21 Questions: Go Deeper On First Dates

by Allison Isaacson

First dates can be nerve-racking and as Valentines Day is imminently approaching, the pressure mounts to make a good impression. We want to be ‘double take’-worthy, but we don’t want to look like we tried too hard. We don’t want to be so late our date thinks we’ve stood them up, but we don’t want to seem too eager either. We want our date to like us for who we are – not some constructed illusion. And most importantly, we want to have enjoyable conversation but forced small talk can be very stressful. How do we navigate this?

Some topics are typically no-go areas for first dates – intense religious discussions, divisive political issues, and ex-boyfriends/girlfriends among them. And of course, don’t get any bright ideas about playing “Marry, F***, Kill.”

Whether we like it or not, easy conversation does not always flow naturally. Maybe it’s our nerves. Maybe it’s our complete lack of connection, but let’s not jump to conclusions.  To help liven up your first few dates with a new flame, skim the following 21 questions and consider interjecting a few into conversation. Some of these questions are quirky or atypical, but that’s the point – to give you a unique glimpse into your romantic prospect. Happy dating!

  1. If you could be a character in any TV series or movie, which would it be?
    Would he or she want to be a certain character or jump into certain storylines? Does she want to take a walk in Khloe Kardashian’s shoes? Does he want to live vicariously through Harvey Specter from Suits? Perhaps he’s always wanted to get in on the action of The Fast and the Furious movie series or the craziness of the Jackass movies.
  2. Who are your top three music artists, groups, or bands?
    New Kids On The Block, Phil Collins, and the Spice Girls – He or she might like to relive the ‘90s. Tupac, Biggie, and Nas – Pretty straightforward. A person’s music taste can reveal quite a bit. You might have an affinity for the same artists or a complete lack thereof. But you’re open to expanding your musical horizons, right?
  3. What’s your favourite song?
    This question will likely give you insight about his or her outlook on life. “Where Is The Love?” by the Black Eyed Peas – socially conscious. “Smokin’ on Purple” by Lil Boosie – that’s a given. “Something in the Water” by Carrie Underwood – you have an idea of their religious beliefs without actually going there.
  4. Do you have any pets?
    He’s a dog person. Hey, me too. Let’s go to the dog park.
    She’s a cat owner. I’m super allergic. Shit.
    He has four Komodo dragons and a tarantula. Hmmm…
  5. How would you describe your dream career?
    Get a glimpse of his or her aspirations, goals, and desires. Are the answers flat out boring in your opinion? Does your date seem to lack ambition or vision?
  6. What are your favourite foods?
    This can give you second or third date restaurant ideas. Or if you’re feeling brave, you could even put your chef hat on and cater to his/her specific tastes. She’ll be impressed if you remember her culinary preferences.
  7. If you could give $1,000,000 to any charity or to benefit any cause, which would it be?
    You might discover your date has never taken an interest to charitable causes and doesn’t know where to start. Hopefully, you’ll be introduced to your date’s special interests by asking this question. YMCA – What makes you want to support their mission? NRA – Are you so far as armed right now? Sex trafficking prevention and victim advocacy – How’d you first gain interest?
  8. If you could live a day in any person’s shoes, who would you choose?
    You may learn about what type of person, career, or lifestyle piques their interest. You may uncover who’s a role model of theirs.
  9. What do your friends and you do for fun?
    Camping – My friends and I love to get away from the city, too! Sailing – I love the water! I used to sail as a kid. We should do it together sometime. Video gaming – To each their own; I need time to get pampered or go shopping with my girlfriends anyways. Your date might have “small circles,” sticking to friends’ events and dinner parties. What do these activities say about your date’s circle of friends? We’re oftentimes a reflection of our closest friends.
  10. When you’re spending downtime by yourself, what are you typically up to?
    She’s addicted to Netflix. You can’t stand spending time indoors – something to consider. He likes to travel. Hey, me too! Is she schmoozing the bar scene? Is he helping at the local Boys & Girls Club? What a person spends his or her time doing is who they are. Intentions are notable but actions are meaningful.
  11. How do you usually spend time with your family?
    Does your date stay in touch cross-country via FaceTime? Does his/her family live close by? She golfs with her dad and watches The Voice with her mum. He has the occasional planned “family night” – dinner, movies, and games. Maybe they have very little familial communication but have many ‘friends-turned-family’ in lieu of that. This question will give you a glimpse into your date’s family life.
  12. If you named one child after a family member, who would it be?
    He could choose his “bad ass” uncle Jim. Perhaps he’d select his dad so his son carries on the family name/legacy, Daniel Scott Kingsley. Maybe she’d name a daughter Violet after her saint-like grandma. Your date could opt out, unable to foresee a child in his or her future. This question will give you insight into your date’s relationship with family as well as his values.
  13. What’s your favourite holiday?
    Hanukah – You’ve gained religious insight. You both “go all out” for Halloween; celebrating together could be fun. The Fourth of July/Independence Day – Do you like to grill out? Do you love fireworks? Do you consider yourself particularly patriotic? Look beyond the holiday’s face value to dig for what it represents to your date.
  14. If you could eradicate the world of anything, what would it be?
    Mental illness, spiders, cancer, autoimmune deficiencies, firearms, hunger, bigotry, terrorism, communists – this question could lead anywhere. And you’ll be heading there with one more nugget about your date’s passions or concerns.
  15. If you could change any event in history, what would it be?
    He’d make the Cleveland Cavaliers win the Larry O’Brien Trophy in 2015. She’d erase The Holocaust from history (and therefore history books) if she could. He’d prevent the Industrial Revolution; he wishes everyone lived “the simple life.” Get an idea of what your date cares about.
  16. What’s your favourite store?
    REI – Outdoorsy or active. Hopefully you like to get outside and break a sweat.
    Versace – “Oh, you fancy, huh?”
    Baskin Robbins – Note to self: He or she has a sweet tooth.
    Boutiques or thrift stores – Your date probably doesn’t strive to look or dress like everybody else.
  17. If you had unlimited travelling funds for a month, where would you go?
    What draws your date to these areas? Do you have your eyes set on any of the same places? Perhaps your date is domestic and prefers staying within U.S. borders, while you have a severe case of international wanderlust.
  18. What’s a habit you’d like to break?
    Will your date be vulnerable enough with you to expose a perceived weakness of theirs? Will you?
    He eats laundry detergent. Wait. What? I don’t think this is going to work out…
    She wants to stop smoking. Maybe smoking was a deal breaker for you in the past.
    Your date has acknowledged change could do him/her some good. Will you see past the habits and appreciate the honesty?
  19. What was your favourite movie or TV show as a kid?
    It’s possible your date’s family didn’t have a TV in the house. Otherwise, who doesn’t like to reminisce about some good ol’ throwbacks? Rocket Power made him take up skateboarding and dream of the living on a coast. The Powerpuff Girls and Kim Possible inspired her to be an ass-kicking female. You think Legends of the Hidden Temple is untouchable by other game shows; he argues for Figure It Out. At least you two can agree on Jumanji and Jurassic Park.
  20. What’s the “craziest” thing you’ve ever done?
    With this question, you can learn a lot. Maybe she’s always been extremely organised, became overly obsessive, and finally stopped labelling her office supplies… Crazy. Perhaps your date is on the more conservative side and considers moving away from home his ballsiest move yet. She went streaking through campus with her senior class. He got a tattoo of his crazy ex-girlfriend’s name. See what your date will fess up to.
  21. If you could spend a day with any three people in the world, who would they be?
    Bill O’Reilly, Jedediah Bila, or Sarah Palin – they’re interested in news or politics. They’re likely “conservative,” simply intrigued by punditry, or a viewer of Fox News. You have an assortment of interpretations and follow-up questions, yet you didn’t outright ask about political views. Or maybe your dates chooses Dan Bilzerian, Leonardo DiCaprio, and 2012 Johnny Manziel – I see you. Go on with your bad self.

Don’t launch into a game of “21 questions” and overwhelm your date with all of the above. Pepper a few uncharacteristic questions into appropriate or slow points of conversation. Whatever you do, don’t be the only person speaking – or you may not have a second or third date. Ask follow up questions and share applicable anecdotes, but make it a point to listen and show interest. If your date was utterly boresome, now you know; pick ‘em better next time. Go get ‘em, tiger.

You may also like

Leave a Comment