15 Great First Date Questions

There they sit—you could spot them a mile away. A man and woman face each other across a table at a downtown bistro, looking nervous and awkward. No doubt about it, they’re on their first date.

How do we know it’s their first time out together? All the observable and obvious clues: They are nicely groomed and wearing freshly pressed clothes—stylish, but not overdone. There is a stiff formality to the way they sit—no slouching. They scan the room, menu, and table setting, only occasionally making eye contact.

Biggest clue of all: The salad course is punctuated by strained silence and forced small talk. The two pick at their dinner salads, staring down at the leafy mound before them. He seems tongue-tied, she seems self-conscious. Finally, one of them tries to grease the wheels of conversation.

Him: How’s your salad?
Her: Good. And yours?
Him: Yeah, really good.

More excruciating silence ensues. You can almost read their minds. He thinks, “C’mon, say something! Anything! This is torture.” She thinks, “Why doesn’t he ask me any questions? Or maybe I should—but I don’t know what to say! How can I get out of this?”
On it goes. More mute lulls. More perfunctory questions. More salad staring.

As would-be romances go, this plane is very slow to leave the gate and get onto the runway. It remains to be seen if it will pick up speed, gain altitude, and soar skyward . . . or if it will lose engine power and sit on the tarmac indefinitely.

Singles: do not let this happen to you! It’s true that first dates can be one of the most nerve-wracking, anxiety-producing situations in our society. Sometimes they lead to burning love; sometimes they go down in flames. The key to having a positive experience is relaxed conversation, and that can be helped along with some well-chosen first-date questions. Before we get to those, let’s review a few general guidelines for dating discourse:

Listen as much or more than you talk. Some people consider themselves skilled communicators because they can talk endlessly. But the ability to speak is only one part of the equation—and not the most important part. The best communication occurs with an even and equal exchange between two people. Think of conversation as a tennis match in which the players lob the ball back and forth. Each person gets a turn—and no one hogs the ball.

Peel the onion, don’t stab it with a paring knife. Getting to know someone new is like peeling an onion one thin layer at the time. It’s a slow and safe process. But some people, overeager to get into deep and meaningful conversation, go too far too fast. They ask personal or sensitive questions that put the other person on the defensive. Should the relationship evolve, there will be plenty of time to get into weighty topics. For now, take it easy.

Don’t dump. If feeling inhibited is a problem for some people, others go to the opposite extreme: they use a date as an opportunity to purge and vent. When a person reveals too much too soon, it can give a false sense of intimacy. In reality, premature or exaggerated revelations are due more to boundary issues, unresolved pain, or self-centeredness than true intimacy.

Genuine interest goes a long way. Maybe your first date questions will lead you to discover that this person is your soul mate—or maybe not. Either way, it’s exciting to be able to get to know another human being and get a peek into his or her world. Great communication starts with being genuinely interested in the individual you’re with and paying close attention to what he/she says. The process begins by providing lots of space for the full expression of information and asking follow-up questions to further draw out the one talking.

With those thoughts in mind, now it’s time to think about specific first date questions.

Try these:

1. Who has been the biggest influence in your life?
2. What kinds of things really make you laugh?
3. What’s your favorite place in the entire world?
4. Who is your best friend? What do you like about him/her?
5. Favorite movie of all time? Why so?
6. What’s your biggest goal in life right now?
7. What is your favorite way to spend a Saturday?
8. Do you have any pet peeves?
9. What was your family like growing up?
10. What were you like as a kid?
11. What should I know about you that I’d never think to ask about?
12. Did you—or do you—have a nickname? What’s the story behind it?
13. Who was your favorite schoolteacher or college professor? Why?
14. Have you figured out your calling in life? What is it?
15. What do you hate most about the dating process? (Tell me so I can avoid it!)

Maybe you’ve got your own great first date questions, surefire winners that get the conversation rolling. If not, use these and come up with others—but by all means, give some forethought to how you’d like a discussion with a new partner to unfold. You’ll give yourself a chance at a magnificent, rather than miserable, first date.