If you feel burned out on coming up with questions for a first date, you’re not alone! The ritual of first dates can often feel repetitive and lackluster. There are only so many ways to ask a version of so what are your interests? And if you’ve already been chatting too much on the apps or during the lead up to a date (which, for the record, I somewhat advise against unless that’s truly your preference for getting to know someone!), it can be even harder to know what to say on a first date.

But asking questions is important. If you show up to a date and only answer the other person’s question or otherwise only talk about yourself, trust you’re probably about to get roasted in a group chat. No one likes being on a date with someone who takes zero genuine interest in them! There is no perfect roadmap for how to crush a first date, but the number one thing you can do to at least ensure a baseline decent experience is ask your date(s) about themselves! People love to be asked about themselves! But also, if you find yourself on a date who doesn’t reciprocate the curiosity, find a way to wrap it up.

The questions below are designed to inject some life and creativity back into your first date question asking if you’re feeling stuck or stalled in the dating process. You can ask them word for word or use them to riff and come up with your own against-the-grain questions. They’ve been divided into a few categories: chill, pop culture, strange, spicy, and misc. So take what you need and leave what you don’t! I would consider most of these to be just slightly deeper than surface-level but not too deep. But you’d be surprised what you can learn about a person’s priorities, values, and viewpoints by asking a range of different seemingly random questions.

Some include follow-up questions and some have been added since the last time this was published in 2024, so you’re getting even more than 50 prompts for first date conversation! For some of these, you might be wondering what makes them specifically gay. Well, I wrote them and I’m gay. Hope that helps!

Get ready to crush this first date! You’re gonna do great!

This piece was originally published in March 2024 and has been updated for September 2025.

Chill Questions

These are casual, get-to-know-you questions that are at least slightly more interesting than the general/obvious ones like “what do you do?” Start with these if you want to ease into deeper conversation or if you like to generally take a more chill approach on first dates.

1. How did you meet your best friend?
2. What’s your favorite book?
3. What are your favorite things to do on your days off?
4. What did you do today before this date?
5. What was the last thing that made you laugh?
6. What kind of cake do you like to have for your birthday? Or if not cake, what do you like to have?
7. Do you collect anything?
8. What are your favorite qualities in other people?
9. What’s your favorite photo of yourself?
10. Do you keep a journal?
11. Where have you never been to that you’d like to go?

Pop Culture Questions

Books, movies, television, music, etc. tend to be pretty fun and easy topics for first dates! Here are some pop culture-themed questions you can ask to get to know your date’s interests and tastes!

1. Who is your celebrity crush? Who was your first queer celebrity crush?
2. What album could you listen to on repeat for an entire day?
3. What’s the first gay kiss you can remember seeing in a movie or on television?
4. What’s your go-to karaoke song?
5. What’s a gay movie you know is “bad” but you love anyway?
6. What queer book that hasn’t been made into a series/movie yet do you think should be made into a series/movie?
7. What queer actor should play you in a biopic about your life?
8. What’s an unpopular opinion you have about a piece of queer pop culture?
9. If your life were a television show, what would be the theme song?
10. How many films from the Autostraddle Encyclopedia of Lesbian Cinema have you seen? (This question provides a built-in activity! You can scroll through the list together! And also make plans to watch some movies together!)
11. Who would you want to play you in a movie about your life? Who would you want to direct the movie about your life?

Strange Questions

Want to be memorable? Want your date to think you’re creative and surprising? Ask some of these hyperspecific, open-ended, or just downright weird (in a fun way) questions! Treat your date conversation like a creative writing prompt!

1. Have you ever seen a ghost or experienced a haunting?
2. Do you have any stories about cryptids?
3. What are your thoughts on time travel? If there were zero consequences to the current timeline, would you rather time travel to the past or the future?
4. Do you have any weird stories about birds?
5. If you were a piece of furniture, what would you be?
6. If you had a pet sloth, what would you name it?
7. What do you imagine the bottom of the deepest part of the ocean looks like? (Here’s another activity question: Have them draw it! Doesn’t matter if they’re bad at drawing, that almost makes it more fun.)
8. Do you own any cursed artifacts?
9. Who’s your nemesis?
10. In a fantasy town designed by you, what types of businesses and spaces would be on the main street? (ex. bowling alley, seafood restaurant, independent bookstore, etc.)
11. Fast zombies or slow zombies?

Spicy Questions

Listen, some of us like to jump right to the sexy chase on a first date. If that’s you and your date also gives off a vibe of talking about sex openly, add a little spice to the convo with these questions.

1. What was the last sex dream you had?
2. What’s the weirdest sex dream you’ve had?
3. What’s your favorite non-Hitachi sex toy?
4. What do you think is your sexiest quality?
5. What’s something sexual you’ve always wanted to try but haven’t?
6. Where’s the weirdest place you’ve had sex?
7. What’s a recurring fantasy you have?
8. What songs turn you on?
9. What’s your favorite sex scene from a movie?
10. Have you ever crushed on someone you shouldn’t have?
11. Do you have any favorite rom-com tropes?

Miscellaneous Questions

These first date questions don’t necessarily fit into any of the categories above! They might not be openers like the chill questions, but they could work once you’re a few questions in.

1. Can you remember any of your dreams from last night and if so what were they about? (Or, what’s the last dream you can remember?)
2. What’s the worst first date you’ve ever been on?
3. What’s the best first date you’ve ever been on (other than this one)?
4. How did you decide what to wear to this date?
5. Do you read tarot?
6. What are your thoughts on astrology?
7. What’s your favorite thing about yourself?
8. What’s the worst gift you’ve ever received?
9. What’s the biggest misconception about you?
10. How do you organize your bookshelves?
11. What’s something you’ve lost that you’re still upset about?

Have a good go-to first date question that often leads to a second date? Let’s hear it in the comments.

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!

Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, fiction, and pop culture criticism living in Orlando. She is the former managing editor of TriQuarterly, and her short stories appear in McSweeney’s Quarterly Concern, Joyland, Catapult, The Offing, The Rumpus, Cake Zine, and more. Some of her pop culture writing can be found at The AV Club, Vulture, The Cut, and others. When she is not writing, editing, or reading, she is probably playing tennis. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 1082 articles for us.

How to Make Sure You Have a Perfect First Date

Dating can be incredibly exciting, particularly the first date. It is a lot like setting out on an exciting journey and having no idea where it is going to end up! Consequently, it can also be a little daunting and we know those pre date butterflies can sometimes put you off your A-Game! But relax, we have the top tips to take the stress out of dating and enable you to relax and have some fun!

Keep It Real

We understand that you will be eager to present the very best version of yourself, but we also urge you to keep it real! Making an effort is laudable, so be on time, dress up and be polite…but don’t be tempted to change your personality in an attempt to impress! You’re great as you are, so just be…And whilst it is good to be confident about your attributes, take care not to be self indulgent! Being interested in the other person will give off good vibes and enable you to discover their best attributes.

Leave the past where it belongs…

Hopefully you will recognise that you are at the start of a new journey, not ending an old one. Therefore don’t see this as your opportunity to vent about a previous relationship that went sour. Furthermore, you don’t need to know all the details of your date’s relationship history. Enjoy the art of conversation, this is not an interview. Relax and have fun, you may not see the person again…but at least you can enjoy the moment.

Questions are the source of all knowledge…

Yes, we stated that a date is not an interview, but questions are the key to enabling conversations. Great questions relate to travel, hobbies, films or books! It seems cliched but these trinkets of information can give you an insight into a person’s life and whether you share similar values.

Real life Dating vs Free Online Dating

Are you better at interfacing digitally rather than physically? It is a common problem, swiping this way or that is easy, but offline dating requires a little more social etiquette. Mai Tai Dating urges you to slow down the pace, beauty is more than skin deep so take some time to really get to know the person. At Mai Tai our matchmakers work hard to ensure you are not left feeling underwhelmed and for your peace of mind, all members have verified ID, which means you should only meet with like-minded professional people.

Happy Dating xxxxx

SIGN-UP NOW

Does what you wear really matter? 

We are often urged not to judge a book by its cover or repeatedly told that beauty is only skin deep, so does what we choose to wear on a first date really matter?

The answer is yes! The way you present yourself is probably more powerful than what you say, your image is your personal branding. As you approach your date before you even speak, your outfit is giving out messages and you want to ensure they are receiving the right ones.

Let’s be clear, we are not talking about wearing specific labels or subscribing to the newest trends, that is a more personal choice. However, an outfit which is well put together and fits both your figure and the occasion, is likely to help you to feel good, which will, in turn, give you confidence and confidence is far sexier than a tight-fitting little black number. And this includes the guys, we know you have been squatting and squeezing…but too tight is too much! 

What colour should you wear on a first date?

If you have been crushing on this person for ages, you won’t want to leave anything to chance and ensuring you wear a flattering colour is key. One colour does not fit all, your hair, eyes and skin colour should help you determine what suits you most. So take your time and maybe ask the advice of others.

Do you know how powerful colour choices are? What is yours saying about you?

Blue – Baby blue and pastel shades are soothing and friendly. Electric blue gives off a dynamic vibe.

Red – Drama, assertiveness, passion and strength! Are you a force to be reckoned with?

Green – Practical, nurturing and a love of nature…

How does the fit and appearance of clothing make an impact on a date?

Do you know what body shape you have? Of course, you can always lose a few pounds here and there, but your actual shape remains the same. Having a good understanding of your shape will enable you to buy clothes which flatter you the most. You also need to remain true to your sense of style. If you are naturally a hipster or indulge in boho chic, stick with it. Going all Sloaney in a bid to impress will take you out of your comfort zone and you won’t present the real and best version of yourself. 

Anything else?

When feeling unsure opt for black, better to be overdressed than under dressed and never go too heavy with eyeliner…men included!

Many of us have experienced that butterfly inducing first date. Planning what to wear and eager to create a great first impression, because who knows, this could be the first day of the rest of your life!

This blog highlights the importance of second dates in the world of swiping and liking your way to a life partner. Yes, first dates can be the beginning of something wonderful and the excitement is real!  However, take care not to get swept away in the imagination of some hypothetical future. Remember that a first date rarely tells you what you really need to know about the other person.

First Dates Are So Exciting

For example, we’ve all dated the person who has truly honed their game when it comes to first dates, but that’s because practice makes perfect- and that is not always a good thing. It’s likely they are the person to keep you waiting by the phone, ready to make plans only to find your enthusiasm unrequited and faced with a long evening of a box set marathon.

It is easy to get dazzled! Glinting chandeliers, shimmery cocktail dresses and sparkling champagne, but eventually, that fizz tends to go flat. The vibe, that energy, the butterflies…it’s crazy, stupid, love…right? No wrong!

Remember, the flame that burns twice as bright burns half as long. Being bowled over by first impressions does not necessarily mean longevity. So unless your first date is a complete disaster (and we mean DISASTER) then you need to be prepared to give it a second chance.

Second Dates Are Better

When birds begin courtship in the wild, it is all about flashing those fancy feathers! In the human world, any preening of plumage takes place on the first date, so when it comes to the second date…things need to change gear. 

When you meet up for the second time – no not a dinner date! It’s tried, tested and let’s face it…. you’ve probably ticked that box already. Equally, forget sporting and music events, noisy cocktail bars and anywhere which stops the conversation from flowing.

Add a little soul to your date by hosting at your favourite beauty spot! Or think outside the box and head for a street food market, a boat ride or a cooking class! Sharing an activity together can take away the nerves and the need to impress and really allow personalities to shine through.

Don’t over think it, creating anything too spectacular piles unnecessary pressure on both of you.

Ban the banter! Time to have a conversation…

Try to remember one key thing that you learnt about the other person on your first date. It could be about where they used to live, their ambitions or about their job. Remembering a small detail about something they already told you is not only flattering but also opens up further conversation so you really start to get to know the person.

Be the best version of yourself!

If we kept all the rules which have been written about dating, there would be no space to have any fun….and dating should always be about the fun.

Whilst you may be eager to win over your date, it is important to keep it real. Allow your personality to shine through or you run the risk of seeming fake. You can’t be everything to all people, but you can be everything to that special someone.

We wish you the very best of luck! And finally remember, it’s not about the first date, the first kiss or the first love….it is all about the last one!

Dating can be incredibly exciting, particularly the first date. It’s a lot like setting out on an exciting journey and having and having no idea where it is going to end up!

Consequently, it can also be a little daunting and we know those pre-date butterflies can sometimes put you off your A-Game! But relax, we have the top tips to take the stress out of dating and enable you to relax and have some fun!

Keep It Real

We understand that you will be eager to present the very best version of yourself, but we also urge you to keep it real! Making an effort is laudable, so be on time, dress up and be polite…but don’t be tempted to change your personality in an attempt to impress! You’re great as you are, so just be…And whilst it is good to be confident about your attributes, take care not to be self-indulgent! Being interested in the other person will give off good vibes and enable you to discover their best attributes.

Leave the past where it belongs…

Hopefully, you will recognise that you are at the start of a new journey, not ending an old one. Therefore, don’t see this as your opportunity to vent about a previous relationship that went sour. Furthermore, you don’t need to know all the details of your date’s relationship history. Enjoy the art of conversation, this is not an interview. Relax and have fun, you may not see the person again…but at least you can enjoy the moment.

Questions are the source of all knowledge…

Yes, we stated that a date is not an interview, but questions are the key to enabling conversations. Great questions relate to travel, hobbies, films or books! It seems cliched but these trinkets of information can give you an insight into a person’s life and whether you share similar values.

Real-life Dating vs Free Online Dating

Are you better at interfacing digitally rather than physically? It is a common problem, swiping this way or that is easy, but offline dating requires a little more social etiquette. Mai Tai urges you to slow down the pace, beauty is more than skin deep so take some time to really get to know the person. At Mai Tai, our matchmakers work hard to ensure you are not left feeling underwhelmed and for your peace of mind, all members have been verified, which means you should only meet with like-minded professional people

Let us know how your first date goes Xx