Awkward Questions to Ask a Girl
These 50 awkward questions to ask a girl are for anyone who is texting her, dating her or already her boyfriend, and who wants her laughing with her hands over her face and not looking for the door. They run from mild to extremely awkward in six groups: Mild, Cringe stories, Her flaws, Crushes and exes, About me and Extremely awkward. All of them are clean, and the About me group turns the awkwardness around on whoever is asking.
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The questions
Each question, and why to ask it
Mild
What's the most awkward thing that's happened to you this month?
Why ask it
Keeping it to this month rules out the story she has polished for years and gets you something small and fresh, like a 'love you' said to a delivery driver. If she can't think of one, tell her yours and hers tends to come back to her.
What's the worst haircut you've ever had, and who still has the photo?
Why ask it
A safe early squirm, since the haircut is long gone and the photo is the real prize. If she is the one who still has it and shows you, you owe her your own worst one before you say a word about hers.
What have you been pronouncing wrong for years before somebody finally corrected you?
Why ask it
It is usually a word she met in a book long before she heard anyone say it. Offer yours first, and don't correct her if she says it wrong again while telling the story.
Who was the last person you pretended not to see in public, and what did you stare at instead?
Why ask it
The comedy is in the cover: a cereal box read like a novel, a shop window she had no reason to study. Ask who the person was only if she offers it, because the reason for hiding can be a longer story than the hiding.
What's the silliest thing you've ever cried over?
Why ask it
The word 'silliest' is doing the work: you are asking about the commercial with the old dog, not about a bad year. Laugh with the story, never at the crying, and if what comes out is not silly at all, the game pauses and you listen.
How long has the oldest unanswered message in your phone been sitting there, and who is it from?
Why ask it
She has to open her phone and count, and the guilty party is usually an aunt or a dentist's office. It gets awkward only if the neglected message is yours, in which case let her squirm for a second and then let it go.
What were you a superfan of that you now deny, and how far did it go?
Why ask it
'How far' is where the awkward lives: a fan account, a bedroom wall, a username she still has to log in with. Ask for the username, and don't pretend you never had a phase of your own.
Do you talk to yourself out loud, and what was the last conversation about?
Why ask it
Asking about the last conversation is what stops her from just saying yes. If she narrates her cooking or rehearses arguments in the shower, say you like knowing that, and leave the word 'weird' out of it.
Cringe stories
Have you ever waved back at someone who was waving at the person behind you, and what did you do with your hand?
Why ask it
Hard to deny, so skip past the yes or no and go straight to the cover-up: the fake hair fix, the stretch, the wave that turned into a head scratch. Act out yours.
What's the most awkward hug, handshake or goodbye you've ever been part of?
Why ask it
If the two of you had one of these the first time you met, the hug that met a handshake or the goodbye followed by walking off in the same direction, this is her chance to bring it up. Be ready to laugh at yourself.
What's the most embarrassing thing a parent has done in front of your friends or a date?
Why ask it
She gets to tell an embarrassing story where somebody else is to blame, which makes it an easy one early in this group. Don't pile on her mom or dad, though: she is allowed to laugh at them and you are not yet.
What's the worst 'you too' you've ever blurted out, like to a waiter who said 'enjoy your meal'?
Why ask it
A two-word mistake that can still make someone wince years later. Ask whether she corrected herself or just kept walking, then confess yours: 'happy birthday' answered with 'you too' is hard to beat.
Have you ever had a whole conversation with someone whose name you'd forgotten, and how did it end?
Why ask it
Listen for her escape trick, like handing over her phone so they type their own contact, or introducing a friend and waiting. If she goes suddenly quiet, check that she knows your last name.
What's the worst first impression you've ever made on someone?
Why ask it
The follow-up is whether that person ever changed their mind about her, which turns a wince into a story with an ending. Save the first impression she made on you until she asks for it.
When did you last trip, spill something or walk into a door in front of someone you wanted to impress?
Why ask it
The 'someone you wanted to impress' part is what makes her blush, since she has to say who. If the someone was you, don't gloat. Tell her you didn't notice, or that you did and liked her better for it.
What's the most embarrassing thing sitting in your notes app or drafts right now?
Why ask it
She decides how much to read out, and you never reach for the phone. A summary counts as a full answer, whether it is song lyrics or a text she wrote and never sent.
Her flaws
What's your most annoying habit, according to the people who live with you?
Why ask it
Putting it in her family's or roommates' mouths makes it easier to say and more likely to be true. Whatever it is, hair in the drain or every light left on, the only correct reply is an annoying habit of your own.
How long do you really take to get ready, and what number do you tell people?
Why ask it
The gap between the two numbers is the joke. Fair with almost anyone as long as it stays about the clock and never slides into comments on how she looks at the end of it.
What are you such a sore loser about that people have stopped playing with you?
Why ask it
If she names the game with pride, you have a date idea: mini golf, a board game, whatever it was. Go in knowing that you will either lose or meet the sore loser in person.
What do you turn into when you're hungry or short on sleep, and how much warning do people get?
Why ask it
Useful as well as awkward. Take the answer as instructions and not as ammunition: if she says she goes silent and snappy, the move later is a snack, not a reminder that she warned you.
When you're wrong, do you say sorry out loud or just start being extra nice?
Why ask it
Two options let her pick one without confessing to anything worse, and the extra-nice route is the easy one to admit. Don't ask this during or right after a disagreement, when it lands as a dig.
Which white lie do you tell most: 'on my way,' 'I'm fine' or 'I just saw your message'?
Why ask it
Two of the three could have been told to you, which is why she will take a second before choosing. If she picks 'I'm fine,' ask what the giveaway is so you can spot it next time, and don't go back through old conversations hunting for one.
What would your best friend say is the hardest part of being your friend?
Why ask it
This is the flaw question with a cushion, since she is quoting someone who loves her anyway. Expect 'I'm always late' or 'I cancel plans.' If she gives a heavier answer, thank her for it and move back up the page.
Crushes and exes
What did you see in your first crush that you can't explain now?
Why ask it
Old crushes are embarrassing in a gentle way, which makes this the place to start the group. If she still has the reasons memorized, like his skateboard or his handwriting, let her list every one.
On a scale of one to ten, how awkward was your first kiss?
Why ask it
The number lets her answer without telling the whole story, and bumped noses or braces are there if she wants to add them. If she hasn't had one or would rather not say, that is a pass like any other, so move on without a comment.
What's the most awkward way anyone has ever asked you out?
Why ask it
She might tell it kindly or as a joke at the guy's expense, and that difference is worth noticing. Expect a note passed through three friends, or a text that just said 'so.'
What's the worst date you've ever sat through, and at what minute did you know?
Why ask it
The 'what minute' makes her pin down the exact moment: the third story about his ex, the phone face up on the table. Don't ask whether tonight is in the running unless you want the answer.
What's the smallest thing that ever gave you the ick about someone you liked?
Why ask it
The answers are gloriously unfair: the way he ran for a bus, how he held a fork. Enjoy the story and resist checking yourself against it out loud.
Have you ever had a crush on a friend's brother or a friend's ex, and did the friend find out?
Why ask it
The crush is the easy half, and whether the friend knows is the part that makes her lower her voice. If it is someone you both know, the name stays with you, and that includes not grinning the next time you are all in one room.
Do your exes or old crushes have code names in your friend group, and what are they?
Why ask it
The names are rarely flattering, and she may hold a few back, which is fine. The awkward follow-up is whether you have one yet, so ask only if you can take hearing it.
Have you ever turned someone down badly, and what would you say if you got a second try?
Why ask it
Here she is the one who caused the awkwardness, so go easy if she clearly still feels bad about it. Her second-try line is worth remembering, since it is probably close to how she would want to hear a no herself.
What would your last ex say was the most annoying thing about dating you?
Why ask it
Fair once you have been on a few dates, too much before the first. She has to argue the other side's case, and a joke is the usual way out. Don't ask who was right, and don't ask for the ex's name.
Have you ever looked up an ex's new girlfriend, and what were you checking for?
Why ask it
A quick yes is an ordinary answer and nothing to read into, so stay amused. If the ex in question is recent and the subject still stings, leave the second half unasked.
About me
What was your first impression of me, in three words you were too polite to say?
Why ask it
The three-word limit keeps it short enough to survive. Take whatever comes, 'loud,' 'nervous,' 'trying hard,' with a laugh, and then give her your three about her, chosen kindly.
How am I saved in your phone, and has it ever been something else?
Why ask it
A first name plus where you met is normal and not an insult. If she turns the screen away laughing, that is good news. You show yours as well, so check what it says before you ask.
Did you look me up before we met, and how far back did you scroll?
Why ask it
Say first how far back you went on hers, which makes it a shared crime. Then ask which old photo of yours she wishes she could unsee.
When did you first figure out that I liked you, and how obvious was I being?
Why ask it
Only for a girl who already knows you like her, since otherwise the question is the announcement. The awkwardness lands on you here, which is fair after a page of putting her on the spot.
Have you ever screenshotted one of my messages and sent it to a friend, and which one?
Why ask it
Getting a second opinion from friends is ordinary, so the yes isn't the embarrassing part. Which message is. Don't ask to see the friend's reply: that conversation was not meant for you.
When was the last time you laughed at one of my jokes just to be nice?
Why ask it
She will either deny it too fast or name the exact joke, and both are funny. Ask this only if you can retire the joke gracefully, because defending it makes things worse.
What's the worst thing I've worn around you so far?
Why ask it
A question about your clothes, never hers. If she has an answer ready before you finish the sentence, wear it once more on purpose and then take the hint.
Am I better over text or in person, and by how much?
Why ask it
One of the two is going to sting a little, and that is the point. If she says text, take it as a nudge to relax face to face. If she says in person, your messages may be working too hard.
What habit of mine would you fix first if I handed you one free edit?
Why ask it
One edit keeps it from becoming a list. You asked, so you don't get to argue or sulk, and 'noted' is the whole reply. Leave it out on a night when you already know you can't hear the answer.
Extremely awkward
Is this a date, or have I been reading it wrong?
Why ask it
The most awkward question on the page and often the most useful. Ask it once, plainly, and take the answer as final. If it is a no, thank her for being straight with you and stay friendly.
Is there anyone else in the picture right now, and would you tell me if there were?
Why ask it
Before the two of you have agreed to anything, a yes is not a betrayal, so don't treat it as one. You are asking for a straight answer and you owe one back. Be sure you want to know before you ask.
Am I texting you more than you'd like, or less?
Why ask it
Awkward to ask and a relief to have answered. She may say 'it's fine' to be polite, so notice whether she picks a side. Then change the habit, because asking and carrying on as before is worse than not asking.
What do your parents think of the people you've liked so far, and what would they make of me?
Why ask it
The first half is stories, and the second half makes her picture you at her family's table. That is a lot for a first date and fair after a month or two. A long pause before she answers is thinking, so don't fill it.
What do you think the two of us would argue about most?
Why ask it
It asks her to name a difference between you that she has already noticed: being late, how much each of you plans, who picks the music. Guess what she will say before she says it and see how close you get.
What do you usually keep hidden from someone until you're sure they're staying around?
Why ask it
For a girlfriend or someone close to it, in private, with time to spare. She may answer with something small, like a messy room or a comfort show she has seen nine times, and that counts. Whatever it is, it never comes back as a joke.
What have you wanted to ask me and kept talking yourself out of?
Why ask it
This hands her the list for one turn, and her question may be harder than anything you asked. Answer it straight. Dodging now, after everything you have put to her, tells her the game only runs one way.
Which of these did you only half answer, and do you want another try at it?
Why ask it
A soft way to finish, because she chooses what to reopen. If she says none, believe her and close with the one you only half answered yourself.
How to ask an awkward question and still be someone she wants to talk to
Practical guidance for the conversation itself
Getting her in on the joke
Ask before you ask
Open with something like 'I found a list of awkward questions, want to trade a few?' A question about her exes that arrives with no warning sounds like you are checking up on her. The same one inside a game she said yes to is just her turn.
Whatever she answers, you answer
Every question on the page can be turned around, and most of the About me group lands on you by design. Give your answer at the same size as hers. If there is one you would refuse to answer yourself, leave it out.
Skips cost nothing
Tell her at the start that 'pass' is a complete answer and needs no reason. Don't count her skips, don't guess at what is behind them, and don't offer a skip as a trade for a harder question.
Text or in person
Mild and Cringe stories work well over text, where she has time to pick the story and dig out the photo. From Crushes and exes on, ask in person or on a call: typed out, a teasing question loses its tone, and a long gap before her reply will have you imagining the worst.
How far down the page to go
You've only just started talking
Stay in Mild and Cringe stories. Nothing there asks about the two of you or about anyone she has dated, so nothing can be read as a move or a test. Two or three in one conversation is plenty.
A few dates in
Her flaws and the lighter half of Crushes and exes are fair now: the first crush, the first kiss, the bad date. About me opens up once it is clear to both of you that these are dates.
She's your girlfriend
The whole page is open, and most of Extremely awkward was written for the two of you. You also have the most to lose by asking carelessly, so pick a calm evening and not the tail end of an argument.
With other people around
Only the first two groups survive an audience. Asking a girl about her exes or what she thinks of you in front of friends turns a game into a performance, and she will give the safe answer or none.
Fun awkward or actually uncomfortable
What good squirming looks like
She covers her face, laughs, says 'I can't believe I'm telling you this' and then tells you. She fires the question straight back. Her answers get longer as the list goes on.
What a real no looks like
Answers shrink to a word or two, she checks her phone or changes the subject, the laugh goes flat, or she says 'why do you want to know?' without smiling. Over text it is a reply that takes much longer and says much less.
The ten-second exit
'Fair, that one's retired' is all it takes, followed by an easier question or your own embarrassing answer. Don't explain what you meant, and keep any apology to a few words so she doesn't end up comforting you.
A pass stays passed
A question she skipped does not come back later in the evening in different words, and it does not come back next week. If she wants to answer it someday, she knows where to find you.
After she has answered
Her stories stay with you
The haircut photo, the code names, the first-kiss score: none of it gets retold to your friends or posted anywhere. One story repeated to the wrong person and she will never play again, with good reason.
Game answers stay out of arguments
If she told you she is a sore loser or which white lie she leans on, that is off the table in a real disagreement. Using a game answer to win an argument teaches her to answer less next time.
What this page leaves out
There is nothing here about her body, her weight, her looks or her sexual history, and nothing that asks her to rank herself against other girls. Those are not awkward in a fun way, and improvising in that direction is how the game ends early.
Stop while it's still funny
Four or five questions in a sitting is a good evening. Finish on one from Mild, or on the last question in the list, so that what she remembers is the laughing and not the hardest one.