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First Date Tips: The Best Questions to Ask a Woman

Avoid awkward conversation lulls and expedite the get-to-know-you process.
First Date Tips: The Best Questions to Ask a Woman

Ah, the first date. Where great relationships begin, or stumble into awkward, dead-end conversation.

The key to creating a solid first date experience is the art of banter, which begins with asking meaningful questions. Great questions, asked well, give you and your date plenty of material to work with—and endless conversations to explore. So, what makes for a great question, as opposed to a dull back-and-forth?

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First, you've got to express genuine interest. More important than the specifics of the question is your intention in asking it. If you don't truly care about the answer, then any question will fall flat. You always want to make them open-ended. Avoiding yes or no questions creates organic conversation, and allows you and your date to really get to know each other. Plus, you can tailor any question to avoid the dreaded one-word answer and keep the conversation going so long as you're aware of your phrasing. And lastly, your questions should blend into conversation naturally, building on the most positive points. Rather than treating questions as a first date script, weave them seamlessly into conversation, by asking, listening, and following up with new topics and further questions. Before you know it, you’ll be using questions to inspire a natural exchange.

With that in mind, here are seven great questions to ask on a first date.

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Very few people ask this question, but it's a great way to get to know someone—especially if you live in a larger city with lots of transplants. You're giving her the opportunity to remember who she was before she got here—and what she liked best about that time in her life—and to share that story with you.

Like all good questions, this one might invite a surprising answer. That is gold for first date conversations. If she happens to have a negative impression of where she grew up, there's a good chance no first date has given her the simple gift of talking about it—or the opportunity to remember the positive aspects of her childhood. Either way, you'll discover a ton of interesting personal detail in the process.

This question also gives you an opportunity to compare your own upbringing. Just like that, you’re connecting on very personal themes and getting vulnerable with a new person.

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Even people who don't travel regularly love talking about travel. Fantasizing about the world is a great bonding exercise, and an excellent way to get to know someone.

If she hasn’t traveled much, ask her where she most wants to go. The places she has traveled as well as the places she wants to travel give you a lot of insight into who she is. A girl who wants to hike Kilimanjaro has very different interests than a girl who wants to stay in every seven-star hotel in the world. Look for the deeper information contained in her responses. Travel is a great shortcut to deeper values and priorities.

Listen carefully and explore her responses to find new sources of conversation—stories from your past, places you’ve both been, and plans you both share. Along the way, you’ll be learning a great deal about your date through a fun conversational mix of experience and fantasy.

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The beauty of this question is it avoids the tired "So what do you do for a living?" that every other date has already asked. It’s open-ended enough that she'll probably mention what she does for a living as part of her answer, while opening up the response to non-work activities. And it guarantees that her response will be more than a one-word answer.

If she doesn't like her job enough to include it as part of the week's "best of,” then you’ve avoided that landmine. It's better to save a common topic for later than remind her of a place she doesn't associate with positive feelings. Remember, a first date should be fun and pleasant—an enjoyable distraction from her everyday routine.

With a question like this, she gets to determine what she wants to share with you about her week, and you get to listen. She's telling what she's most excited about, and that's excellent information for you to decide if this is someone you'd like to spend more time with. It also opens up new avenues of communication based on that positive information.

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If (and only if) she does seem to want to talk about work, this is a great follow up question. It's another question designed to ask something obvious in a surprising way. More than simply asking her to tell you what she does for a living, you're steering her toward the positive aspects of her day-to-day life.

If she likes her job, you'll find out what she's most passionate about. If she doesn't like her job, you'll find out what keeps her going back every day. Both are fascinating topics of conversation, with lots of follow-up to explore.

You can understand a woman's values and priorities by asking her what she likes about where she works. How she spends her professional life will tell you how she feels about money, colleagues, the workplace, and her time. You can then use this question to pivot to more specific questions about her passions, interests, and aspirations.

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While you want to keep your questions positive, this question is a great exception. By asking her to talk about the not-so-fun parts about dating, you're not trying to get her to vent, but to lightheartedly acknowledge that dating can be awkward. You’re also signaling that you’re comfortable talking about her dating life, and that you’re confident that this date won’t go poorly.

When you ask this question, smile big and make sure she takes this as an invitation for lighthearted banter. If she's open to it, this can be a great foray into hilarious stories you two can share about the funny process of dating. It’s important that you share your own dating anecdotes, so she knows that you two have both shared these experiences. If you do that, you can almost guarantee that this date will rise above the others.

Something deeper will also happen here. Opening up about your vulnerabilities is a great way to bond. When you each expose parts of yourself that are a little uncomfortable, you're showing something most people don't get to see. By connecting in this way, you’re accelerating rapport and trust, which are the lifeblood of a new relationship.

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Think of this question as a more targeted way of asking what her childhood was like. Because this question is closed and specific, you'll want to follow up with additional questions, like, "How did you two become so close?" or, “What was it like growing up with three brothers?” These questions will lead into a rich personal history.

The key here is to actively listen and frame her responses ("It sounds like you and your dad spent a lot of time golfing together."), then ask a relevant question that also pivots the conversation a bit ("What about your mom? What did you two do together?") Your responses will require you to think on your feet and come up with solid follow-up questions.

Like the “best part of your week” question, this one gets into common topics without reciting the usual “So tell me about your childhood” line. Done right, this will help you understand where your date came from and what kind of person she is—and allow you to open up to her in response.

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This is a “big” question, but with the right tone and follow-up, it can be a really fun exchange of your deepest passions. This will get to the heart of her interests and values, which is essential information to gather on a first date.

Now, this question could turn into a bucket list conversation, which can be a bit intimidating at times. Still, it's one of those questions everyone wishes someone would ask, but no one ever does. The key is to ask it in a genuinely curious, nonjudgmental way, and be ready for whatever she decides to share.

If the conversation permits—especially if she struggles to answer the question—you should offer your own answer. Share it openly, without pretense, and use it as a jumping-off point for more conversation. It might inspire her to share her goals, or invite her to comment on yours.

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