The 10 Dating Questions Every Woman Should Ask on the First Hang, According to a Relationship Coach

first date

“Hello there, New Person. Please fill out this three-page suitability spreadsheet, and I’ll let you know if I'm free for a second date.”

Ah. If only. But how can you low-key figure out if a person is right for you from the get-go? We asked relationship coach Jocelyn Johnson for guidance on what questions to ask—and behaviors to look for in—your maybe-lover. In early dating, there are four things you want to figure out about the person. According to Johnson, these are “Values, interests/lifestyle, level of integrity/commitment and how they manage conflict/hardship.” Here’s how to find out all this info with ten easy dating questions.

1. What sort of relationship are you interested in?

Ask it straight out, Johnson suggests. Right from the beginning, you’re going to avoid the hurt feelings and misunderstandings if one of you is looking for a casual hook-up and someone else wants marriage material.

2. What are the ideal qualities you want in a partner?

After they answer this, ask a few more questions about a couple of the qualities—like did they ever have that in a relationship before. And note if they listed both superficial and substantial qualities. For example, a great smile and a kind spirit might be answers, but notice how the second quality is super vague. “‘What does a kind spirit mean exactly?’ could be a good follow up,” instructs Johnson.

3. What's a typical work week look like? And what about a typical Saturday?

If you're a social butterfly, you're not going to be happy with a couch potato. Or vice versa.

4. What's your family like?

“Understanding how they relate to their parents and siblings, if any, is important,” Johnson says.

5. What was a challenging time recently and how did you handle it?

Johnson says that listening for your date’s account of how they did or did not have a support system and their narrative of resilience is going to give you a window into their personality.

6. So, I was just listening to a news story about [insert controversial news topic here]. What're your feelings about that situation?

“Ask at least one comfort-zone-breaking question,” Johnson suggested. “This is a chance to see if this person will be radically honest with you and stay true to him- or herself versus saying what they think you want to hear.” Additionally, it’s a way to see if you are both share similar levels of political and popular culture engagement.

7. When was your last relationship? And why did it end?

“Remember that there are three sides to every story, so listen closely—does the person pass blame or take responsibility equally?” Johnson said. “Was it an amicable split? If not, how did they handle the ending? Their answer tells you a lot to how they will handle conflict with you.”

8. What was your longest relationship? What made it last so long? Why did that one end?

See number 7.

9. How often did you and your prior partner hang out/spend time apart?

You want to make sure you both have similar expectations of couples’ and private time.

10. Now, observe, then ask yourself—Does your date “walk the walk” with these behaviors?

• Are they present and attentive?

“Is this person looking around? Distracted? Not fully listening to you when you speak?” Johnson asks. “Do they cut in to talk about himself/herself on a related or unrelated point? Does s/he ask follow up questions? Inquire deeper? Show genuine interest/curiosity to understand you?”

• Do they show up and follow through?

It sounds basic, but Johnson says this is a basic barometer of integrity. Do they do what they say they will? If they say they’re going to check up on how your job interview or deadline went, well, did they?

• Do they display general acts of thoughtfulness, compassion and kindness?

“Does he open the door, how does she greet others?” Johnson asks. “In the movie A Bronx Tale, the main character Calogero gets advice from a father-like figure, Sonny, who tells him to watch if the girl he takes out reaches over to unlock the door for him. Sonny says this is the way to tell if she’s thoughtful and not selfish.”

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dana dickey
Dana Dickey

Senior Editor

Dana Dickey is a PureWow Senior Editor, and during more than a decade in digital media, she has scoped out and tested top products and services across the lifestyle space...
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