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10 Questions to Ask on a First Date

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10 Questions to Ask on a First Date

First dates can be awkward or fun, uncomfortable or relaxed. You can meet someone on a first date and never hear from him again. Or you can meet the love of your life. In short, first dates are unpredictable. One way to make them easier is to ask the right questions. Ones that, when answered, should reveal something about your date and your potential compatibility. Don't know where to start. These are the first date questions we highly recommend.

1. Do you have any siblings?

Whether the answer is no siblings or 12, asking this question is a gateway to learning more about your date’s family and personal life. Were they close? Are they still close? What was the parenting like? What difficult experiences did the family go through together? What kind of traits did your date take on as a result of his relationship with his family? You can glean a lot about a person by discovering more about his family and childhood. Don’t write someone off because he hasn’t spoken to his brother in years and don’t assume someone who’s close with his mom will always be a sweetheart, but do take note of the response to this question.

2. What do you like to do for fun?

Learning about a person’s hobbies and interests is a great indicator how they values their time and what makes them feel passionate. It’s always fun to see when interests overlap – are you both swimmers or did you go to the same concert last year? – but it can be equally fun to find out more about the things you don’t have in common. How did he get into photography? What is it about cooking he loves so much? Finding out how he spends his time can help you picture the way your lives will fit together. Are you cool with him watching a monster truck rally every Tuesday? Are you inspired by the volunteer work he does at the children’s hospital? Are you a little disgusted by the monthly hot dog eating contest he does with his friends? These are good things to know from the get-go. 

3. Given the choice of anyone in the world, whom would you invite to dinner?

It sounds like a trite dinner party game, but here’s another question that can reveal a lot about a person. Whether the answer is Oprah, a professional basketball player, a long lost relative, a former teacher, a long-dead celebrity, or a political figure, the reply can give you a glimpse into what kind of person your date admires or things they value. Ask this question and you may find yourself hearing a very long response – one that tells you a lot about the other person.

4. What three cities would you never, ever move to even for the job offer of your dreams?

This one’s fun because it’s a little bit silly, but the answer will reveal a lot about your date. In fact, whether or not your date takes the question seriously reveals a lot. We all have places we’d rather not go; it’s helpful to know this about each other. If your date would rather die than live somewhere with cold winters, and meanwhile you wanted to go back to the northeastern town where you were raised, you could have a potential problem down the line. If you both passionately agree on not wanting to live in Des Moines or Tallahassee, you have something to bond over.

5. What TV shows do you watch?

You can find out a lot about your potential compatibility with this one. Does your date watch TV? How much? Which shows? Is he into any of the same shows you watch? If you’re a comedy girl and he’s a horror guy, that might be a dilemma. Or if he likes to watch TV at the end of every evening and you’d prefer to watch a few shows a week, this could be a conflict. On the other hand, maybe he’s watching interesting shows you’ve never seen and he wants to introduce them to you. Or maybe he wants to hear more about the shows you watch. There’s only one way to find out if you like similar types of entertainment – ask this question.

6. What do you do for a living?

This may be the first thing you guys talk about. Asking another person about his profession will tell you a lot about not just the line of work itself, but the way he feels about it. Is he passionate about his career? Is he frustrated at work? Does he see his job as a stepping stone for something else or does he feel settled where he is? Does he watch the clock all day long or does he enjoy what he does? Is he where he hoped he would be in his career? You can find out a lot about a person’s ambitions and attitude by learning what he does all day. 

7. What sort of vacations do you like to take?

This question is twofold because first you’ll find out if he has any interesting travel stories. Secondly, you’ll discover if you two share similar vacation goals. That may sound like a silly thing, but if you’re someone who loves to lounge on a warm beach and he’s someone who wouldn’t consider vacationing somewhere where there wasn’t snow and constant activity, imagine a lifetime spent trying to compromise on that. You don’t need to want the exact same things, but it’s helpful to know if he’s going to want to golf on every vacation you take, or if he works so hard he rarely takes vacations, or if he considers a weekend of hardcore mountain climbing and hiking a vacation. 

8. Do you like scary movies?

This is like the TV one. It’s not a huge deal if you don’t agree on the answer, but it’s helpful to know. It’s especially helpful to know if you enjoy going on movie dates or renting films to watch while cuddling on the couch together. Are you going to have to drag him to movies he hates? Do you both agree that horror films are overrated? Does he enjoy foreign films with subtitles and you’re more into goofy comedies? This question isn’t a deal breaker by any means, but it does reveal some important information.

9. What’s the best book you read last year?

Here’s another one that can tell you a lot about whether or not your lifestyles are compatible. If you’re thinking “I don’t even know how to choose one favorite from last year” and he says, “I didn’t read a single book last year,” there’s a marked difference in your responses. It doesn’t mean that a nonreader and avid reader can’t get along (or that someone who only reads stories about sports can’t enjoy spending time with someone who always reads historical romance novels), but it’s again something to note and decide if it’s important to you or not.

10. What do you like to drink?

This one will tell you more about whether or not he drinks, how often he drinks, what kinds of drinks he enjoys, and more. Do you enjoy going to wine tastings and he refuses to drink anything but beer? Does he stick to stiff drinks every night and drink until he’s hammered? Is he sober? Does he have opinions on your drinking habits? Again, these are all helpful things to know.



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