25 First Date Questions

people clinking glassesIs there a higher pressure situation than a first date? Here you have from 30 minutes to maybe two hours to impress your date and prove that you’re not a psychopath, while attempting to find out how impressive your date is and whether or not they’re a psychopath. In essence, what you’re doing is a job interview for the position of soul mate, friend, friend with benefits, one-night hookup, or whatever sort of relationship you’re looking for.

A job interview requires questions and the interview for your romantic partner is no exception. While the temptation is there to turn on the hot light and perform an interrogation that would make a North Korean prison guard proud, in order to avoid looking like a psycho yourself you’re going to want to sprinkle a few questions into normal conversation and not employ any torture devices—you can save that for the third date, if you’re both into it. But what questions should you be asking on a first date? Here are a few suggestions:

1. Are you married?
It’s a shame that you have to ask this, but the fact is that people come up with all sorts of ways to avoid giving this little piece of information to a potential date. Sometimes a direct question is the only way to get a direct answer.

2. Do you have any kids?
This is another one of those things that it’s best to find out early on in the dating process. If kids send you into fits of uncontrollable rage, it’s best to find out that your date has octuplets before you go for dinner at her house. It’s also a great conversation starter if you like kids, because every parent loves to talk about their kids.

3. Do you have any siblings?
Psychologists have written volumes about the difference between an only child and a child from a large family, so odds are that the number of siblings one has will affect how they behave in relationships, too. This question will also often give you some insight into your date’s ideas about family.

4. What’s on your bucket list?
In some ways, people are really the sum of their dreams and aspirations. If the man of your dreams has banging his top five favorite porn stars on his bucket list, you might not be looking at a future PTA dad. If, however, you both want to visit Barbados before you kick the bucket, you may have found a future vacation plan. Or a honeymoon.

5. Has your heart ever been broken?
It may seem dangerous to bring up heartbreak on a first date, but sometimes it works. Someone has to have a heart to get it broken, so a positive answer to this question is good news, unless they have taken a vow of bloody, violent revenge.

6. What’s the longest you’ve been in a relationship?
Past performance can sometimes predict future performance. If their average relationship is 14 years, they may not be the quick hook-up you’re looking for.

7. When did your last relationship end?
You don’t want rebound, so if the answer is “Yesterday,” you might want to let your date cool off a bit before you start dating them seriously. Similarly, if their last date was 1979, there are probably going to be some issues to deal with.

8. How did your last relationship end?
Again, the blood oath of violent retribution against a former lover is usually a bad sign. Another bad sign is if their former boyfriend or girlfriend is living with them in a “friends with benefits” situation.

9. Where do you want to be five years from now?
True, you may not be looking for someone you expect to even be speaking to in five years, but knowing that they have a plan will at least show that they are capable of cognitive thought.

10. Which city would you rather visit, Paris or Vegas?
You can’t assume that every person who wants to visit Vegas is a drunken, horny gambling addict any more than you can assume that anyone who wants to visit Paris is a pretentious, anti-American hipster, but you might get a little more insight into someone’s personality based on how they answer this question.

11. Are you a morning person?
Our body clocks are very important to our overall compatibility. If you like to get up at the crack of noon and your date is up before the sun every day, good luck finding common times to go on dates.

12. If you could only rescue one possession from your burning house, what would you choose?
The safe answer is always family photos, but if she says she’d save her favorite vibrator, you could be in for a wild night, or several.

13. Which high school subject was your favorite?
This question could be a struggle for two fifty-year-olds on a first date, but it does tell a lot about where your interests lie. It’s nice to get back into the high school frame of mind, too, because you just might both get nostalgic about making out behind the bleachers at Homecoming.

14. What’s the most embarrassing thing you ever did?
It might be hard to get someone to open up enough to reveal this on a first date, but it could lead to a really funny story, and laughter is a great aphrodisiac. Of course, the downside is that you’ll be expected to share your most embarrassing story, too.

15. What animal is your favorite and why?
This is another one of those great conversation starters. Even if their favorite animal is a centipede, there will be some follow-up questions and a chance to share your own views on the animal kingdom.

16. How often do you speak to your parents?
How a man treats his mother is how he will treat his girlfriend, as scary as that may seem. Beyond that, your relationship with your parents says a lot about your upbringing and your values—all things that come into play in a dating relationship.

17. When you were a kid, which book or story was your favorite?
So much of our childhood helps to make us who we are as adults. If a girl’s favorite story was “The Princess and the Pea,” you may not be able to afford her. If a guy’s favorite story was “Green Eggs and Ham” he’s probably not a great cook.

18. What do you normally order when you go to a coffee shop?
Everybody has their coffee quirks. If you’re a straight Folgers drinker and your date orders a soy, half-caf, caramel macchiato with a light dusting of chocolate shavings, you may not be the two most compatible people in the world. If your date doesn’t drink coffee at all, they’re definitely not to be trusted.

19. Do you have a pet?
People love to talk about their pets, sometimes too much, so this could get the conversation going and it could make you wish you hadn’t. Still, the ability to care for a pet does show the capacity to love.

20. What year was your favorite and why?
Everybody has a favorite year—for some people it might be as simple as the year they graduated high school and for others it could be the year they dated a supermodel, won the Nobel Peace Prize, and figured out how to set up the DVD player and the Wii system on the same television. In any case, it gives you more information about what makes them tick.

21. If you learn to speak one more language what would it be?
This question could be a dead end or it could lead to an interesting story about your date’s heritage and travel dreams.

22. What is the longest current friendship you have?
If you want to know about the loyalty of the person you’re dating and how easy they are to get along with, you need look no further than their friendships. If they have a close-knit group of friends who have been with them for decades, it’s a good sign. If their dearest friend has been in their life for three weeks, maybe they tend to drive people away.

23. Where was your last vacation?
People are usually proud of their vacations and they like to talk about them because they are often happy times in their life. Of course, if their memories include wistful descriptions of making passionate love with their ex on the beach, you might want to change the subject.

24. What was your favorite TV show when you were a little kid?
Again, who we were as children influences who we are now. We all remember our favorite TV shows from our childhood and talking about them will renew that childish sense of adventure in us. Besides, maybe you’ll find that you were both huge fans of some obscure cartoon that will bond you for life.

25. If you could live any place in the world, where would you choose and why?
Who knows, maybe after they answer this question you’ll both run off to Alaska together to mine for gold and fish for salmon. Or maybe you’ll discover that they want to live in a desert and you want to live on the beach and this relationship will never be more than a quick fling.