Stop Interviewing Your Dates - Please
This happens so often and it backfires on so many terrific people who are keen to find their partner. Often I wonder what happened to having fun with your date? Let’s shift the perspective - if you are interviewing your date, then there’s immediately a feeling of inbalance. One person is judging if another is worthy. That is not what relationship building is all about. And it backfires.
Is the goal to build a relationship built on mutual interest, joy, and lifelong learning together or is it to check boxes? Moreover, often I’m not sure people are really asking all the right questions either. It’s typically very basic about ambition, family plans, career, etc. And very little about what makes them laugh, about their parents, about why having kids can be a way to relive life and be a kid again and what would be totally fun to do? Or even what is a favorite childhood food? That seems to be a lot more than an interview checklist.
So, my friends - If your first dates feel flat, it might be because you are asking résumé questions: What do you do? Where did you study? What are your hobbies? Efficient at getting basic information—but often getting back pretty canned responses. And if your date has been dating already, these are the same questions they are already being asked.
Stir up the conversation and start asking “what” questions, avoid the why. I shared this at a recent corporate talk that I did about networking for a venerable corporation - sharing tips from a matchmaker, that is also useful in the business world. What questions can lead to more explanation. Why questions can inadvertently come across as judgemental.
Thank you for choosing this Italian restaurant - what would you order if you could try 3 things? What desserts look the best to you. (Don’t ask why did you choose the chocolate lava cake, well, ok - you can)
You like hiking? → What do you actually love most about it? The scenery or how you feel when you’re done?
Into wine? → What wine was the first one that you really enjoyed?
This does two things fast.
1) It helps to get your a real connection. "What" can help pull people out of those boring rehearsed scripts and into a thoughtful responses. Skip the bullet points.
2) You get a real answer. Anyone can list hiking, wine tasting, a list of cities traveled to. If you want a solid relationship then you want to really know someone - you will be living together!
Nobody enjoys being grilled on the spot especially by a potential partner - but people love it when someone takes an actual interest in hearing them without judgement!
Try it out - ask better questions and I know that you will get better answers.
📊 And the research backs this up - Research by psychologist Arthur Aron and colleagues, later replicated across multiple settings, found that pairs who ask escalating "what"-type questions—moving from surface facts to personal meaning—develop measurably stronger feelings of closeness than those who exchange factual information alone, even in a single conversation. (Aron et al. – The Experimental Generation of Interpersonal Closeness)
Interested in some actionable first-date tips tailored to where you live? Browse ourSan Francisco dating guide and New York dating guidefor venue ideas and conversation starters suited to each city's dating culture. Or let’s work together Ancient Wisdom Modern Love's coachingcan help you show up as your best self on every date.
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