Boomers: What to ask on a date…

By Dr. Gilda Carle, Ph.D.

When you’re single and at midlife, there are those moments when you may believe the lyrics of Reba McIntyre’s song, “Love Is A Hard, Hard Road.” But much of the heartache that could crop up later in a romance might be avoided if only people asked the right questions on their first few dates. Insightful questions at the beginning of a romance can lead to lasting love later. And just because you’ve been at the dating game for a while now doesn’t mean you know all the tricks.

So let me help: To ask the right dating questions, change your mindset to that of a journalist. Journalists gather information, listen intently, remember key facts, and note behavioral patterns. The most effective journalists follow the advice of this Gilda-Gram: “Understand the equation of two ears to one mouth.” What this means is to really get to know someone, listen twice as much as you speak. Down the road, there will always be time to reveal more about yourself. At the very early stages, however, your objectives should be to assess compatibility and determine if you want to go further.


So on your first few dates, favor your observational skills over your making-conversation skills (well-honed as they may be from years of practice). Observation involves walking the tightrope of asking questions without sounding like you’re probing your date’s personnel file. Here, what to ask and what not to ask:

Question #1
Do ask: “What were the good things about your last relationship?”
Do not ask: “What went wrong?”

By asking the first version, you guide your date to pinpoint his or her learning and growth from the past. If your date admits that he or she blossomed, despite the relationship’s derailment, there is a chance that you will be able to grow together yourselves. On the other hand, if your date can’t fathom anything positive about his or her past, this person lacks awareness about the growth factors of life. Regina, 53, asked the “What went wrong?” question and ended up hearing a whole night of “poor me” stories from Bob, 61. This was a real turn-off, and Regina ended their possible future at once.

Question #2
Do ask: “What is your favorite time of day, month of year, climate, and activity?”
Do not ask: “So do you play tennis?” or “Are you a night person?”

Such close-ended questions require just a one-word answer and close down communication at once. Open-ended questions do a much better job of getting the conversation going. Moreover, these might prompt your date to respond with whatever he or she thinks will make the best impression. Pam, 48, asked Pete, 51, if he liked to ride horses. Wanting to seem like a macho cowboy, he said, “Of course!” Little did he expect her to set up a group activity with a few friends at a dude ranch. She discovered that Pete was actually terrified of the four-legged creatures. Pam’s assessment of the guy was that he was full of manure—and she chose not to see him again.

Question #3
Do ask: “What was one of your biggest work challenges, and how did you get through it?”
Do not ask: “Why did you leave your last job?” because you’re likely to wind up wading through all kinds of hindsight and rationalizations.

Asking about a big work challenge will give your date the opportunity to shine, which builds confidence. If your date can pump up his or her skills for you, this person is probably successful in life. Successful people have take-charge personalities that can navigate snarky waters and difficult situations in general. Consider the case of Paul, 58, and Marcia, 59. Paul asked Marcia this question and she spoke about how she managed and supported her staff through a difficult ownership transition that involved a couple of rounds of layoffs. From what Marcia shared, it was clear to Paul that she didn’t get swept up in the drama, but was able to balance the personal and professional challenges of the situation. That was very impressive to him, and he concluded that if Marcia was an accomplished navigator during such challenging circumstances, she would probably be a very level-headed, non-game-playing person to forge a relationship with (and he was right!).

Question #4
Do ask: “Who are your favorite people in your life?”
Do not ask: “Do you like X political figure, or Y religion?” unless you want to engage in rhetorical combat.

When you ask about important people in your date’s life, the response will reflect your date’s true values. Find out about your date's favorite people and why they are being held in such high esteem. Jane, 52, asked this question of David, also 52, and found out that he treasured the friendship of his college pal Michael, who changed careers from finance to social work. David admired his friend’s selflessness and ability to reinvent himself at midlife. That conversation revealed quite a lot of very positive attributes to Jane.

Talking about politics, religion, or any other potentially polarizing topic is, however, best avoided early on. I know, I know: Some single people at midlife consider this kind of question an acid test — either this person will click with me on the tough stuff or not — but I say to hold off. Give yourself and your date a chance to get to know one another first, let the first-date nerves wear off, and then tackle the difficult topics.

Question #5
Do ask: “If you were to describe yourself as an animal, which one would you choose?”
Do not ask: “What is your philosophy of life?” because you’ll only hear what your date wants you to, like all the Miss Americas who vow they want “world peace.”

I have asked Question #5 in workshops for business executives and single people alike. It’s shocking how much information the response to this question reveals. One man described himself as a bear that hibernates during the winter. He was a withdrawn, very low-energy personality—and quite frankly, not much fun to be around. By contrast, a woman once replied that she liked to think of herself as a gazelle—and indeed, she did have a spunky, sparky, and energetic personality which was energizing to be around. A person’s choice of animal says a great deal about who that person is, without the need for a lengthy resume. Now, the question about philosophy — while it may sound sophisticated and likely to yield interesting insights — really will only get a superficial answer in most cases. No matter how much experience a person may have under his or her belt, encapsulating one’s knowledge on a first date is one very tough challenge!

If boomers ask the right questions at the first blush of romantic possibility, their next time around could avoid the relationship issues they attracted in the past. Have fun with these questions! They could offer you greater wisdom than you ever had.

Relationship expert Dr. Gilda Carle, Ph.D., has a private practice and is an associate professor at Mercy College in New York. Her best-selling books include 99 Prescriptions for Fidelity and How to Win When Your Mate Cheats. Please visit her website or send your relationship questions to her at DrGilda@DrGilda.com.