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How to break the ice: +35 funny first date questions to win your crush over

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Sep 19, 2023

How to break the ice: +35 funny first date questions to win your crush over
  • First dates can be a lot. Whether you are an online dating pro or you’ve just got back on the lesbian dating apps after a long hiatus, you might still get those pre-first date jitters.

     First dates can be stressful! What to wear? What to talk about? How do you make a good first impression with that promising cutie you matched with? You’re probably racking your brain for ways to make your date laugh, especially if they are a certified hottie. 

    Don’t worry. It’s normal to be nervous when meeting up with someone for the first time, especially if you’re hoping to hit it off! It can be hard to keep the conversation flowing, steer clear of awkward moments, and think of funny first date questions all at the same time. If only there was an article with a heavily researched list of icebreakers and hilarious questions to ask on a first date with a new girl … oh wait. 

    See what I did there?


    First date icebreakers

    Before you bust out your best stand-up jokes, you want to make sure that you two have covered some of the conversational bases first. Try to strike that balance between being funny while showing that you are interested in their life. While it’s always a plus to be able to make a date laugh, you don’t necessarily want to jump straight into the banter without getting to know each other first. 

    Or maybe you’re not really looking for a list of funny date questions so much as you just want to break the first date ice. Not all of us can be effortlessly hilarious, and that’s okay! Know your strengths. How do you have a fun conversation on a date?

    Here are just a couple of fun dating questions you can start out with to get things going:

    • What is something that you are passionate about? 
    • Who is your best friend? What is something you admire about them?
    • What is something that you would do if money was no object? 
    • Do you have any siblings? 
    • What are your astrological big three—sun, moon, and rising? (A lesbian classic)
    • Are you more of a deep sea or an outer space gay?
    • Are you a city or a nature person?

    If these don’t feel natural, another fun first date icebreaker is always a good old-fashioned game of two truths and a lie. Two truths and a lie is a game where you both say three statements: two that are true and one lie. Then, the other person has to guess what the lie is. This can be a great conversational get-to-know-you game that allows both of you to tell stories about yourself.

    A lesbian couple laughing in the park together after telling some funny first date jokes. One woman is wearing a flannel and the other is in a blue sweater.

    27 funny questions to ask on a first date

    What are some fun questions to ask on a first date you ask? Feel free to write a few of these down and put them in your back pocket, or you can play the 20 question game on a date. The premise is pretty simple. You just create a list of twenty questions (feel free to take some of these from below) and ask your crush one question at a time. Or you can both take turns asking!


    If you could turn one celebrity gay, who would it be? 

    This is a classic queer first date question. You could also try guessing which celebrities are secretly gay, lesbian, or bi but haven’t come out yet. 


    What would you think my name was if you didn’t know it?

    This is always a funny question to ask. You can get them to guess what your name would be if they just saw you at a bar, and you can even talk about nicknames or names that you always wished you had.


    What’s the weirdest first date you’ve ever been on?

    Besides this one of course… No seriously, telling tragic first date stories is a great way to break the awkwardness of a date straight off the bat.


    Have you ever peed in a public pool?

    Too early for embarrassing pee or poop jokes? Never!


    If you were a character from the L Word, who would you be?

    Another tried and true gay classic. Feel free to include the cast of Gen Q as well. 

    The cover photo for the L word Generation Q on a pink background featuring all the characters.

    Source: IMDb


    Are you friends with any of your exes?

    Or are you straight? 


    Do you have any relationship dealbreakers? What are they?

    This can be a lighthearted way to get the juicy gossip out of the way. What are your dealbreakers? Bad breath? Someone who wears toe-shoes? Scorpios? Let them rip. 


    What is your favorite karaoke song?

    A karaoke bar is always a great lesbian second date idea.


    Have you ever been injured during sex?

    Ever knock yourself out on the bedside table while getting fucked? No? Just me? If not, maybe ask your day what their most awkward sexual experience was ever like … not only will this make them laugh, but it will give you some useful information for what NOT to do.


    If you could live in any other country, which country would it be and why?

    This one might not be funny, but we love an international romance! Maybe your date already has dual citizenship or has never traveled abroad, but asking someone what other country they would live in is a great way to get to know them. Add it to the honeymoon list!


    Do you make the first move or do you like it when someone else does?

    This question can be a cheeky way to start some flirty funny banter on a first date. Once you’ve got your answer, then you’ll have a pretty good idea of what to expect next.


    Are you a Gaylor or a Swiftie? 

    The age old debate! Which side of TikTok are you on?

    A picture of Taylor Swift in a pastel rainbow fringe costume with a rainbow behind her. Or is it Gaylor Swift now?

    Source: Sydney Morning Herald


    What would be your role in the zombie apocalypse?

    Are you more of a hunter/gatherer type with a shotgun slung on your back, or would you be the one hiding in the closet rocking back and forth with your eyes shut?


    Are you a big spoon or a little spoon?

    Before you get to the actual spooning, it’s good to know what you’re working with!


    What is your cringiest guilty pleasure song?

    What bad song do you absolutely go insane for when you’re alone in your room with the speakers on full blast?


    What is one weird smell you love that other people don’t?

    Gasoline? The smell of concrete after it rains? Gym socks? This funny first date question is guaranteed to make your date crack up.


    Would you rather be able to converse with animals, or have lifelong fluency in every language?

    Would you rather know what your dog or cat was saying or be able to travel effortlessly without using Google translate? The choice is yours.


    Would you rather all songs exist, but they are all performed by Tegan and Sara, or only one Tegan and Sara song exists, but it’s performed by every artist with their own cover interpretation? 

    And if your date answers the second one, the real question is which one?


    Have you ever sharted? Be honest.

    No shame. Genuine question. 


    Did you have any queer experiences as a kid?

    This is a spin-off of the age-old coming out question and can be fun to relive some of your gay childhood moments. If neither of you had any, was there a teacher or some girl on TV or in your favorite band that you had a crush on?


    Have you ever pranked someone or been pranked?

    I’m personally a huge fan of pranks. Did you ever prank call anyone as a kid or TP someone’s house? Time to pull out all your hi-jinx stories!


    As a kid, what did you want to be when you grew up?

    One of my ex-girlfriends told her mom that she wanted to either be a flight attendant or a prostitute when she grew up. Meanwhile, I wanted to be a photographer for National Geographic. How about you?


    If you could only bring 5 objects with you to a deserted island, what would you bring?

    And no, bringing your smartphone is not allowed!!


    What is something that you find hot that isn’t conventionally attractive?

    This is always a really fun first date question. Are you into big ears? Crooked teeth? Beauty marks? Happy trails? What is one thing that you find super adorable and attractive that no one else does?

    A quirky cute girl with a big afro, crooked teeth, and a mole on her face smiling with her hands on her knees.

    What’s been your best Halloween costume?

    This also might be a fun time to start planning couples costumes for next Halloween…


    If you could have one wild animal as a pet, what would it be?

    You could choose any animal to tame and be your BFF. What animal would you want?


    How would you rate this date on a scale of 1-10?

    This is a great cheeky way to get a vibe on how the date is going. Don’t be afraid to ask what their first impression of you was or call the date itself into question. Nothing like a little bit of flirty banter to get the awkwardness out of the way!


    What are some of the funniest things you’ve been asked on a first date?

    I asked some of my friends what are some of the funniest things that someone has ever asked them on a date. The answers I got were hilarious and mixed. 

    My friend Cíara told me, “I’m from Ireland and the person asked if we have electricity.”

    Cíara

    “They went on a date with a girl who asked if anyone had sucked their toes before.”

    Emilio

    Shann Humphrey, a trans guy from Denver, has been asked, “Wait, how gay are you?”

    Anonymous

    And on another first date, a girl asked him “What would you name your first kid?”

    Anonymous

    “Aaron.”

    responded Shann Humphrey.

    She broke down crying and had a panic attack because her ex was named “Aaron”.

    Megan, from Miami, was once approached at a bar and asked, “Are you a DJ? You seem hot and unstable.”

    Anonymous
    Two lesbian women sitting on a bench on a first date with beers in their hands laughing at funny first date questions.

    How can I turn an awkward date around?

    Like I’ve said before, it’s normal to have a few awkward moments on a first date. It can be hard to meet a complete stranger who you have no context for and to fit seamlessly into each other’s lives right off the bat! If things feel a little awkward, don’t stress it too much. 

    The key to getting comfortable on a first date is being yourself. If you aren’t the funniest person in the world, that’s okay! It’s always good to have a few questions in mind to ask if the conversation isn’t flowing, but you don’t need to memorize a bunch of jokes to make sure that your date finds you funny. 

    While it can be stressful to figure out what you are going to say next on a date on those awkward moments, just make sure that you’re actively listening and paying attention to your date as they speak. This small gesture will go a long way and show them that on top of being funny, you are also emotionally intelligent and truly interested in what they have to say!

    Meeting the right person will feel easy, and they will appreciate your authentic self, no matter what. A great start to a relationship is when you both realize that you share the same weird sense of humor. Whoever is the right person for you will find you cute, charming, and funny regardless of what you do or don’t say!

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    Dusty Brandt Howard is a writer & a fighter. He is a trans masculine cultural narrator who builds worlds with words. You can follow his thirst traps on Instagram, his writing on Substack, or find him at your local queer bar in northeast LA.

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