It's really in your best interest to ask your date a lot of questions. (Illustration by Hannah Delmore, Kent State University)
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It's really in your best interest to ask your date a lot of questions. (Illustration by Hannah Delmore, Kent State University)

Leave ‘So tell me about yourself’ to the job interviews.

First dates are some of the most emotionally unfamiliar, topsy-turvy times that people willingly set themselves up for. Besides the location and your looks, conversation is really at the heart of every first date’s destiny.

In order to have a sure-fire fun time, the right questions have to be foolproof and planned out accordingly, in case uncomfortable silence strikes. Here are five first-date questions that will help you find out exactly who the person sitting across the table from you is.

1. What’s your signature/go-to drink?

While this question might not jumpstart an in-depth, life-changing conversation between you and your date, it is still a fun way to kick things off. Experts suggest that starting with this question “helps you understand their personality.”

A lot can be said about a person based on their food or drink preference. You can figure out if they are indecisive, confident or addicted to one specific brand of fair-trade coffee from a simple stroke of curiosity. As a bonus, asking about their favorite/least favorite alcoholic beverage can bring up funny or even horrific stories from college that can break the ice, get you both to laugh, loosen up the nerves and even help you discover your newest alcoholic treat.

2. Tell me about your closest friends

Obviously, this is a great tell-all about the person squatted up across the candlelight. In an interview with Bustle, relationship expert Dr. Karin Anderson Abrell said, “Asking them what their friends say about them provides them the safety of describing themselves from another person’s point of view.” First dates shouldn’t resemble harsh, pressing job interviews, so keep it fun and flirty while still probing at the internal hardwiring of your date.

Timing is imperative, so bring this question up after an unfamiliar name pops up or a relatable topic of friendships funnels in. Keep in mind, people love talking about their friends and themselves, and you might have to set a timer for when it’s your turn to speak, so they aren’t dragging on about how wild their homies were on spring break in 2015.

3. Are you working on any passion projects right now?

It’s one thing to ask what you like to do in your free time or about career, but those questions are very … blah. Spin the mundane questions on its head and ask about passion projects or ambitions, because you never know what quirky interests someone could be devoting their time to.

This inquiry spills out naturally once your date mentions how “oh so busy” they have been as of late. Even if they don’t mention any sort of project they are working on now, keep the conversation flowing by shifting into their dream passion project or if they are interested in starting one soon.

And, if all goes according to plan, sparks might flicker off the plug you just inserted about hobbies, free time and devote interests. You never know if compiling 19th-century postcards from around the world floats their boat just the same.

4. Are you more of a pick-up-and-go person or a detailed planner?

If you are looking for a tell-all question that can unlock the gold mine of compatibility of you and your partner — this is it. You can use this question at any part during the date, gearing it toward vacationing habits or just everyday life.

Even if you don’t see eye to eye on lifestyle preferences, it’s not the end of the world, but it might cause friction down the line if the first date turns into a full-blown relationship. While it’s not impossible for the “planner” and the “winger” to live happily ever after, tensions can arise when you both want to take an intercontinental trip or just a weekend away. Speaking for myself, I am a pick-up-and-go type person, and having someone plan every minute of the day would not be welcomed with open arms.

This question exposes a person’s mentality of how life should operate, and either it turns you off or it gets you riled up, depending on your stance and how you handle others.

5. Are you seeing anyone right now?

Asking your date if they are already involved with someone is the most basic yet telling question. Be upfront about this and don’t be afraid of the response. Depending on what you hope to get out of the date, this could either be a godsend or dreadful — furthering your involvement in this person or slashing all hopes.

You should keep your intentions clear for the entirety of the date and reflect on them periodically throughout, as to not get confused about what it is you are doing there. No one wants to have the most life-changing first date, only to stalk their social medias and find out they are seeing someone. Save yourself the potential for unfortunate nature of situationships and soul-crushing heartbreak!

Overall, first dates can be super enjoyable if you let yourself be vulnerable and open to personal, funny or deep questions. In order to gauge someone’s personality asking one or two of these questions can go a very looooong way than just your stereotypical “So, tell me about yourself.”


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