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How to Revamp Your Boring First-Date Questions

Okay, imagine this. You're on a first date. You're jittery, you're palpitating, the works. You've written a bunch of questions on your hand that are now all sweat-smeared and completely illegible. So, ya got nada. Now we've probably all been on dates that end up feeling like a job interview or a high-stakes interrogation. Our date might as well be notating our every UM and LIKE in their ledger of disapproval and judgment. So how can we spice up our conversation so dates feel less like work and more like fun? Here's how to revamp your age-old first-date arsenal to ensure a second one!

What do you do?

Take it from dating sites like EHarmony, that have been dishing out the ingredients to better relationships for years. Their experts advise questions that go deeper and feel natural. The question, "What do you do?" often prompts people to talk about their jobs. A job may be something you do, but how much does it reveal about a potential partner's personality? Instead, try a more pointed question like, "What would you like to do, if given the chance?" This will get your date thinking beyond the neutral territory of the workplace.

What's your family like?

Psychology tells us that a person's family is often a large contributing factor to his or her actions, behaviors, and moral code. A family that shows compassion and gathers often pretty much guarantees a person that will do the same with his or her family. But rather than asking the general, "What's your family like?", invert that question -- "What do you like (and dislike) about your family?" This will get your date to give you some insight on what's important here. When possible, try to keep it positive, but it's also important to note (and watch out for) the negatives!

What is your greatest passion?

Passion is the key to a long, loving relationship, right? And everyone on the planet has a passion, even people that you think are initially, total bores. They key to revamping this question is to point it somewhere specific. Questions starting with "what" will almost always lead to one-word or short answers. Instead, ask, "How did you get interested in X passion?" You want your date to tell you a story, rather than list facts. If you want facts, read an encyclopedia.

What are you looking for in a relationship?

Hold up. Talking about a relationship on your first date is kind of jumping the gun, although it's important to get a sense of what you're getting yourself into. The key here is subtlety. Start with friendship. Ask, "What do your friends like and dislike about you?" This gives them a chance to think about how they're perceived, rather than giving you the elevator pitch about why they'd make the perfect match. You're out to get honest information, not a living, breathing infomercial. Information about friendships will give you a feeling about what he or she might be looking for in a relationship. But hold back the reins on the R word for the time being!

What do you like to do on the weekends?

You'd typically ask this kind of question to gauge whether your date is a museum-going intellectual, craft-beer aficionado, or sports junkie. However, it can often lead to boring answers such as: "Uh, you know. Hang with friends. Watch Netflix. Yeah." You do not want that. One of my favorite questions to ask are hypotheticals. Like, "You have 24 hours in New York City with no wallet. What do you do?" Situations like these can really help spark the conversation and be fun! Give your date a deadline too. I like to say you have 15 seconds. Go! Raise the stakes and make them sweat a little (in a good way!). Hypotheticals work for job interviews too! If ever in the situation, you'd know exactly what to do.

Where do you see yourself in 10 years?

Boooring. The future is something that a lot of people stress over. Will your date be unimpressed if you say that in 10 years you want to live on a farm in North Dakota raising sheep? Instead, attack this with another thought-provoker. Try, "Imagine that you're eighty years old. What advice do you give yourself at your current age?"

What do you think about so-and-so hot bed political issue?

Politics is infamously a huge first date no-no, often bringing down the light mood. Stray away from totally volatile subjects. Instead, try a more general philosophic question. Elite Daily boasts a question such as, "True or false: All is fair in love and war?" This might lead your date to start thinking romantically instead of politically. But try a question such as, "If you could make one change in our country/world/etc., what would it be?" This will get them thinking theoretically. It's fun to engage in intellectual debates as a way to see what issues your date cares about.

Seen any good movies recently?

Psychology Today touts this as a good first date question. It is good in the sense that you'll figure out what kind of taste your date has. But in order to make this more interesting, ask instead, "What was the last movie that made you laugh? Cry? Made you furious?" I like to take inspiration from the New York Times book review profile section. Also, look at other interviews that you find interesting and take note!

What's your favorite food?

Come on, I think we can be a little more creative than that. We all know that food is a super important first date topic, as the way to a man's (or woman's?) heart is, you know. But we can do more with this question. Food, for a lot of people, symbolizes family, emotion, and fond memories. Rather than focusing on food, focus on experience. Ask your date about a really fun and memorable meal they had. This will be a great way to get more stories!

Are you a dog or cat person?

Who doesn't like animals? It's no doubt that humans and animals have an extraordinary connection. But this question is going to spark long, boring stories about someone's pet. While that's all fine and dandy, it would be better to keep the focus on you two. Ask your date about a dream pet, what it's name would be, its personality and lifestyle. This will give you a sense of a person's willingness to get creative. Pet pterodactyl, anyone?

Where'd you go to school?

Trying to parse out whether or not your date is an Ivy-league scholar is not super helpful. Instead, get your date to talk about what he or she studied in school and why the choice was made. If given the chance to change paths, would they? And why? Focus on getting to the meat of what makes your date tick.

Any weird talents?

This can often get awkward and results in boring answers such as, "I can touch my tongue to my nose." Big whoop. Ask instead, "What skill do you have that you wouldn't put on your resume?" Now this opens up the field to much more interesting and creative answers. Don't shy away!

Now that you've dusted off these age-old questions and revamped their style, you'll be well-equipped to handle even the most reticent dates. Remember, there are no wrong answers, only bad questions.

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