September may have just started, but I have something to put you in the perfect mood for the Halloween spooks: the first date (boo). What bigger “yikes” stories than those of the dating world? Your date shows up wearing a fedora, they say their ex was “crazy” or, and the biggest yikes of all, they waste your damn time. You might want a long-term relationship or to just avoid a lull in conversation.
Either way, read on for these 21 questions to keep all the first-date cringe at bay.
1. Super Power
It’s a bird, it’s a plane, it’s possibly your next compatibility test. “What super power would you have? It shows someone’s creative side and it’s not too serious. It’s kind of unexpected. There’s so many options, too — it can lead into a lot of other conversation,” said University of Iowa senior Amy Jones. This kind of question can stem in all kinds of insights on your date, as well. Do you want to fly because you want to travel? Do you want to have immeasurable strength so you can help other people? And of course, the less conventional ones give way to a lot of intrigue, too. For example: never having to go to sleep so you can get all your work done. Wild.
2. Career Ambitions
A good way to determine compatibility? Ambitions, especially regarding their future. “I feel like asking someone what their ambitions are, career-wise,” said University of Iowa sophomore Lauren Whitney. Have at it. Just try not to make it seem like a career counselor asking a student about their four-year plan. See what they’re excited about with their potential careers, what they want to succeed in and how they want to do it.
3. Horoscope
Yes, I will include this question, you knew it was coming. Horoscopes, whether you like them or not, made their way into common culture via social media, and you best believe they’re here to stay. Even if you don’t like them (and I get it, to all the bullied Geminis), this means you get to find out whether or not your date obsesses over them to a degree you don’t vibe with. Or you discover that their rising Capricorn corresponds perfectly with your rising Taurus, and boom— match made from the stars.
4. Music Taste
Depending on your personal preference, this often has a make-or-break factor to a first date. “You have to know what their music taste is. You can tell a lot about a person from their music taste,” said University of Iowa junior Jessica Peña. Seriously, what if your primary music interest horrifically clashes with theirs and you can’t jam out with them on car trips? I’m not naming names, but show tunes don’t mesh well with heavy metal. Better to find it out now than later.
5. Childhood Passions
What did you want to do when you were little? You know for a fact that every kindergarten classroom had some variation of that question, usually in obnoxious primary colors. Even if it’s something as stereotypical as a princess or an astronaut, it calls to mind some particularly cute or ridiculous kind of childhood stories. Nothing’s more relatable than eating sand or trying to cut your own hair as a child. Whether or not I’ve had personal experience with these stories is up to you to decide.
6. Movie Taste (aka Disney Taste)
Thank the heavens above we live in a culture where it’s still acceptable to binge-watch Disney movies. “What their favorite movie is, and more importantly, what their favorite Disney movie is. If they don’t like my favorite Disney movies, I can’t date them,” said University of Iowa junior Kim Fernandez. I personally find this trait more telling than most traits, so I live to know the answer to this. Note: saying “all of them” does not equate an acceptable response. Fox and the Hound or The Aristocats, Snow White or Aladdin, dang it.
7. Reasons for Your Major
While I’m hyper-aware of the “awkward freshmen conversation” connotation behind this question, I have solid reasons for this one. You know for a fact that choosing a major can either feel as easy as picking a favorite Friends character (Chandler, obviously) or as difficult as picking a favorite Parks and Recreation character (a ride-or-die Ben Wyatt stan, personally). From that, ask the genuine questions: did you always know you wanted to pursue this major? Was it easy or hard to choose and why? It unveils a lot of someone’s personality by the way they answer. Plus, you’ll have time to get into it when you aren’t asking at a crowded lecture hall/frat party.
8. Passions
This question can give way to all kinds of conversation, more or less dependent on you and your date. “What are you passionate about? That’s a good one to get someone’s personality from,” said University of Iowa sophomore Holly Dannen. The answer and ensuing conversation can go from light small talk to deep medium talk. Do you want to talk about your casual collection of stress balls, or do you want to talk about your favorite distant relative? The choice is yours, and can likely result in either a second date or a good story, at the very least.
9. Favorite Teacher
Teachers inspire us, transform us and often pave the way for how we think. So, hell yes, I want to hear about the person who led you to become who you are today. And they could have found a place in your heart for several reasons. Maybe they gave you the idea to pursue a particular career. Maybe they were even just a cool person to learn from or hear stories from. Regardless, it makes way for some wholesome conversation.
10. Education
If you met your date in a classroom, it’s likely that they currently attend a university; however, it usually goes deeper than that. “’Are you a student, and why or why not?’ I always want to ask that, because there’s usually a good reason behind their answer,” said University of Iowa senior Ben Brewer. If they go to university, do they know why? Was it what they were always told to do, or did they go with a specific goal other than obtaining a degree? People don’t always go to college, either; several careers and vocations don’t require a college degree, and they usually have a fairly good reason for not attending. From here, a lot of medium talk can ensue.
11. Guilty Pleasure
This phrase could mean anything, from asking their favorite “gross” snack to their favorite cheesy film or book to pore over after-hours. Nothing tells a personality quite like their desperate explanation defending deep fried butter or the latest Nora Roberts book. Establish a judgment-free zone with your date and let the resulting laughter tide you both over to that second date.
12. Family
Considering that they’ve likely lived with their family their entire life, this gives you a solid idea of what your date is like. “What they love about their family. Definitely the way they talk about them can show a person,” said University of Iowa junior Calvin Collins. This has the potential for so many lovely stories, too: maybe they have an uncle that dresses up as Santa every Christmas for the kids, or their cousin just gave birth to a second baby. It’s likely they’ll show the baby photos, too, if you’re a fan of cute babies and whatnot.
13. Traveling
As someone who personally gets starry-eyed from the thought of traveling, I find this a good way to gauge a person’s interests as well as personality. If they want to travel, where and why? What sights do they want to see? Your date could want to travel all over Europe and see the art history sights of the Louvre and Pantheon. Perhaps they want to go on a big hiking trip through rainforests and camp out in hostels or the foliage. They could not want to travel at all due to other interests or goals currently in the works. Whether or not the two of you agree, it makes for really interesting insight into your date.
14. School or Work Stories
As certain as the day is long, the life of the student and/or worker will be full of hilarious grievances. “What’s the tea? I want to know the work or school drama,” said Brewer. There’s no real bonding technique like mutual hatred of people, after all. Try not to delve too deep into the drama when recounting your own horror stories, however. Talk about your annoying professor or a customer who didn’t even tip on a big order (because I assume your date will be cool enough to tip their servers, too).
15. Most Irrational Fear
With irrational fears stemming everywhere from fear of holes to the fear of peanut butter sticking to the roof of your mouth, your date will inevitably hold a fear of something pretty wacky. Ask away and see what kind of kooks they enforce to avoid cracks on the sidewalk, or what kind of tactics they employ to avoid any and all advertisements of Shark Week. As I have mentioned before, ensure that you have a mutual judgment-free zone for all your irrational fear needs.
16. Friends
Assuming that your date spends the most time with their friends, asking about them entails you discovering a lot of what they’re like, too. “I like to ask questions about friends that they have, because usually based on stories they tell you about what they do with their friends, you can kind of feel them out,” said University of Iowa senior Delany Breitbach. It helps to ask about any funny stories they share with their friends, or even how they became friends with their best friend. Possible results can include smiling, laughing and perhaps even a genuine connection.
17. Favorite Fictional Character
Another one that can give away so many traits about a person: their favorite show or movie, who they want to emulate in life and, of course, who to stay the hell away from. “Who is your favorite fictional character? Because you can tell how pretentious they’ll be or if your senses of humor will match up,” said University of Iowa senior Natalie Betz. For example, if their favorite character happens to align with certain toxic masculinities (cough Fight Club), then you know exactly who you’re dealing with. On the other hand, if their favorite character lies in your favorite independent film, or makes your entire body ache with laughter, then you may have yourself a keeper.
18. Favorite Things to Do
Because a first date likely involves a pretty surface-level location and itinerary, it’s important to know the places and activities they actually frequent. “Get to know their favorite things to do, because you definitely want to match up on that,” said University of Iowa junior Lily Colvig. If you both enjoy hiking, set up a future nature trail kind of date, or schedule the next independent film if you both love a certain director. Even in the chance that your interests don’t quite correspond, it’s always interesting to have a conversation on differing hobbies.
19. Funniest Drinking Game
This might not apply to people who don’t drink or all of you suckers below 21 (without fakes), but even so, it’s entertaining to discuss the ridiculous kinds of drinking games that often ensue from films or regular games. This point of conversation gets even better if you or your date have horror stories from a drinking game. Did you have to drink every time someone sang in Mamma Mia? Did you play the True American Drinking Game from New Girl? Effectively, this brings out the rowdier, and often more candid, side of your date.
20. Future Plans
This idea often goes hand in hand with their career, and often shows what they want out of a career. “I think asking about future plans is good because you can tell if they’re just focused on money or actually doing what they like,” said Breitbach. Even if making money does hold high priority on their list, you can decide whether this matches up with your own life goals.
21. Bucket List
Asking about a person’s bucket list might seem a little morbid at first, but I can guarantee you’ll get some really cool answers if you ask. Even if you don’t think you have a bucket list, you certainly have some out of the ordinary tasks or achievements you want to accomplish before you kick that ever-inevitable bucket. Do you want to sit in the Iron Throne, located in Dubrovnik, Croatia? Do you want to gain the ability to knit the perfect sweater or bake the perfect cake? Maybe you even want to sail across the Atlantic Ocean, or see every major mountain range in the world. No matter how ambitious or realistic you find the list, it leads to fun conversation as well as finding out your date’s hidden passions in life.
