First dates are exciting, with the potential that, in the words of a pop song from the middle of the last century, “This could be the start of something big.” And — for that very same reason—first dates are also nervous-making. What if this is The One, and you say something wrong to them?
Making conversation with a relative stranger is a challenge for some people, especially those who are not naturally glib conversationalists. And when you don’t know much about the other person’s interests, it’s tough to pick topics that will interest them.
Here are three things to remember:
- Most people would rather talk than listen, especially if they are talking about themselves. So ask questions.
- Don’t ask yes-or-no questions, or other questions that can be answered with one word. Ask open-ended questions instead.
- Unless politics or religion is extremely important to you, and you cannot see yourself paired with someone with differing views, don’t bring these up on a first date. If differing views are a deal-breaker for you, then you may as well find out up front. Otherwise, steer clear of potentially “combustible” topics until the relationship is on a surer footing.
Here are some questions that, with suitable follow-up questions, will keep the conversation going for quite a while. You don’t need to ask them in the order given:
- – If you could do anything at all for a living, what would you want to do or be? (Follow-up questions: Why? How long have you wanted to be a ____? Who or what inspired you?)
- – What’s the best part of the job or career you do have? (Follow-up question: What’s the worst part?)
- – Tell me more about your job/career and what it entails. (Follow-up questions will depend on what your date says.)
- – Who do you most admire in the world, and why? (Follow-up question: Has this person always been your hero?)
- – What was your childhood ambition? (Follow-up questions: When did you change your mind and why—did you just “outgrow it” or what?
- – Where have you lived so far in your lifetime? (Follow-up questions: Which was your favorite, and why? Tell me more about it. Why did you leave there? Do you think about going back to visit some day—or would you rather just remember it the way it was then? If you could live anywhere at all in the world, where would you choose? What made you move to where you live now?)
- – Tell me about some of your friends. Who are your closest friends and what are they like? (Follow-up questions: What do you enjoy doing with your friends? What are the qualities that are most important to you in a friend?)
- – Tell me about your parents. (Follow-up questions: Are they both still alive? Were they strict or lenient when you were growing up? Where do they live now? How often do you see them? Do you have other close relatives—brothers, sisters, grandparents? Where do they live? How often do you see them? What else do you want to tell me about them?)
- – Have you ever been married? (Follow-up questions: How did the marriage end? How long did it last? Do you have any children? What are their names and how old are they? Where do they live? How often do you see them? If you’ve never been married, have you ever been engaged? What happened that you didn’t marry him/her?)
- – What do you like to do for fun?
Bonus question: What else would you like to tell me about yourself? What else would you like me to know about you?
Don’t ask your date any question you aren’t prepared to answer about yourself.
Your date may well answer your questions and then follow up each answer with, “And what about you?your _________.” You can’t refuse to answer a question you’ve just asked them, so if the question is one you don’t want to answer yourself, don’t ask it of your date.
None of the questions suggested above should normally be “booby-trapped.” Nominally they are all safe. But of course, you can’t know your date’s circumstances. An innocent question like “Why did you leave your last job?” can be “loaded” if the answer is “Because my boss raped me” or “Because I was falsely accused of molesting my assistant.” “Do you have any children?” can lead to “I had a son, but he was killed just last year.” There is no way, however, to predict such a circumstance. You have to take your chances.
While you don’t want to monopolize the conversation and talk about yourself all night long, neither do you want your date to think they’ve walked into an inquisition. If your date doesn’t ask you questions in return, it is good to find an opportunity to volunteer something about yourself at some points in the conversation. For example, if your date says, “I love the job I have now!” and then goes silent—so you are not interrupting—that could be your cue to say, “Oh, great! I love my job too. I’m a _______ and I love it because ____” or “ I wish I could say that, but I really don’t enjoy my job. I’m a _____, and it would be okay except for ______,” or “I guess my job is okay, but I really wish I were a ______ instead.”
Other than blowhards and extreme egotists, people don’t normally enjoy monopolizing the conversation. Even if your date enjoys being the center of attention and talking about herself or himself at the time the date is going on, they may have regrets afterward and think, “Oh wow—I really messed up, talking about myself all night long. What must he/she think of me?”
One last bit of advice: Don’t feel you have to stick to the 10 questions above.
They aren’t the 10 Commandments. They aren’t set in stone. Relax and let the conversation go wherever it flows. If you wind up asking other questions or pursuing other avenues of conversation, that’s fine. Save the unasked questions for the next date.
You do hope there will be a next date, don’t you?