5 Questions To Ask Your Next Date
“The worst date I’ve ever been on post-divorce felt like I was interviewing for a job that I wasn’t even sure I wanted yet.” - Me
Don’t make the date feel like an interview. We’ve all heard it before, but what does that even mean?
We get to know someone new by asking questions.
We ask questions because how else will we know if we’re compatible or not?
We don’t want to be wasting our time after all…
As a dating coach and matchmaker for divorcées, I tell my clients the goal of a first date is not to evaluate if this person is your future spouse. The goal of a first date is to actually see if you want to go out on a second date, then a third, and so on…
So, how do I learn more about my date without it turning into an interrogation of compatibility? By asking open-ended questions you allow people to discuss topics they feel passionate about!
Passion matters in dating.
Successful dates are ones where you see people’s personalities shine through. On your next first date, forget the “so tell me about yourself” question and get to know your new potential love interest by asking these 5 questions….
1. What’s your favorite thing about this city?
Why ask this? It’s an unassuming but relatable subject. Your date’s response allows you to understand how they feel about the place where you both live and you might just learn a thing or two. Pay attention to how they respond to see if they lead with positivity or negativity in their response.
2. What was the most embarrassing thing you binge-watched in the last 2 years?
Why ask this? Remember in the pit of COVID when you found yourself in sweatpants watching something you never found before *cough cough* Tiger King? This question allows you to see if you have similar taste in programs and to poke fun at each other.
3. Did you go to school for what you are doing now?
Why ask this? I like this for a first date because it's a more layered version of “what do you do for work?” Additionally, it works as a two-for-one question. You find out your date’s job (in further detail than what a dating app title says) as well as better understand their educational background, interests, etc..
4. Tell me about your worst/funniest date…
Why ask this? Life is messy. Dating after a divorce is exceptionally messy. Taking a step back to share a “no way did that really happen?!” story allows you to relate (and hopefully laugh) about something you and this relative stranger have in common — dating. *Disclaimer* Do not lead with this question! It should be used towards the middle/end of a first date.
5. Where’s the next place you want to vacation?
Why ask this? Their answer gives you a glimpse into how they travel and their lifestyle. One of the questions I ask when matching clients is what type of vacation they take. Are you a more all-inclusive luxury resort person or do you prefer to stay in an Airbnb and do as the locals do? You can follow this question up with. “What kind of things would you like to do when you get there?”
Make sure you take some mental notes on all of their responses because it might help you pick out future activities or locations for dates with this person.
A few more fun ones…
What was your AOL Instant Messenger screen name growing up?
What’s the most spontaneous thing you’ve ever done?
What’s at the top of your bucket list right now?
What’s your go-to karaoke song?
Questions to avoid:
How did you vote in the midterm election?
Do you believe in God?
When/why did your last relationship/marriage end?
What’s your body count? (This includes the number of dates you’ve been on since becoming single, as well as the number of people you’ve been intimate with.)
The harsh reality is that if you are continuously going on boring dates, YOU are the only common denominator. Use this next date as an opportunity to try something new.
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