I have a new client, Sandy. She lives in San Francisco, she’s in her mid-60s, and she hasn’t dated in over 30 years, since before she was with her late husband. Dating has changed a lot since then.

She and I had a few pep talks about first dates — what to wear, where to meet, who should pay, and how to end a date depending on how it goes. She sent me a follow-up question before her first first date in a long time, asking:

“Should you ask about their job (what exactly does your job entail?), where do you live, tell me about your children, and how do you tactfully ask about exes or deceased spouses?”

My response was simple:

“I would actually avoid most of those topics for a first date. They can end up being really serious (and the job one might feel more like a networking session) and don't necessarily really help you get to know someone in the present. Just see if you get along, laugh, have rapport, and then the deeper stuff will come out in time when you are both comfortable.”

Now, I’m not saying that you can’t talk about your work, of course, especially if it’s a big part of your life. Same with children. What I am saying, however, is that if you’re asking these questions to try to assess something about this person based on a simple answer to a complex question (like how much they make or how much time they have to devote to dating), then you might be doing yourself a disservice.

For example, let’s say that someone’s ex-spouse was abusive in some way. Now, asking your date about a divorce might bring up some unsavory feelings, ones that revealing on a first date would be entirely premature and perhaps triggering.

First dates should not be paired with telling your life story. They should instead be about revealing who you are today. If you have children, of course you can share some tidbits, but not at the expense of your date learning about you.

I remember once a long, long time ago, a date asked me, “So tell me about your last relationship.” That was not something I wanted to share at that time to a complete stranger — it was personal. So, I deflected, saying that I didn’t want to bring someone else into our date since I was just getting to know him. (This is something I recommend saying.)

But he wouldn’t relent!

Finally, I said, “You know, I spent years in therapy getting me through that period of my life… that’s the last thing I want to talk about now!” That stopped him in his tracks, and I didn’t really care if my abrasiveness turned him off. His nosiness turned me off. I have no doubt he was trying to assess something about my last relationship. But the reality is than many of us learn and grow and become better for the next relationship. And every relationship is different, so to learn about one doesn’t predict the course of the next one.

In the end, my client Sandy went on that first date. She said it went OK. No sparks flying, but not a negative time. And they talked about what they enjoy doing during the day, not the deep stuff that will never be relevant because they don’t plan to see each other again.

Keep in mind, though, that if these topics come up, I’m not ever going to admonish you or say you did something “wrong.” Every date is different, and some inspire us to share. There’s no one-size-fits-all solution. But I recommend not going into a date looking to learn everything about someone’s past. Let’s leave it just there… at least for now. And get to know who someone is today.

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