First dates are equally exciting and equally nerve wracking. While it's fun putting on lipstick and dabbing on perfume like you're Elizabeth Taylor, the idea of having to spend a couple of hours with a complete stranger could be hella intimidating. And while we have the tried and true questions of "what do you do?" and "do you like dogs?" down-pat, it can be tricky moving the conversation away from awkward small talk. What you need are a couple of questions that'll get them sharing stories and laughing over experiences. So graduate to medium talk with a couple of these fun and chatty questions!
1. Where Do You Live In The City? Why Did You Choose That Neighborhood?
It's pretty telling as to where a person chooses to live in the city – are they in the fraternity district where Jaeger runs like water? In the artsy area where there are more record stores and coffee shops than parking spaces? In the residential district that's more about the big parks and organic grocery stores? Or in the young professionals neighborhood, where there are more blazers in the bar than martini glasses? Obviously you won't be able to peg a person just because of their area code, but it'll give you a small glimpse into their personality.
2. How Did You End Up Choosing Your Job?
This is a great follow up to “what do you do?” because it'll get you a story, not a one word answer. Sometimes we end up on our paths out of circumstance, but that circumstance has a whole origin to it. They just moved to the city and had two weeks to make rent, they got it offered randomly while at a bar, they're doing it to make ends meet but really they want to do this and that one day, or maybe they've wanted to do just what they're doing since they were in the first grade. It'll be fascinating.
3. Have You Traveled Anywhere Cool Lately?
Even if it's just a neighboring town but they found a crazy fusion restaurant they'll never forget, talking about your travelers will get you excited to talk about what you've experienced, who you met, and how you felt being somewhere completely new. If your date responds with something unenthusiastic, take the reigns and prod a little. Ask what kind of people were there, what was the most interesting dish they sampled, did they see any live music, what was the most memorable part of that weekend – anything! Sometimes it just takes a little push to get the ball rolling into a fun conversation.
4. Where Else Would You Like To Live If It Wasn't Here?
Is it in a smaller town by the mountains? In a cozy city like Portland? Or a bigger, more bustling area like San Francisco? Or better yet, would it be an expat situation where they'd hole up in Madrid and hang out in cafes underneath orange trees? Not only will the answer give you a glimpse into their personality and interests, but it'll also open up the floor for more stories. Chances are they've visited that place before, and there was something about it that made them fall in love with it. Learn what exactly that was!
5. Do Your Parents Still Live In The Old Neighborhood?
This will open the door for hilarious childhood memories – one time a guy told me how he wanted to know what it felt like to throw eggs at a house, so he took a carton out of the fridge and egged his own garage. At the very moment his dad pulled up in the drive way. Tears. Tears in my eyes from laughing.
6. Do You Like What You Do In Your Job? What Would You Like To Do Next?
We're all constantly growing and reaching for higher goals, so hearing about what they're trying to build towards next would be interesting. It's always amazing to watch someone talk about something they're ambitious about and hopeful over, and it'll give you the chance to learn something new. Are they a musician and piecing together a tour? A consultant and tired of traveling every other Tuesday? A writer and working on exploring new topics? Just think about where those conversations could go.
7. I Have To Buy My Friend A Birthday Present This Week. What's The Best One You've Ever Gotten?
Was it an X-Box? Tickets to a show? A surprise plane ticket? A painting of his Schnauzer? The answer will be fun, and it'll give you an idea what he holds important.
8. I Can't Wait For The Summer. What Was The Most Fun Thing You Did Last Year?
Did they go to a new city you haven't visited yet? Spent a weekend at a festival? Tried the most amazing food at a neighborhood fest? Went camping in the most unreal mountains? Spent every weekend at a hidden taco joint you haven't heard about yet? There won't be anything but good vibes remembering your favorite moments from July.
9. What's The Most Spontaneous Thing You've Ever Done?
Was it road tripping to New Orleans just for the night, or was it switching over to the organic avocados at the grocery store? Either way, you'll get a good laugh and a great memory.
10. What's The Worst Job You've Ever Had?
Were they the popcorn guy at a movie theater? Did they work for a boss with a Napoleon complex? Did they have a Dwight Schrute in their last office? Let him dish.
11. What's One Thing You Regret Not Doing?
Maybe it was not taking a year off and going traveling, or not going to a college that his parents disapproved of. Maybe it was not trying out for that one job he thought there was no way he'd get, or flaking on a road trip because of money. Whatever it was, it'll be fun and it'll make you two think about how you shouldn't let awesome chances slip away. Wink, wink.
