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.
Sep 19, 2023
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?
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:
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.
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!
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.
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.
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.
Too early for embarrassing pee or poop jokes? Never!
Another tried and true gay classic. Feel free to include the cast of Gen Q as well.
Source: IMDb
Or are you straight?
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.
A karaoke bar is always a great lesbian second date idea.
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.
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!
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.
The age old debate! Which side of TikTok are you on?
Source: Sydney Morning Herald
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?
Before you get to the actual spooning, it’s good to know what you’re working with!
What bad song do you absolutely go insane for when you’re alone in your room with the speakers on full blast?
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 know what your dog or cat was saying or be able to travel effortlessly without using Google translate? The choice is yours.
And if your date answers the second one, the real question is which one?
No shame. Genuine question.
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?
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!
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?
And no, bringing your smartphone is not allowed!!
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?
This also might be a fun time to start planning couples costumes for next Halloween…
You could choose any animal to tame and be your BFF. What animal would you want?
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!
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
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!
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.
