girl who really relates to Amazing Amy in “Gone Girl” or — even worse — Hannah from “Girls?” The fantasy world she would pick for herself is very telling.
If you could change one thing about Donald Trump, what would it be?
Be forewarned: this could start a political debate. But, if she says “nothing at all!,” you know you have to get away from her fast, so it’s a great litmus test.
Who would win in a fight: Benny the Bull or Sir Foster, the Atlanta Hawks organist?
If she is unsure of the identities of either of these two, stand up and yell “That’s time! Switch!” as loud as you can.
Look, no one wants Benny and Sir Foster to fight. In fact, I want them both to stay as healthy as possible. But a thoughtful look at the strengths they would both bring to the battle is a great conversation starter.
And bro? You’re guaranteed to make a better impression just by being the most interesting guy at the event. Works both ways! High five!