The best first dates are relaxed, enjoyable times to get acquainted with someone new. No one wants a first time out to be filled with pressure and anxiety. Plenty of singles complain, “The date felt like a job interview!” Or, “I got the feeling I was being interrogated.” (
It’s true also that one of the primary goals of a date is discover important things about the other person so you can evaluate if you want a second date (or even a third!).
As naturally and casually as you can work them into conversation (rephrased in your own words of course), here are eight first-date questions you should ask, since the responses will reveal significant things about the other person:
1. “Where did you grow up, and what was your family like?” The eminent psychologist Karl Menninger said that one of the most reliable gauges of a person’s emotional health as an adult was a stable, satisfying childhood. This doesn’t mean, of course, that you should automatically avoid someone who had a difficult upbringing. But you do want the assurance that the individual has insight into his or her family background and has sought to address lingering wounds and unhealthy patterns.
2. What makes you laugh most? A good sense of humor appears on virtually every study of “what singles want in a partner.” But of course, not everyone finds the same things funny. Some people laugh at humor that others find rude. Others are turned off by “sophomoric” humor and are drawn to sophisticated, ironic humor. Some appreciate putdowns and sarcasm, while others want their humor clean and gentle. The point is, what a person finds most funny says a lot about his or her personality and perspective on life.
3. “What’s your big passion?” This gets to the core of a person’s being. If the individual responds with “I dunno,” that might be a red flag that he or she isn’t passionate about anything. But you’re likely to get valuable insight from the person who answers, “My kids … Travel … My church … My career … The mentoring program I’m involved with … Rock-climbing …” Follow up with questions about why the person become so passionate about this particular endeavor or emphasis.
4. “What are you looking for in a relationship?” This may strike some as too pointed—like you’re trying to determine if you fulfill the job description. But it is helpful to know right up front if someone responds, “Fun and companionship. I’m not interested in anything serious right now.” It’s also helpful information if someone says, “I’m looking for someone who shares my values and wants to explore a future together.”
5. “Is there something you’re working toward right now?” This isn’t exactly a “trick question,” but the point is to assess if the person has ambition and motivation. It’s probably a sign of complacency or apathy if your date replies, “Goals? No, not really.” But if that person has a goal he/she is working hard to achieve, that indicates drive and determination.
6. “What do your Saturdays usually look like?” How discretionary time is used says a lot about a person. If she works on her “day off,” she might be highly career-oriented…or maybe a workaholic. If he spends the day coaching a kids’ soccer team, it’s a good bet he loves sports, enjoys kids, and wants to help others excel. If he watches TV and plays video games all day, you may have a couch potato on your hands.
7. “Who are the most important people in your life?” Your date might answer, “My parents” or “My college roommate” or “My kids.” In addition to understanding the other person better, this question allows you to assess his or her ability to form close relationships.
8. “What’s your dream?” You’ve asked about the person’s goals, which tend to be short-term and narrowly focused. Dreams, on the other hand, are usually grand in scope and vision. You probably 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. If your dating partner’s highest dreams involve owning a Malibu beach house and driving a Ferrari while yours involve serving starving children in Africa, that’s going to be a problem. Listen closely to discern if your dreams are compatible and complementary.
What are your “go-to” first date questions?