9 Out-Of-The-Box Questions To Ask On A First Date

by Laken Howard

If there's one thing I've learned from years of online dating, it's that first date conversations don't always come naturally. When two people meet for the first time, it's normal for nerves to impede what might otherwise be a fun night of flirting and bantering. There's nothing worse than being on a date with someone you're actually really interested in, only to let anxiety get the better of you and keep you from putting your best foot forward.

"For the most part, first dates are incredibly pressured, self-conscious experiences where you are often preoccupied through the whole experience about how you are coming across to the other person," Rhonda Milrad, founder and Chief Relationship Advisor of Relationup, tells Bustle. "It is actually hard to focus on getting to know your date because you are so focused on your date’s reaction to you."

The one silver lining? For the most part, people are a bit more forgiving on a first date, because everyone knows first impressions (while important) aren't always totally accurate. While you definitely aren't obligated to go on a second date with everyone you meet, it's worth remembering that people aren't always themselves on a first date. "I don’t think first dates are a good indicator of whether you and your date are well suited for a romantic, long-term relationship," Milrad says. "[However], they are great indicators of whether you and your date are sexually attracted to one another and there can be a lot of chemistry and energy based on this."

On a 'good' date, you shouldn't need to have note cards with questions on them to help conversation flow. However, when nerves are running rampant, it's still a fun idea to have a couple atypical questions in mind that will break the mold and tell you a little something about your date. Here are fun questions to ask on a first date that can help you assess your connection.

1. What's The Last Show You Watched?

Netflix-ing is one of the great Millennial pastimes. Although conflicting TV tastes is (hopefully) not a deal-breaker, it's worth asking about your date's tastes so you can get a glimpse of what a rainy Sunday on the couch might look like with that person.

2. What's Your Job Like?

Talking about work on a first date may not sound like fun (can't you ever get a break from the office?), but it's a worthwhile question for a lot of reasons. "Get your date talking about his or her job and career and you’ll get a tremendous amount of insight into their ambition, education, career plan and lifestyle interest," April Masini, relationship expert and owner of AskApril, tells Bustle. "This is a huge glimpse into whether or not someone is compatible. If they’re chronically unemployed or just happy being a temp, you’ll get insight into that aspect of their life, as well."

3. Are You From The Area?

"We live in a world where lots of people are from places other than where you’ve met them," Masini says. "When you ask about how they got to the place you both met, you can learn a lot about their story, their family, their motivation for moving, and how or whether they keep in touch with family and old friends." This is especially true of people in huge metro areas like NYC, Chicago, LA, or DC — it's super likely that anyone you meet is from somewhere totally unexpected.

4. What Superpower Would You Most Like To Have?

Personally, I'm not a huge fan of this question — I find it a little cheesy and hard to work into conversation naturally. However, it's definitely one that gives some insight into your date's character if you can work it in well. "You can tell so much from the answer, or lack thereof," Crystal Rice, licensed therapist at Insieme Consulting, tells Bustle. "Do they really give the question the time of day and think through an answer? Is their answer focused on helping others? Is their power selfish in nature? Are they creative with their response, or do they go for the 'normal' stuff and then move on?"

5. What's Your Favorite Holiday Tradition?

This question is a goldmine for connection-building, especially now that the holidays are swiftly approaching. Maybe your date and their family goes caroling every year, just like yours — you won't know unless you ask. This question presents your date with the opportunity to talk about a myriad of things: family, friends, childhood memories, and more. Before you know it, the two of you could be planning a trip to the ice-skating rink as a #TBT to your younger days.

6. What's Something You Consider A Guilty Pleasure?

Although I have a bit of beef with the concept of 'guilty pleasures' (why should we ever be ashamed of what we like?), this is a fun question to ask a date nonetheless. It gives you an idea of what your date is passionate about, and helps you both open up about something that might be seen as 'embarrassing' by someone more judgmental. Who cares if you (read: me) reread Harry Potter several times a year? Open up to your date about what you love, and a connection is sure to follow.

7. What's The Most Memorable Vacation You've Taken?

Although not everyone has the means to travel all over the globe, it's likely that everyone has at least one awesome vacation memory that they reminisce about still. This question tells you something about your date's past, while inviting them to talk about places they'd like to go in future. If you both want to experience Bangkok, it's something you can bond over (even if it's only a pipe dream).

8. If You Could Pick Up Any Skill Instantly, What Would It Be?

In a perfect world, we'd all have unlimited leisure time to do fun things like learn to make macarons or play the piano. In reality, we have to choose how we spend our free time wisely, and there isn't always time to devote to new hobbies or to learning new skills. This question gives you a different kind of insight into your date's personality than simply asking what their current hobbies are, because it shows you what kind of activities fascinate them — even if that thing is a tad difficult to get into. Who knows? You might both take a sushi-making class together as a result of this convo.

9. Who Was Your First Kiss?

Though it's probably not a good idea to bring up your exes on a first date, this question is an innocent glimpse into your date's romantic past. It gives them the opportunity to talk about the funny, awkward parts of their childhood, and gives you a look into who they crushed on as an adolescent. And let's be honest: there's a good chance you both had your first kiss at summer camp, which is always something two people can bond over.

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