I met my husband the same way I met lots of guys – while working in a men’s clothing store. Of course, I didn’t end up marrying (or even dating!) any of my other customers. Just Ivan.
So, what made my husband so special? When he visited the store, we had long, fun conversations. We were instantly friends.
By the time he finally asked me out, I felt like I knew him pretty well. Sure, we’d only had three or four short-ish conversations, but in that time we asked each other a lot of questions that dove deep. He asked me if I saw marriage in my future and whether I wanted kids. I asked him the role family played in his life, and what he did when he wasn’t at work.
Fourteen years and three kids later, we still love to just hang out and talk.
While not everyone will have the opportunity to get to know their date in such a low-pressure environment, our love story shows just how important it is to ask the right questions on a date. If one of us had answered those questions in ways that didn’t reflect shared values, we probably would never have gone out in the first place.
With that in mind, I reached out to Neely Steinberg, founder of The Love TREP, a multi-service dating coaching company, to learn more about how to ask questions on a date without making it feel like a job interview. She told me that while getting to know someone should be light and fun, it’s important to go deeper.
After all, if you’re not going to size each other up as future partners, what are you really doing there?
Is there a future here?Unsplash.com
According to Steinberg, it’s important to watch for openings in conversation where you can ask your date something meaningful. Not just the usual questions about family and pets, but also who they are and what they want out of life.
“For example,” Steinberg explains, “if he’s talking fondly about his nephews, that might be an opening to say something like, ‘Sounds like you love kids?’ giving you an opportunity to see what he reveals about this topic.”
In order to know which questions are the most important for you to ask, consider your values. Do you want kids? How important is commitment to you? To ask the right questions of your date, you’ll have to ask them of yourself, first.
With all that in mind, I’ve compiled some of the most important questions to ask on a first date. Remember, there are no wrong answers – just answers that don’t line up with what you are looking for. And like Steinberg suggested above, seize opportunities to ask follow-up questions.
1. What’s on your Netflix list?
This is a fun question, so it’s a great place to start. But this conversation is about a lot more than speculating what will happen on the next season of Stranger Things.
We are truly in a new golden age of entertainment; television is better than ever, with more options than we could’ve imagined. That means there’s a lot to learn about someone by what they choose to watch, and whether your tastes align.
For instance, if serious documentaries are your thing, will you be cool if the person you are in a relationship with just wants to watch reruns of Saved By The Bell? Neither choice is “right” or better than the other, you just want to be sure that your tastes have some overlap.
Even more importantly, if you’re a total couch potato who loves to binge watch on the weekends, you might run into problems dating someone who spends their weekends camping or hiking, and hasn’t watched any TV in years.
2. How do you like to spend a three-day weekend at home?
Would you have friends over every night or do you like to chill alone? Do you dream of a weekend painting your bedroom, or would you rather hire someone else to do that while you go shopping?
How we like to rest says a lot about us. You don’t want to spend your entire relationship fighting about what it means to relax.
At the very least, you have to be comfortable letting someone else recharge in the way that’s meaningful to them while you do your own thing.
3. Do you see kids in your future?
Is a “mini me” part of your future?image.freepik.com
As uncomfortable as this may be to ask, the need for it should be obvious. Becoming a parent is the biggest decision you’ll ever make, and you can’t assume someone else feels the same way you do about it. Talk about it right away. If you know you definitely don’t want kids, but your date says they definitely do, then wrap it up.
You can finish your meal and have a nice chat, but then move on.
4. When you have kids, will you raise them the way your parents raised you?
If you and your date both want to have kids, this question can tell you a lot about who they are and give you a ton of insight into their childhood.
You’ll be surprised the depth of answers you can get out of this one simple question.
5. Do you keep in touch with your childhood friends?
There are no wrong answers here, as this question is more of a conversation-starter.
For some people, maintaining lifelong friendships is a good sign – they value commitment and deep relationships. But for others, leaving the past behind might have been the healthiest choice.
You can’t know until you ask, but learning about your date’s friends can tell you a lot about who they are.
6. How do you feel about booze and drugs?
Bottoms up or thumbs down?https://www.rd.com
This is another area where your date’s answers may be a deal breaker. If you don’t drink at all, you probably won’t be spending your life with someone who does keg stands on the weekend.
And if you love wine with dinner every night and spend vacations touring breweries, you’ll most likely face challenges if your date is sober. No judgment upon either of you, you just might not be a good match.
7. How important are politics and activism in your life?
This question goes a little deeper than, “Who did you vote for?” which can be an awkward icebreaker and lead to a lot of confusion.
Asking what role politics and activism play in someone’s life not only clues you into their political perspective, but will let you know right away whether your commitment levels match.
8. What would you do if you fell on seriously hard times, financially?
My grandmother used to say that money and religion should never be discussed at the dinner table, and it’s obviously very rude to ask how much someone makes or if their family is wealthy. These questions won’t tell you much about your date, anyway.
What’s much more important is how your date would handle big money problems, should they arise. After all, most families will face financial hardship at some point, and nearly every couple fights about money, so it’s good to know whether you values about money are going to align.
9. What are you looking for in a relationship?
Sealed with a kiss d2v9y0dukr6mq2.cloudfront.net
This question cuts straight to the point. That’s why it’s probably the most important question of the bunch. As Nate Bagley, a relationship educator at The First 7 Years asks, “If you don’t share the same endgame, why even bother?”
Bagley has seen the same situation play out time and again, often with heartbreaking consequences. People don’t want to ask the heavy questions, probably afraid that their date will think they’re too serious or rushing things.
But what if the person you’re out with is looking for something light and casual, and you’re looking for a real relationship – maybe even marriage someday?
“Six months down the road,” Bagley explains, “you may realize you aren’t in the same place and you don’t share the same goals. But you love them, and you’ve already invested six months. So you decide to wait and see if they change their mind.”
Skip ahead and it’s two years later, you’ve invested all your time and emotional energy, and it becomes clear that the person you love simply doesn’t want what you want, on the same timeline that you do.
Bagley says, “All of that could have been avoided with one simple question: ‘What is it you’re looking for in a relationship?'”
Some of these questions will show you how different the two of you are, and that can be OK. After all, you don’t want to marry your doppelganger!
But by piecing together everything you’ve learned about someone by asking first date questions like these, you’ll feel like you know who they are and what they want right off the bat, so you don’t have to waste time discovering that you were never meant to be in the first place.
