Insane Things I’ve Said To Women

I don’t have a terrific grasp of how most people interact, especially when ladypeople are involved. I just say things that I think are true and/ or nice, and I hope other folks can see past my unorthodox set of references and mismatched slang enough that they don’t pepper spray me. Here are some of the most ridiculous things I have sincerely said to women both platonically and romantically in an attempt at being friendly.

“You have Catherine Keener eyes!”

I guess evidence has shown that I’m weirdly into older women who are beautiful but often exhausted looking. (I have a well-documented and longstanding crush on Julianne Moore. Also, recently I have found myself attracted to skinny but über-pregnant women as well as nannies. This all seems to point to my wanting a kid, which I don’t. Everything is very confusing. Let’s forget I said anything.)

Anyway, I think that Catherine Keener has really intense eyes, but when a woman is in her twenties, maybe she doesn’t want to hear that her face resembles that of someone twice her age. Even if that woman is beautiful and Oscar-nominated. You live and you learn. Well, maybe you do. I don’t seem to.

“I bet you were totally skinny enough to have played flute in high school!”

To be fair, I said that in response to a woman’s asserting that she was only clarinet-skinny and elegant in high school. I do not know how to comment reasonably on peoples’ weights in general, which leads me to make remarks like the flute thing as well as: “I could totally give you a piggy back for at least a quarter mile,” which is maybe more of a humblebrag about my own piggyback skills than a comment on the other person’s weight. Either way, those are two ridiculous statements to have made. How about trying, “You look great” next time. Why not just say that, me?

“Who insulted you? I’ll punch him to death! You’re perfect!”

This is something I said totally platonically, if a little drunkenly, to my friend Emily. I stand by the sentiment, but I don’t know why I thought I’d be able to punch someone to death. Maybe if that person were asleep, and I were a different guy than I am, a guy who could take a human life in cold blood with his bare hands. Even in hot blood, the worst I could probably manage would be a passive-aggressive tweet about someone. I’m glad that guy didn’t hear me and want to have a punch contest. That’s what I honestly called fighting in my brain just now, a punch contest. Still, I am happy I offered to defend Emily’s honor, even though she is capable of punch contesting her own battles.

“You’ve got real fancy hair.”

I am very conscious of other peoples’ hair, especially since I have so little of my own to work with. Pretty much any hair that is long or shiny or thick will earn a “Fancy hair!” comment from me. I’m also big into complimenting shoes. That’s in part because it’s nice when someone says a nice thing about my shoes, and in part because it’s such a non-threatening compliment to give. For some reason, I am under the impression that it puts people at ease to say something nice about their footwear. It’s not the kind of thing a mugger or creep would do.

“I want to hear every thought you’ve ever had, in order.”

This, on the other hand, is a distinctly unsettling thing to say. I’ve actually uttered those words more than once. Normally it comes after a woman tells me a story about fist fighting or knowing all the words to a Notorious B.I.G. song. What I mean is: “I think you’re a compelling person, and I’d like to hear more of your stories and opinions.” How it comes off is: “I’d like to open your skull and do experiments to that which lies within.” Or, at the very least: “I want to watch you sleep.”

Also, it’s a bit of an overstatement to say “every thought ever.” There are probably like twenty-two years of thoughts that I don’t care about at all. At the very least, eighteen years. Nobody wants to hear anything anyone thought before they were old enough to vote. That’s why teenagers have journals instead of bestselling novels. If you are a teenager with a bestselling novel, I apologize. I would like to hear some of your thoughts, in a friendly, legal way.

“Are you a vegetarian? You seem like you’d be a vegetarian.”

Ladies. Please, stop throwing your panties at your computer screens. I don’t mean to be this sexy; it just happens. Even though I’m not a vegetarian, I have a lot of admiration for their kind. To stop eating meat, you are probably either ethical or health-conscious, both of which are appealing traits. Also, it means you have mastered some measure of self-control, which is admirable. (Or you don’t like hamburgers at all, which means you are a medical oddity, and I want to study your brain for science for real.) It’s a sincere compliment that no one finds flattering.

“I like the cut of your jib.”

Because apparently I believe that women prefer to be talked to like pirates. TC mark


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  • Will

    My personal favorite:
    Girl: But I love food! Especially KFC.
    Me: Are you just telling me this because I’m black?

  • Anonymous


    • Joshgondelman

      If anything in the world can be described as “Classic Gondelman,” it is that phrase.

  • Susie

    If a guy said any of these to me I’d find it super endearing and flattering. Especially “fancy hair.” 

  • Zee

    “Who insulted you? I’ll punch him to death! You’re perfect!”
    Aww. Hahaha.

    And yes, I’d like to be told I have fancy hair too :D

  • Rich Pulvino

    “I like the cut of your jib.”

    Every woman swoons over time spent on the high seas. I say keep using this one and someday you will find your partner to pillage and plunder with.

  • Raymond Thimmes

    Catherine Keener is HOT. 

  • Jessica

    this made me laugh so hard

  • Anonymous

    As a black girl  my current favourite is:

    Boy: What’s your name?
    Me: Olli.
    Boy: Oh Ebony?


    My diction isn’t that bad I swear.

  • Paul S

    “you have beautiful skin… I WANT TO WEAR IT!!!” 

    • R

      I do this to troll my boyfriend all the time ^^

  • Sweetpea9852

    “Who insulted you? I’ll punch him to death! You’re perfect!” i love this.

  • guest

    You’ve done it again.  Another enormously entertaining article that makes me want to date you.

  • Abc123

    “You broaden my sense of purpose” – said to me, 10 minutes into date #1.

    • Louisa

      This is hilarious! Awkward…

  • Лёля

    I went to college with Josh. Wierd to stumble upon on TC

    • Joshgondelman

      Whoa! Hey!

  • Anonymous

    your articles are my favorites. 

  • Lindsay

    i’m in love with you

    • Alexandra

      Aren’t we all

  • Andrew Ricardo

    I really relate to this. Often I find myself saying things to people around me when only I know what I’m talking about. HOW ARE WE SINGE?

  • mia nguyen

    I would have giggled and bat my eye lashes with any of these comments. Well done!

  • Steven Vineis

    Older women who always look tired…they’re called “angels.” 

  • Jables

    I literally told a woman I liked the cut of her jib the other day and she just stared at me confused. Instead of rewording my statement I just restated it.
     “No really, I do. I like the cut of your jib,” I said. 

  • Shannon

    I think about 20% of guys say things like this consistently. My boyfriend, for example, once said, “I like your crazy hair.” It was when I answered the door after having let my hair air dry to its natural state (no anti-frizz curl products whatsoever).
    He honestly meant it as a compliment, but I don’t think many women would appreciate that compliment. 

  • TGold

    My dad once said to me, “It looks like you’ve been bulking up!” as a compliment.

  • internetfemale

    “i like the cut of your jib” is fucking hot. if a dude said that to me i would laugh then drop my panties

  • Guestropod

    these are all dead sexy 

  • Mackenzie

    Well, that was amazing.

  • meep meep

    bloody hilarious! oh man such a good lol 

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