(That Aren’t Boring)
So, you’ve got a first date coming up—super exciting! Maybe you’re dipping your toes back into the dating pool, meeting someone from an app, or saying yes to that friend-of-a-friend setup. First dates can be a whole mix of emotions. Nerves, excitement, curiosity, and maybe even a little panic over what to wear or what to say. We’ve all been there.
One of the biggest worries people have about first dates? Awkward silences. You know, those moments when your brain blanks and you start overanalyzing your water glass. That’s where having a few thoughtful, fun, and flirty questions up your sleeve can make all the difference.
Advice. Read this and prepare for counter questions.
The goal isn’t to turn the date into an interview (because yikes), but to create a natural flow of conversation that helps you get to know each other in a real and relaxed way. The right questions can spark laughs, deepen the connection, and help you figure out if this person might be someone worth seeing again.
No matter how nervous you get, remember to actually listen to this person. Actually listening and showing interest in what a person says is huge. Nobody wants to feel unheard.
Pick and choose some questions you want to ask. Some of these are pretty straightforward. I am a pretty straightforward person so they fit my personality pretty well. If you wouldn’t feel comfortable asking a question or getting an answer to one of these, leave it out. Always be yourself.
Below, I have compiled a list of my favorite questions to get to know the person you’ve agreed to go on a date with. Keep in mind, this is a date and not an interview. Like I said, maybe find a couple questions that you can ask if there is a bit of awkward silence and find ways to keep the conversation flowing. Remember, you both like something about each other or you wouldn’t be here in the first place. Always be yourself, but have some fun. Laugh and don’t think too hard.
Whether you’re looking for something lighthearted, meaningful, or just a good conversation starter, this list has you covered. These questions are designed to keep things easygoing and enjoyable—no pressure, no scripts, just good vibes.
So, take a deep breath, smile, and let’s dive into 40 of the best first date questions that will keep the convo flowing and help you make a memorable impression.
- What is something you’ve always wanted to try but never had an opportunity?
- If you could pick a superpower, what would it be and how would you use it?
- If you could go see a concert today, who would you see?
- What is your soul music? Go to music genre?
- If you won the lottery tomorrow, what would be the first thing you’d buy?
- Do you have a bucket list? How many things have you actually done from that list?
- Mountains or ocean?
- What is your happy place?
- Do you believe in ghosts or aliens?
- Would you ever stay the night in a haunted house/hotel?
- How many tattoos do you have?
- Who is your celebrity crush?
- What was your first job?
- What is your ideal date?
- How do you deal with stress/anger?
- Have you ever been arrested?
- What is your favorite drink?
- Are you a conspiracy theorist?
- What type of movie/show are you into?
- How jealous are you on a scale from 0-psycho?
- Do you let your past relationships affect new ones?
- What is your biggest pet peeve?
- Do you like to cook?
- What is your type?
- Do you believe in soul mates or love at first sight?
- What red flags do you look for in dating?
- Are you an introvert or extrovert?
- What 3 words would you use to best describe yourself?
- What about your favorite holiday makes it your favorite holiday?
- If you could choose a time frame to live in, when would it be and why?
- What’s the scariest thing you’ve ever done?
- Are you or have you ever been addicted to anything?
- What is the best piece of advice you’ve ever received?
- Cats or dogs?
- If you were forced to enter a talent show, what would your talent be?
- What are your thoughts on Zodiac?
- Do you snore?
- What’s your worst habit?
- What do you like to do on your days off?
- Are you a planner or more spontaneous?
Final Thoughts: Let the Conversation Flow
At the end of the day, a first date is really about connection. It’s less about saying the “perfect” thing and more about showing up as your real, authentic self. These first date questions aren’t a checklist or a script—they’re simply conversation starters to help you skip past the surface-level small talk and get to the good stuff.
Whether you’re swapping favorite travel stories, laughing over guilty-pleasure TV shows, or discovering a shared love of sushi, asking the right questions can turn a so-so date into something truly memorable. And even if the spark isn’t there, you’ll still walk away with a fun conversation and maybe even a great story to tell.
Just remember: dating should feel exciting—not stressful. If the conversation flows easily and you find yourselves smiling more than checking your phones, that’s always a good sign. Keep things light, stay curious, and don’t be afraid to let your personality shine.
And hey—don’t forget to listen. Asking great questions is just one part of the puzzle. Being a good listener, showing genuine interest, and staying present during the conversation is what really helps you build connection.
It’s never a good idea to talk about past relationships on a date. I have actually ended relationships because there was too much talk of past relationships. This is a time for a new beginning, burn those old bridges.
So whether this first date leads to a second, or it’s just a fun night out, go in with an open heart, a sense of humor, and a few of these questions in your back pocket. You’ve got this.
Laugh and enjoy each other’s company
Always,
Kerri
