Dear Boys, What Are You Wearing?

Something She Said

Stories about sex and dating, screenshots of sexist online dating messages, murder jokes, elaborately long fruit puns–you never quite know what you’re going to get.

What are you wearing?  That’s what the message says.  What are you wearing?  That’s what all the messages say, from all the boys, at some time or another, and I haven’t a fucking clue how to respond.  Hell, I’m not even entirely sure it’s a question.  I’m stumped.

 What do you want from me?!?!?!?


When you ask this thing what are you wearing?; when you say these words what are you wearing?; when your message appears across my screen what are you wearing?:  I mean, am I supposed to tell you the literal truth?  Because here’s the thing of the thing.  When you and I are together, when we’re at the stage that I’m ready for you to see the skivvies, oh yeah, I’m wearing the Red Lacies.  The sexy boy shorts.  This illicit thing.  For sure.  But when I’m at home, alone, away from you.  You can be damn sure that I’m wearing my adorable jogging pants.  No they’re not tight, they’re just normal, don’t make this weird.  They’re regular soft and stretchy comfy pants.  So no, I’m not wearing that sexy lingerie you’re dreaming of.  And no, I’m not sauntering around naked.  Don’t be an idiot.  I have shit to do.  Like cooking bacon that splatters.  Or jazzercising in front of open windows.  And that stuff can’t be done naked.    Obvs.

But I mean I get it.  I’m a writer, after all, I can be creative.  I can amp it up for you.  But is that what you want?  Is that really what you’re asking me?  Do you want me to create some verbal fantasy that I think you’ll think is sexy?  Or are you aiming for a realistic picture of how adorable hot I look in real life, at that very moment?  Or is there a third (and forth) possibility?  Are you hoping this will lead to sexting or phone sex?  Or even more hopeful, is this your way of testing the waters of booty call lake, to see if I’m interested in getting wet, in having a quick dip?  I honestly don’t know what your deal is, boys, and thus, here is my plea:

Dear boys,

My dear sweet boys.  What is it exactly that you want from me?  The reality of it all?  Or do you want the smoke and mirrors and pay no attention to that man behind the curtain?  Do you want to be able to picture me in the very way that I am, at that very moment that you message me?  Or is your aim the sugar and sexy spice that comes standard on our date nights?  Are you trying to get into my skivvies?  Is this the time for fantastical fictional narratives?  Honestly, tell me boys, seriously, what the fuck do you want from me when you type those confusing words–What are you wearing?

Yours Truly,

Judgey Wudgey

aka Something She Dated
aka Your favorite jogging pants sexter
aka That girl at the coffee shop
aka flip that bacon girl it’s burning
aka Dating Vancouver a better place one “something” at a time

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Victoria Young

Writer. Dater. Masturbator. Don't worry my parents don't think I'm funny either. Grad Student. My breasts aren't ashamed of me either. You and me kid, we're going to change this world.


  1. catscitylife

    January 12, 2011 at 1:42 pm

    Love! If you get an honest answer to this, let me know, I could definitely use it.

  2. Matt79

    January 12, 2011 at 1:53 pm

    If it were me I’d probably prefer honesty but then try to work with it somehow. There must be something sexy about loose jogging pants – e.g. plenty of room to put your hands down them? I’d try to get creative like that somehow.

  3. Just Sayin

    January 12, 2011 at 2:08 pm

    hahahahahahahahah big breath hahahahahahahaha

    I love you now! That post made my friggin day!

  4. Anonymous

    January 12, 2011 at 5:09 pm


    But I don’t do that.
    I could care less what you’re wearing.

    I’d rather ask, what will you be wearing the next time I see you. So I can attempt to get you to show me some undies (and if you show then i might think your down for a little fun sometime soon)

    Sexting is a waste of mt bundle SMS’s lol, and so is phone sex, waste of my minutes, I can watch a porn vid (in under 15mins) and save a whole 20mins of calling minutes

    Maybe I’m not as sexually active as every other guy on earth.

    But I get mine at least once every 6 weeks, so i really dont stress over it.

  5. Dating A Lemon

    January 12, 2011 at 5:25 pm

    I can only tell you why I do it. There are two reasons and you’ve hit both of them on the head.
    There are some girls who we have a pure flirting/sexting relationship… maybe she’s a booty call, maybe it still hasn’t led to sex – but we may sext/phone sex. Those girls, most of the time when I ask, I’m trying to open the door to phone sex/sexting.

    Then there are the girls I’m dating, really like, dare I say – have loved. With them, I just want to imagine what they look like at that given moment. I’ve probably already seen them w/o makeup, in sweat pants, all gruby, so I know they’re not always wearing lacy thongs. So with them, the what are you wearing is just me trying to imagine them – gruby sweat pants and all – wishing they were there with me…. and maybe I’m hoping it might lead to some sexting/phone sex. 🙂

    Bottom line:
    Booty call girl – only want to open the door to phone sex

    GF – genuinely interested – 2% wanna open the door to phone sex, but then again, most things we say are in hopes of phone sex.

  6. Wingman

    January 12, 2011 at 5:42 pm

    Dating a Lemon hit the nail right on the head. It’s all about context. If it’s someone you’re hooking up with and it’s not serious, you’re not imagining anything else than how you can get her out of what she’s wearing.

    If it’s more serious, it’s about imagining *her.* As cute or as sexy as she is, what she looks like *right now.*

  7. turnjacson

    January 12, 2011 at 5:45 pm

    This is a tough one to decode… Plus it varies depending on the relationship you have with the guy.

    In short, he’s thinking about you (most likely dirty thoughts) but just doesn’t want to send a “Hey, How is it going I was thinking about you so I thought I’d send you a text to see how your doing.” text. Not that guys who send that kind of text doesn’t exist, it’s just not common.

    So we think of a different way to ask how your doing, but we want to make it sound like we aren’t thinking about you at all. (Most guys go out of their way to make it sound like you’ve never crossed their minds)

    I sent a girl a text at New Years saying… “Happy New Years, Your ass is the bomb.”

    Fact: I’m not into this girl at all, I actually kiboshed all hang outs after our 2nd get together
    Fact: I was drunk, I was board, I was flirty, it was a booty call text… so she gets this text thinking “WTF! Mixed signals”

    At the end of the day, guys think with their member more often than not… So if your in a relationship with a guy and he sends that text, be witty back because he’s thinking about you and part of him cares about what your wearing… a strong retort about lace and thongs means your in a good mood and playful ( and it might lead to sex)… texting back that your in sweats watching Gilmore girls and eating a tub of ice cream lets us know a) you aren’t playful right now and b) something is definitely wrong.

    Now if it’s a guy you kinda know but don’t talk to often… he’s most likely board and looking for someone to play with (booty call… tell him to f-off!

    There’s so many different interpretations, this is what I glean from it… I hope I helped a little.

    By the way… What are you wearing? LOL #FTW

  8. Urban Dater

    January 12, 2011 at 5:48 pm

    Oh dear, girl! You need to understand boys a little more, or at least sympathize with our most basic need. Sex. We think about sex every few minutes, it’s amazing we get anything done at all! It’s what drives us to great peaks and valleys in our quest of being more idiotic than the next guy.

    The nature of this question isn’t serious; it’s playful, flirty even. So when responding keep that mind, be flirty and playful back. And, yeah, we know you’re in your sweats as you sit down to watch the latest Vampire Diaries. We get it. On occassion I send this question to my girlfriend when I know she’s teaching 8th graders. I know she’s not wearing anything sexy and probably wearing those ugly ass pumps I hate so much! I’m being playful and flirting. She’s responded to me with: “Oh, just wearing heels today, no skirt or top. The students are not paying attention.” Nice.

    So when we reach out to play, come on out and play with us, too.

  9. Sam Sharpe

    January 12, 2011 at 6:37 pm

    Good question….but not one I think I’ve ever asked, at least not via text….

    Generally, I would interpret the query as a feeler, as an attempt to suss you out. Is she going to play along? Is she going to ignore it or worse shut me down?

    Other comments have suggested that it depends on the nature of the relationship or the context of the situation. I think I agree with that.

    Do they want to know the truth? Maybe, maybe not. But I think it’s less important than whether or not you’re willing to play along.

    That’s my three cents.


  10. Ethan Bishop

    January 12, 2011 at 7:09 pm

    For the record, “what are you wearing” is not a question I would send a woman I’m not involved with on at least a semi-serious bases. In fact, I typically don’t ask that question even we are dating seriously. The only time this really makes sense to ask is if she is out with her friends at some event and she is texting me because she wants my company, and we are planning to meet after the event is over. So she is having girls night at XYZ Bar, and she starts complaining to me about how all the girls are driving her crazy and all of this drama is going on “What are you wearing” might be a way to flirtext with her until we meet later where the magic will REALLY happen…

  11. MyDatingHangovers

    January 12, 2011 at 8:07 pm

    Oh yes…the timing of this question really makes a difference and WHO it’s coming from. Random dude? Nah. I’ll reply I’m wearing thermals and crusty socks but my partner? I’ll likely get frisky as hell with my reply and then some

    Still, I’m a little tired of everything being done via text. People don’t do phone sex anymore? LOL

  12. Anonymous

    January 12, 2011 at 11:50 pm

    If a guy asks “what are you wearing” his intent is very straightforward. He wants to have phone/text/cam sex with you. How you respond dictates whether or not he’ll invest some time in trying to have that with you or whether he’ll go to Plan B.

    So, how do you respond?
    1. You think he’s hawt or you’re desperate and want to see where this goes – you lie through your teeth and tell him what you think he wants to hear (frills, etc)
    2. You think he’s hawt but want him to want you for who you are – You tell him what you’re actually wearing. If he goes to Plan B then move on; if he sticks with it, maybe he’s a keeper.
    3. You’re not into him and you want him to know it – Um, I’m wearing my boyfriend’s thighs as ear muffs so shove off already.

  13. Scarlett

    January 13, 2011 at 12:10 am

    DAMN! We having a comment party to encourage you not to leave us or do men just respond better when directly addressed?

    Men: I am single and looking. (we’ll test this theory lol)

    Yay you’re back on the Twittuh!

  14. Ken

    January 13, 2011 at 3:06 am

    Understand that everything I do, and I mean everything, is a not-so-veiled attempt to get laid.

  15. Jackie

    January 13, 2011 at 7:19 am

    If I send that text in the middle of the day when I know you’re at work it’s foreplay. I don’t expect realism, I’m trying to keep the fires going until I see next. If I that on the phone when I know you’re home it’s because I think you in your yoga pants doing laundry is sexy. I’m visualizing what would happen if I was there.

    Does that add a bit of clarity?

  16. Dean G

    January 13, 2011 at 8:13 am

    Interesting question…hmmm…its a tease mostly…completely cliche…

    I have asked a girl what she was wearing before…but never really so that I can conjure up a dirty image or to try to engage phone sex…lol

    I think it can be used as a little bit of a test of the level of interest in intimacy…also to probe the girl to see how she might respond to that question and where the conversation might lead…

    But I can for sure say that I never really would be interested in knowing what she is actually wearing…because if I like the girl I am probably more interested in personally taking off the sexy outfit or those old baggy UBC sweat pants….


  17. Shannon

    January 13, 2011 at 4:13 pm

    Awesome post.
    I never really get asked this, but when I do I’m honest.
    “What am I wearing? Jeans. I’m in the grocery store.”

  18. Anonymous

    January 13, 2011 at 7:18 pm

    Why are you and some others making this so complicated?

    As some others have said, it’s context. I’m always surprised at how so many women take men so literally. First, is it a sex thing relationship or something going somewhere or is it something? If it’s the first, it’s because the guy wants to get things hot. If it’s the second, it likely is just a way to initiate some potentially sexy banter. We don’t care what you’re wearing in a sexy way if it’s the second…we want to flirt and have fun bantering with you.

    Maybe we want to know if you’re cool…how you react on the spot? Can you roll with the punches? Are you witty? It’s about having fun and seeing where it goes.

    I talked to some of my boys about your post tonight and read it to them. They were perplexed by your words and wondered (their thoughts not mine) what is wrong with you. “Why is she taking this so seriously and literally?” was the common refrain.

    I would say why not tell the guy you’re wearing a mudmask and some really baggy sweats? Why not put the onus on him to see how he responds? He might like what you say…

    Bottomline is don’t take it so seriously.

  19. Anonymous

    January 14, 2011 at 6:24 pm

    Well. If I ask the question how are you? I mean right now. So I guess if I’m horny and I ask you what are u wearing. I mean right now. I personally get more turned on with an instant image of you at that moment. Jogging pants I think are hot. And if your cooking? Even better So I want the truth. Cos even if you look like shut I can tell you just how beautiful u really are without all the bull shit attached xx

  20. Anonymous

    April 10, 2011 at 7:20 am

    I’m not sure there’s a right or wrong answer to this one.

    At the very least, it’s a chance to flirt. Take that as you will.

    And no, there’s nothing wrong with getting imaginitive here. If a guy doesn’t appreciate that, why the hell would you waste your time sexting with him, anyway?

  21. A guy

    June 8, 2015 at 5:55 pm

    I just want to know what your wearing, there is not really any wrong answer.