Here Are Our Favorite Questions to Ask on a First Date

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I have yet to meet someone who loves going on first dates. And let’s be honest, they’re really tough to navigate! You meet someone online, have a great conversation with them, make a date, and then sit awkwardly in each other’s presence for the next three hours. It’s rough!

But as I have been on my fair share of first dates, I’ve also learned the best way to navigate that awkward first encounter and make your dinner date into one of the most memorable (for good reasons) first dates you’ll have ever gone on.

In truth,  there isn’t a right or wrong way to approach dating. And while the lack of a rule book usually works in our favor, it also leaves us a little (or a lot) confused when we get to events like the first date, where everything is topsy-turvy, and there are no ground rules. Suddenly, everything feels very off and unstable, leading many people to feel uncomfortable and insecure. 

But we don’t want you to feel any of those negative emotions when you’re approaching your first date, so we’re sharing our favorite tips and tricks to make you have the best first date ever. From conversation starters to general information for your first date, we’ve got you covered, and we’ll help you have the best first dates from now on. 

If you’re wondering how to not only conquer but slay your first date with anyone, here are our suggestions for going on the best date ever.

Why Are First Dates So Awkward?

Let’s face it — first dates can be really awkward and uncomfortable. There’s a huge sense of unfamiliarity looming in the air, and it’s hard to feel comfortable when there are so many unknown factors, people, and moving parts. Unless you’re going on the most casual first date in the world, you’re probably dressed up and wearing a different look than you would be in your everyday life. 

Not to mention, if you are going out with someone you met online, this is your first time actually seeing them in person, and it can be a bit jarring. While we love online dating and all of the connections it allows people to have with people from all over their areas, we can all agree that the first time meeting someone from the online world in real life has a ton of expectations, hopes, and pressure riding on the one interaction. 

So, in a way, first dates are like interviews. I know, doesn’t that sound romantic? But they are a kind of vetting process that many people use to see if the person they’ve been talking to online for such a long time is really as good as they seemed at a distance. 

A tip I always give people when they’re stressed out about their first date is to think of some general topics and things they want to say beforehand.

We’re not saying you should write an entire movie-level script for your first date because your date won’t know their lines. It will get messy, but we have a general idea of things to say if the conversation lulls or there are some awkward silences. 

One of the best ways to steer the conversation and get it going is to ask questions. Remember, it’s a first date, so you and your date probably don’t know that much about each other; that’s what the date is for! So by asking questions, you’ll not only learn more about each other, but you’ll also be able to keep the conversation going and enjoy your time out together. 

Also, don’t worry. The questions you ask your date don’t all have to be super deep or all geared toward assessing if the person you’re going out to dinner with is your future spouse. Sometimes, it’s best to ask a dumb or low-stakes question to ease any tension that might sprout up and get the conversation rolling. 

Here are some of the best questions you should ask your partner on a first date. 

  • What is one thing that never ceases to make you smile?
  • If you had to choose one TV show to watch for the rest of your life, what would it be?
  • What is one book universe that you wish was real, and why?
  • What is one thing you wish you could learn if money and time were not an issue?
  • What is your biggest pet peeve?
  • Are you currently working on any passion projects?
  • Do you like what you do for work? Would you still do your job if they didn’t pay you or didn’t pay you as much as they do?
  • What is one thing you love to do when you need to kill a few hours?
  • What is the best present you have ever given someone and why?
  • What is the best present someone has ever given to you and why?
  • What hobbies do you have?
  • What is your Hogwarts house?
  • If you had to teach a class on one subject right now, what would it be and why?
  • If you had to give a TED talk on one topic right now, what would it be and why?
  • What does a typical day look like for you?
  • How do you like to spend your weekend?
  • Are you a morning bird or a night owl?
  • What is one morning ritual or routine that you have to start your day with?
  • Do you like to travel, or would you prefer to stay home?
  • What kind of vacations do you like to take?
  • What are the biggest red flags that you tend to avoid?
  • What would your friends say are the biggest red flags that you have?
  • What is the best advice someone has ever given to you and why?
  • What is the best advice you’ve ever given to someone else?
  • Do you have any pets, or are you open to having pets?
  • Describe your closest friends in a few words; why do you like being around them?
  • What is one road trip snack you have to have every trip?
  • What were you like as a kid?
  • Do you play any sports right now? Did you play any sports growing up?
  • What do you do to get active? Do you go to the gym? Do you go on walks?
  • What is your favorite food?
  • What is your favorite restaurant to go to in this area?
  • What is the wildest thing you have ever done?
  • What is the most out-of-character thing you have ever done?
  • What is one odd talent that you have?
  • What, if any, causes or charities are you the most passionate about right now?
  • What is the last thing you read?
  • What do you listen to when you’re in the car?
  • What style of music do you most resonate with?
  • What are you looking for in a relationship right now?
  • What is the best movie you’ve seen recently, and why was it so good?
  • Do you like video games or board games more?
  • What is the nerdiest thing about you?
  • If you could make everyone in the world read one book, which one would it be and why?
  • What does your perfect Sunday morning look like?
  • Do you have any comfort shows that you’ve rewatched an embarrassing amount of times?
  • If you could move anywhere in the world, where would it be and why?
  • What is one thing you’ve been really excited about recently? (Bonus points if they say this date!)
  • What is your favorite way to unwind after work?
  • Are you working toward any particular goals right now? Are you conquering a huge project at work?
  • Would you rather listen to a podcast or a song? What is your favorite podcast or song?
  • Would you describe yourself as organized?
  • Describe yourself in four words.
  • Are you more of an indoors or outdoors kind of person?
  • Who is the most fascinating person you’ve met, and why were they so fascinating?
  • What is one subject or topic you know far too much about? Why do you know so much about it?
  • How many siblings do you have?
  • What was your dream job as a child, and what is your dream job now?
  • What would your friends say you were best known for?
  • What is something that you’ve accomplished that you’re really proud of?
  • What is something everyone should try at least once?
  • What is the best thing that has happened to you this month?
  • What were your New Year’s resolutions?
  • What is your favorite app on your phone?
  • What is the silliest or most irrational fear you have?
  • What is one thing you want to come out of this date?
  • What are some assumptions you have about me?
  • Why did you agree/ask me on this date?
  • What about me stood out to you?
  • What do you want in your ideal person?

Tips to Ease First Date Fears

If you’re like me and can honestly think of nothing worse than going on a first date (no, seriously, I hate them), then you might not just want some easy-to-use dialogue. You’ll also want some tips and pointers to have the best date ever. 

Keep a Healthy Mindset

The first thing you’ll want to remember when you’re approaching dating and first dates, in general, is that they’re all about your mindset. I know it’s easier said than done to have a positive attitude about something that might make you feel all kinds of nervous, but just establish a healthy point of view for what the date is – just a date.

It’s not the end of the world if your date doesn’t work out or go the way you wanted it to.

That just means it might be time to hop back on Bumble and start swiping again! Yes, we understand that that’s not typically the end goal for most dates. Still, it does provide some comfort to remember to have a healthy mindset and outlook when you’re approaching your date. 

Don’t Put too Much Pressure on Your Date

I get it; no one wants to be stuck in the dating phase of life for too long, especially if you’re on the hunt for something long-term or even permanent. That being said, if you expect every first date you go on to be magical, fireworks, and Bachelor-level amazing, you will be disappointed. I know this isn’t the news you wanted to hear, but it does help you put the first-date pressures into reality.

My first date with my now fiancé was at Target. We had no goal for it, we planned it four hours before it happened, and it was the best date I’ve ever been on. The minute that you stop putting so much pressure on what you think the date should be like and should feel like is when you allow the date to succeed. 

Sit in the Awkwardness

Ah, the inevitable awkward silence that comes on first dates. While it’s good to take some of the above suggestions and start a conversation during some of these awkward silences, it also might be good to sit in the awkwardness for a bit.

Now, if it’s been five minutes and no one has said anything, this might be a red flag. But awkward silences are a natural part of being in a relationship with another human being. It might be good to gauge your comfort level when you’re around someone, and there’s nothing to say. 

I’ve been in a relationship for over three years, and I still have some awkward silences whenever we go out on a fancy date. It’s a little unnerving to go to a new setting and sit opposite someone for dinner.

You’ll have awkward silences come up a lot more than you might think. Instead of rushing to cover the silence with one of our amazing questions, sit in the quiet and see how you feel about it. 

Another thing to note when you’re sitting in the silence is whether or not your date is trying to keep up the conversation as well or if they’re letting you do all the work. Granted, they might feel awkward or shy as well, but if you encounter a few too many awkward minutes of silence and you start to notice that your date isn’t doing anything to keep the conversation going, you might want to raise a little beige (not red) flag and keep going. 

Be Yourself

Yes, the cliche is a cliche for a reason. I know that everyone tells you to be yourself online and in your profile, but it is still so important to be yourself on the first date. Yes, you want to put your best foot forward and look great and be impressive. Still, you also want to take the time during your first date to establish yourself and unapologetically be that person.

Trust us when we say that it will end up being a waste of your time if you try to be or present yourself as someone you aren’t when you’re on your first date. On the one hand, if the person you’re dating is attracted to that skewed version of you, they’re not only attracted to someone who doesn’t exist, but you also will feel less confident because they’re not attracted to the real version of you. After all, you didn’t give them a chance to know that person. 

We know that first dates can be incredibly difficult to navigate and feel confident on, but we want to give you these tips, tricks, and conversation starters for you to feel your most confident and have the best first date ever. 

confused woman looking at phone with question mark background and a heart-shaped speech bubble with a surprised face emoji inside of it

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