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The Best First Date Questions for Seniors

By eHarmony Staff

senior dating tips first date questions

Regardless of a person’s age, first dates can be a source of anxiety and apprehension. You may not be the bundle of quivering nerves you were as a teenager going out with someone for the first time, but even as a senior you want to avoid awkward silences and gaps in the conversation that leave both people feeling uncomfortable. Most of all, you want your time with someone new to be an enjoyable, fun time of getting acquainted.

You may have your own tried-and-true questions to foster conversation, but if you need fresh ideas, try these …

“What’s the most interesting job you’ve ever had?” By the time people qualify for “senior” status, they’ve likely held down several, if not many, different jobs. Chances are, your date will have at least one unusual or intriguing job to tell you about. Which will give you a chance to share about your own most fascinating work experience.

“Do you have a special place you like to visit regularly?” We’ve all got our go-to spots that keep luring us back, whether they are funky coffee shops, scenic hiking trails, or relaxing weekend getaway locales. Your date may have a local park he/she frequents or a European city that’s been a regular destination. Learning where your partner likes to go will provide insight into the person’s tastes and temperament.

“What is the most fulfilling thing you’re currently involved in?” Your date may still be immersed in a career and finding satisfaction in it. Or it may be a volunteer position that is most rewarding. Relationships with grown kids or grandkids could be the biggest source of fulfillment. Whatever answer you receive will provide plenty of opportunities for follow-up questions.

“What are you most passionate about at this point in your life?” The things that motivate and inspire us change at various stages of life. So you might also ask how the person’s passionate pursuits have shifted over the years.

“Who are the most important people in your life?” Your date might answer, “My kids” or “My friends” or “My bridge club.” In addition to understanding the other person better, this question allows you to assess what he or she values in close relationships.

“What makes you laugh?” In virtually every study of “what singles want in a partner,” a good sense of humor ranks high. No matter the season of life they’re in, single men and women want a partner who can bring levity and lightness to the relationship. Discovering the kinds of things that make your partner laugh will tell you about his/her personality and outlook on life—and help you introduce those laugh-inducing elements into your times together.

“Do you have a dream you’re pursuing?” Dreams and lofty ambitions are not the exclusive domain of people in their twenties and thirties. At every stage of life, dreams should be nurtured, cultivated, and acted on. Hopefully, you have dreams for your future, whether they involve career achievement, world travel, volunteerism, or artistic expression. You want to know if the other person’s dreams mesh with your own. Listen closely to discern if your dreams are compatible and complementary.

Do you have a go-to, surefire first-date question?

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