This post was published by Taylor Magazine at the following link: http://taylormagazine.com/21-questions-go-deeper-first-dates/.


First dates can be nerve-racking. We want to be ‘double take’-worthy, but we don’t want to look like we tried too hard. We don’t want so late our date thinks we’ve stood him up, but we don’t want to seem too eager either. We want to have enjoyable conversation. We don’t want to offend our date, but, at the same time, we don’t want to pretend to be someone we’re not. We want our date to like us for who we are—not some constructed illusion.

Some topics are typically a good idea to avoid on the first few dates with a new romantic prospect—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.”

We want conversation on our dates to flow naturally, but that’s not always the case. The reality is that some conversations will hit dead ends, because we may not know much about the person or his/her interests and thus run out of relevant comments or questions.

Let’s face it: Some questions are a little bit more boring or pointless than others, when we are trying to get to know someone’s personality and values. Do you like skim, 2%, or whole milk? If a relationship develops, we’ll eventually garner that sort of information. On our first few dates, we’re seeing if this person continues to intrigue us and we’re effectively gauging potential compatibility. We don’t want conversation to mirror that of other first dates. That’s what got us where we are.

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 atypical, but that’s the point—to give you a unique glimpse into your romantic prospect. Happy dating.

  1. If you could be cast 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 walk in Khloe Kardashian’s shoes? Does he want to live vicariously through Harvey Specter from Suits? Maybe she’s intrigued by mysteries and challenges and would opt for Criminal Minds. 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. The Doobie Brothers, J Cole, and Cherub—Your date is definitely not set on one genre. Very cool. 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 favorite 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 his or her 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? Or does she seem like she’s holding back revealing her dreams to you so soon?
  6. What are your favorite 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 considered such a thing 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 mom. He has the occasional planned “family night”—dinner, movies, and games. Maybe there’s very little familial communication but 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, 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 favorite 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 favorite 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 like everybody else.
  17. If you had unlimited traveling 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 wanderlust. You could go on and on about the international destinations to which you’d like to return or experience for the first time… I could use a travel buddy. Do you dislike traveling or have you simply not done much of it?
  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 favorite 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 ole throwbacks? Rocket Power made him take up skateboarding and dream of the living on a coast. The Powderpuff 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 agree on Jumanji and Jurassic Park.
  20. What’s the “craziest” thing you’ve ever done?
    With this question, you’ll only get as far as your date is willing to go. She’s always been extremely organized, became overly obsessive, and finally stopped labeling her office supplies… Crazy. Perhaps your date is on the more conservative side and considers moving away from home for college to be his ballsiest move yet. She went streaking through campus with her senior class. He got a tattoo of his crazy ex-girlfriend’s name. She joined the Mile High Club. He partied with Wiz Khalifa in New York and woke up in Las Vegas. See what your date will fess up to—or laugh hysterically telling you about. Asking about “crazy” experiences will shake the conversation up a little bit. Keep it interesting. You get the point.
  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.

Bonus Question: Why? You can ask “why” to most of the aforementioned questions to gain greater insight into your date.

Don’t launch into a game of “21 questions” and overwhelm your date. Pepper a few atypical questions into appropriate or slow points of conversation. Whatever you do, don’t be the only person speaking throughout the date’s entirety—or you may not have a second or third one. 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.

Advertisements