Ask Wendy

What Questions Do I Ask on a Date?

Friday, September 2, 2016
couple on a date
Hey Wendy,

What would be some key questions to ask in the dating process to find out if he is the one?

Regina W. — Palo Alto, CA

Hey Regina,

Good thing you said “dating process” I know you don’t mean when you first start dating, right? If you’re referring to the first few dates, skim the last column. Your job is to get to know this new person, don’t try to vet him too hard.

The things you hope to learn about a guy vying for “one” status won’t come from asking questions. The elements that make him the right person for you will show up over time, when he has a track record with you. Here’s what I think you need to know:

  • Does he like me
  • Will he call me and have follow through?
  • Is he kind to animals, children and service people?
  • Is he financially responsible?
  • Will we have peace in our relationship because we share core values?
  • Is his emotional intelligence a match with mine?
  • How are we at solving problems together?
  • Does he see the real me?
  • Can he comfort me?
  • Does he empower me?
  • Will he bring out my best self or will he stifle me?
  • Does he have my back?
  • Does he have staying power?

You can’t ask any of those questions when you’re out having dinner on a date anyway. Well, you could, and I’d like to be a fly on the wall of The Shake Shack when you tried.

Start by talking about what matters to you to see if you share similar values. See if you can get an “oh, me too!” out of him. And (optimally before you sleep with him) definitely whip out your deal-breakers so you’re not wasting each other’s time.

Some of the most important information you can learn about a date comes from watching them. Pay attention to his level of interest. Is he only responding when you reach out or is he generating dates and sexy/flirty “I like you” connections with you? How long does it take him to set something up with you? How often is he cancelling? Is he tentative to lock the next date down? Is he paying enough attention to you? Because you, my love, are worthy of affection and attention from your “one”.


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