If a guy asks if you are wearing anything, he is almost definitely flirting and hoping you will flirt back.
This is not usually a serious question about your bedtime wardrobe.
You are texting.
It is late.
The conversation gets a little more playful.
Then:
Are you wearing anything?
And suddenly you are staring at your phone like, well, someone got brave.
What you say next depends entirely on whether you like him, want to tease him, want to keep things cute without getting too personal, or would really prefer that he calm down.
The nice part is that you do not have to give him an actual answer.
In fact, some of the best replies tell him almost nothing.
If you like him and want to flirt back
You do not need to write a paragraph.
A little mystery usually works better.
Try:
Wouldn’t you like to know?
Or:
That information is classified.
Or:
You are getting very curious tonight.
Or:
Maybe.
That last one is almost annoyingly effective because it gives him absolutely nothing while somehow keeping the whole conversation alive.
He will probably ask again.
You can continue enjoying your power.
If you want to be a little bolder
Maybe the flirting has already been going on for a while.
You like him.
He knows you like him.
Nobody here is pretending this is a conversation about pajamas anymore.
Try:
What are you hoping I say?
That puts him on the spot.
Now he has to reveal where his mind was going instead of making you do all the work.
Or:
Why? Are you trying to picture me?
If he was feeling confident before, this may suddenly make him much less articulate.
Which can be fun.
If you want a funny answer
Humor is perfect when you want to keep the vibe flirty without actually telling him anything personal.
Try:
Yes. A very glamorous old T shirt.
Or:
Obviously. I am not answering the door naked if the pizza guy arrives.
Or:
Socks. Very mysterious socks.
Or:
A full suit of armor.
Or:
Enough to disappoint you.
That last one is particularly good if he is getting a little too confident.
The beauty of a funny answer is that you get to keep talking without feeling like you have handed over information you never planned to share.
If you want him to admit he is flirting
Sometimes the best response is just:
Why are you asking?
Very simple.
Very effective.
Now watch him scramble.
You may get:
No reason.
Sure.
Or:
Just curious.
Naturally.
Or maybe he finally admits:
Because I was thinking about you.
Well, there we are.
Sometimes a guy asks a bold question because he wants you to do the risky part of the flirting.
Make him explain himself.
Much more entertaining.
If you want to tease him a little
Try:
You first.
That usually changes the conversation quickly.
Now he has to answer the exact question he just threw at you.
Or:
Is this your smoothest line?
Or:
Do you ask every girl that?
That one can be playful if you say it lightly.
If he likes you, he may immediately start trying to convince you that no, obviously, he has never asked another woman a single flirty question in his entire life.
Believe what you wish.
If you want to keep it cute but not too spicy
You can flirt without making the conversation more intimate than you want.
Try:
Pajamas. I am very exciting.
Or:
Something comfy.
Or:
Nothing interesting enough for this interrogation.
Or:
I will let you use your imagination.
That last one gives him exactly enough to keep smiling at his phone without you having to say anything else.
You still control the level of the conversation.
That matters.
If you do not want to answer
Then do not.
You do not need an excuse.
Try:
I am keeping that to myself.
Or:
Nice try.
Or:
Not answering that one.
Or simply change the subject.
If he is normal, he will understand.
If he keeps asking after you clearly did not want to answer, that is when the flirting stops being cute.
A playful question is only playful when you are enjoying it too.
If he asks really early after matching with you
This is where I would pay attention.
You have exchanged twelve messages.
He knows your first name.
Maybe your job.
Possibly your dog’s name.
And somehow he is already asking whether you are wearing anything.
That tells you something.
Maybe you are fine with the flirting.
Great.
But if you are looking for an actual date, do not let a guy skip straight to intimate conversation while somehow never managing to suggest meeting you.
You can say:
You haven’t even asked me out yet and you are already asking that?
That is playful, but it also makes your point.
Now see what he does.
A guy who genuinely wants to date you has been handed a very easy opening.
If he says “Are you in bed?”
This is often how it starts.
Are you in bed?
You answer yes.
Then:
Are you wearing anything?
Ah.
We have arrived.
If you want to flirt:
Maybe. Why?
If you want to keep things lighter:
Yes, and that is all the information you are getting.
If you are not interested:
You are getting a little too personal.
You do not have to keep following the conversation just because he successfully led it there.
If he asks what you are wearing instead
Same basic idea.
You can answer honestly if you want.
You can also say:
Guess.
That will probably occupy him for a while.
Or:
Something very boring.
Or:
Why are you so interested?
If he is trying to flirt, he will probably make that pretty clear in the next message.
And honestly, sometimes watching a guy talk himself into admitting his intentions is half the fun.
The best response if you really like him
If there is already strong chemistry and you want to make it obvious you are into him too:
Maybe you will find out one day.
That is flirty without promising anything.
It also moves the conversation away from giving him details right now and toward the possibility of actually seeing each other.
Which is where I would rather this go anyway.
Because texting chemistry is lovely.
Actual dates are much more useful.
If he only asks this stuff late at night
Notice that.
You barely hear from him all day.
Then midnight arrives and suddenly he becomes a poet.
He wants to know what you are wearing.
Whether you are in bed.
Whether you miss him.
Whether you are thinking about him.
Then morning comes and apparently he has lost access to his phone.
That pattern matters more than one flirty question.
A guy can absolutely like you and flirt at night.
But if nighttime is the only time he seems interested, I would not automatically treat those conversations like evidence of something serious.
See if he can make plans while the sun is out.
If he likes you, the flirting should not be the whole relationship
You want someone who can ask:
What are you wearing?
and also:
How did your meeting go?
You want the guy who can flirt with you at night and remember your coffee order in the morning.
Someone who thinks you are attractive and also actually wants to know you.
That combination is much better than a man who becomes fascinating at 11:45 PM and nearly impossible to locate by lunch.
What if you want him to stop asking questions like this?
Be clear.
You can say:
I like talking to you, but I am not really into questions like that.
That is completely reasonable.
You do not have to make yourself uncomfortable because you worry he will think you are boring.
If he loses interest the second you set one small boundary, he probably was not bringing much to the situation anyway.
A guy who actually likes you can survive not knowing what you are wearing to bed tonight.
I promise.
What if you already sent a flirty answer and regret it?
Nothing terrible has happened.
You are allowed to change the tone whenever you want.
Maybe you were having fun and then the conversation went further than you expected.
Just slow it down.
Change the subject.
Or say:
Okay, that is enough trouble for tonight.
Cute.
Clear.
Done.
You never have to keep going just because you started flirting.
If he says “prove it”
You do not owe him proof of anything.
Not a picture.
Not more details.
Nothing.
You can say:
Absolutely not.
Or:
Nice try.
Or:
Your imagination will have to work overtime.
If he gets annoyed, that tells you plenty.
A guy who cannot handle a playful no is not suddenly going to become more charming when the stakes are higher.
If you want to turn it into an actual date
This is my favorite move if you genuinely like him.
He asks:
Are you wearing anything?
You say:
Ask me over dinner Friday.
Now we are getting somewhere.
You just took a late night text flirtation and handed him the easiest possible opportunity to make a real plan.
If he likes you, he can use it.
If he ignores the date part and keeps pushing the same conversation, you have learned something useful too.
Do not overthink whether the question means he likes you
It means he is probably attracted to you.
That part is fairly easy.
Whether he actually likes you is a bigger question.
Look at what he does the rest of the time.
Does he text when he is not bored in bed?
Does he make plans?
Does he show up?
Does he ask questions that have nothing to do with what you are wearing?
Does he remember things?
Does he make you feel like a girl he wants to know or merely a girl he wants to flirt with?
There is your answer.
So what should you say when a guy asks if you are wearing anything?
If you like him and want to flirt:
Wouldn’t you like to know?
If you want to tease him:
Why? Are you picturing me?
If you want to be funny:
A full suit of armor.
If you want to keep some mystery:
I will let you use your imagination.
If you want him to take you on an actual date:
Ask me over dinner Friday.
And if you do not want to answer:
I am keeping that to myself.
Honestly, that is the whole game.
You do not need the perfect line.
You just need a reply that matches how you actually feel.
Because a guy asking if you are wearing anything is probably trying to turn up the flirting.
Whether the conversation gets any hotter from there is entirely up to you.
