15 First Date Questions You Can’t Ask

Hey Wendy,

I’ve been flirting with someone online who I really like. What would be some key questions to ask in the dating process to find out if he is the one?

Regina W.

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Hey Regina,

We don’t like it, but the truth is that dating to sort for a relationship is a process, not a twenty-questions deal.

Also: Sorting should not start before meeting IRL — or on date #1.

The Point of a First Date

On your first date, your whole job is to get to know this new, interesting person and show him a bit about who you are as a new, interesting person. That’s it. No checklists, no strategy.

There’s only one question to answer: “Do I want to spend more than ten minutes with this person in my future?”

Initial flirting and the first date are not for vetting.

Now, I’ve been at this awhile, so let me be direct and answer the question underneath your question: Here’s a list of:

The Most Important Questions You Can’t Ask

• Does he like me?
• Will he call me after this date?
• Does he have solid follow-through?
• Is he kind to animals, children, and service people?
• Is he financially responsible?
• Will we find 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 I be the real me around him?
• 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 over burgers and milkshakes at Shake Shack.

Those answers will come when he’s established an honest-to-God, real-world track record with you.

So instead of leading with a checklist, start by talking about what matters to the two of you.

Here are a few questions you can ask back and forth to get things going:

Unusual First Date Questions

• What do you care about?
• Who’s your underdog? (Why?)
• What do you love about your life?
• What’s the first thing you’re going to do when this stupid pandemic lightens up?

Compatibility starts when you can get a couple of “Oh, me too!” responses out of him.

Just How into You is He?

The most important information you can glean from dating comes from watching him.

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 canceling?

Is he paying enough attention to you?

We can only be at our best when we have enough attention and interest from the one(s) we date. Without enough connection, we’re trying to be amazing on top of being off-balance. And that rarely turns out well.

If what you’re after is lasting love, there’s a bunch of things to pay attention to when you’re dating: You’ve got to spot the red flags, celebrate the green ones, and mentally stick pink post-its next to behaviors to check back on. If you want to know exactly what to look for, and how to succeed at dating to find your love, grab my DIY Dating Workshop, Ready for Love.

Good luck out there and happy dating!

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Previously Published on medium

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