The Worst Thing a Man Can Say to a Woman in Her 20's

When I was twenty, I waited tables at an Italian restaurant on the northwest side of Chicago.  It was here that I learned the basic skills one needs to thrive in the service industry: how to carry plates stacked up my arm, how to roll silverware, how to guard a walk-in cooler so my co-workers could sneak in to huff whipped cream cans.  It was here, too, that I was on the receiving end of the worst emotional barb a man can hurl at a twenty-something woman.

whipped cream can

One day, our manager, Paul, announced a contest:  He had ordered too many cases of red wine, so whoever sold the most bottles would win a free meal of their choice off the specials menu.  I was a broke college student, so the word free had an especially tantalizing ring to it.  I was also fat, so the word meal filled me even further with the competitive spirit. But winning the contest meant that I would have to come off like some kind of oenophile—describing the tannins and the flavor bouquets and such—an impossible task for a  junior at a Big Ten University.  If you couldn’t bong it, shotgun it, or smash its receptacle against your forehead, I didn’t drink it.  Needless to say, I lost the contest.

But in a strange turn of events, my friend Sarah, who also did absolutely nothing to promote the wine, happened by sheer luck to sell the most of it.   She was (and is) a great friend of mine, so after her shift, she agreed to share her spoils of victory with me: a solid pound of pesto gnocchi with shaved parmesan. “I did it all for the gnocchi!” she sang, riffing off a Limp Bizkit song that was popular at the time.

We blithely dug into our mountain of potato dumplings and began to discuss our favorite conversation topics: parties and boys.  One of our co-workers, a Bible-beating, weight-lifting YMCA resident named Obide sat watching us.  Over the course of the summer, Obide, who was a teetotaller, had made no secret of his disapproval of our debaucherous ways. This time, he sat listening to us for awhile before finally shaking his head sadly and whistling in a low, mournful tone.  Obide was a great whistler, because his teeth were so crooked he could eat a head of lettuce through a tennis racket.

“If y’all keep carrying on like thith,” he said sadly.  “ ain’t nobody gonna wanna marry you!”

And there it was: the most hurtful thing a man can say to a young, single woman. At the time, I wasn’t even thinking about marriage.  I was embroiled in a pathetic summer fling that would end, in flames, that September.  But it didn’t matter.  It still stung—badly. Even if you don’t ever want to get married, you certainly don’t want to be unmarriageable.  If you want to remain a bachelorette, you’d like to do so on your own terms. To be marriageable means to be respectable, to have class.  When someone deems you unmarriageable, they are essentially saying that when they look at you, they see a person whose genetic makeup is best left weeded out of the succeeding generations of humanity.

I wondered: what had I said over the course of my employment that would make Obide think that no man would ever want to marry me?  Was it the fact that I often showed up to work unshowered and hungover after a late night drinking in the forest preserve?  Was it the fact that he had overheard me agreeing to go to Howl at the Moon with Greg, the perverted  food runner?  Was it the fact that, on one occasion, I, too, may have huffed a whipped cream can?

After his comment, Sarah  and I looked at each other, laughed it off.  We ate our gnocchi. But it tasted gluey and depressing.  And after we both quit, we never spoke of Obide—or his insult—ever again.

So how do I know this is the worst insult a man can say? Because in ten years’ time, neither Sarah nor I ever forgot it.  It turns out that I did find someone to marry me—someone wonderful, even, who I love like crazy. We got married on August 17, 2012, exactly 5 years to the day since Sarah also found someone to marry her.  And when she walked into our wedding reception, she didn’t congratulate me or my husband.  She didn’t compliment my dress or my hair or my ring.   Instead, she hugged me and whispered in my ear:  “If only Obide could see us now!”


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  • Another great column, J-Mo. Thank you for your honest perspective. People who watch the show "Girls" might have assumed that the worst thing a man can say to a woman in her 20's is : "We should move in together." or "I really love you."

  • Yeah, the guy was insulting.

    Want to know one of the worst things a young woman can say to a man she is or have had or is in the process of deciding whether to go further with him; it's this: "You are nobody I think I can build a life around".

    A guy would rather hear he has body oder, is stupid, is addicted to something or has bad breath, but when you are young and vulnerable, it stays with you for life, too. She said, after chasing me down, that I was, in effect, "nobody", not for her and not for anybody else. That proved false, but it stung. So, tell you single friends to tell a guy they decide they do not want that he is flawed, but not to the core.

    This happened to yours truly, by somebody who pursued me after we had drifted apart as you often do when younger; there was nothing that broke us up but being busy and living a good distance from each other.

    Words do have consequences, but years from now, when you are long into your relationship, be wary of those words coming back to you and playing tricks with you mind and position at the time. Maintain the positive picture you have of yourself, because your core is the same then as now as it will be thirty years from now.

    One could even say that the words still resonate with you, because of this blog. Better to live in the present and be aware of the context (false) in which you were insulted.

    All is well that ends well -- if you make it so.

  • In reply to Richard Davis:

    Brutal. And whereas Obide (who is now a character I'll never forget) was attempting to give some misguided, loopy, and insulting advice, the young woman who said that to you was specifically trying to de-value you. Men, as the popular culture constantly reminds us, are guilty of all kinds of offenses against the women they date, but the types of deliberate hurt many women inflict on men are largely ignored, in my opinion. This is the result of the odd bedfellows of pseudo-feminist entitlement and misguided chivalry. Somewhere along the line "female empowerment" got twisted in the minds of many to mean the the feelings of men don't matter. Circumstances weren't ideal for your relationship, so it didn't work out. But she had to assert that your total lack of worth was the reason. Her fragile ego was the only thing that mattered, and you were expected to just "man up" and deal with it. Thanks for calling a spade a spade. I think Jessie's column is going to generate a lot of really honest, interesting discussions.

  • In reply to DGDG:

    Yes, true about asserting my total lack of worth, but it hit harder than any blow could have at the time. Maybe due to my lack of self-worth at the time. However, thing said like that at certain times can have the tendency to be buried in your unconscious and resurface years later when a similar circumstance or words occur, whether said in anger or in defense of ego. That is why I hope that Jessie Anne can recall the proper response years from now when life and living and setbacks (which I hope do not occur) can flood the body and mind and emotions with the wrong thought, that the new Obdie is the same as the old Obdie, and to frame it in proper perspective. Sometimes, even though we know better, we get caught off guard.

  • upto I saw the check which had said $9509, I accept neighbours mother trully making money in there spare time on their apple laptop.. there friends cousin has done this for less than 18 months and as of now repayed the loans on there condo and bought a great BMW. go to, >>>>>><<<<<<

  • In reply to jakiechagnon67:

    No way. Really? That's off the hook!

  • In reply to jakiechagnon67:

    That s*** was da bomb.

  • Loving this blog already-funny, smart, with just a splash of self-deprication. I totally agree DGDG. I think our culture is too quick to overlook men's feelings in the battle of the sex's.

  • Thanks for your responses, everybody. In future posts, I am definitely going to be exploring the [false] idea that women "feel" more than men do--and that therefore, we need to be more careful of women's feelings. Anyone who's truly loved a man--or truly hurt one-- knows that they experience the same kinds and intensities of feelings we do.

  • Jessie Ann, I was with you until you wrote this.

    “If y’all keep carrying on like thith,”

    Very general rule: belittling someone because of something they can't change (or can't afford to fix) crosses the line from being amused by someone's idiosyncrasies to saying something ugly about yourself. If his teeth were bad enough so that he had a speech impediment, making fun of it even 10 years later is in really poor taste.

    To me, that comment was more or less identical on a moral level to the insult this guy hurled at you; the only difference is that you're now 10 years older and at 30 you should presumably have grown up enough so that your behavior doesn't get as much of a free pass as you did back then.

    Might want to think about that a bit before you keep blogging.

    Good luck.

  • In reply to Craig L:

    Craig, basically you're against the basis of all humor. The nice thing about the situation, though, is that you're free to not read this column if it's too painful of an experience for you.

  • In reply to DGDG:

    And usually, when someone pulls the "humor" card when someone is offended, it's because they can't appropriately defend what was said.

    Try again. Good luck.

  • In reply to Craig L:

    Sorry that I pulled the "logic" card on you, Craig. Did that offend you, too? Much as you would like to run the world, you don't, and the burden is not on me to defend what I find humorous. It goes without saying, but I'll say it anyway--if every line that offended someone was pulled from humor columns, we'd be left with some pretty dry reading material. I suspect that you are highly selected when it comes to throwing out the term "offensive" and that the things that strike you as funny are often at the expense of groups and individuals that you think "deserve" it.

    Whatever the case, your ultimate goal is to censor. That's sad. But please, by all means, keep on clicking on this column.

  • In reply to DGDG:

    "highly selective"

  • In reply to DGDG:

    How funny. I wasn't the one who told someone to stop reading the board, which generally is regarded as censorship.

    And even funnier - if you want to start addressing the meat of my comments rather than keep doing ad hominem attacks, feel free. Otherwise, the only ultimate goal for you seems to be a troll, but hey, that's the intelligence level of the internet nowadays.

    But please, by all means keep posting. I enjoy humor, even when it's unintentional.

  • In reply to Craig L:

    You've already established that you have no sense of humor, so you calling anything "funny" is terribly lame.

    But, anyway--good boy. You're very obedient. As you know, I said you were free to simply stop reading this column if you were too delicate to handle it, but it's wonderful that you keep coming back. Keep lobbing me these softballs. There is no "meat" to your comments. You're just a cliche of a self-appointed P.C. policeman. What a terribly sad existence you must lead.

    If one great line from a ChicagoNow column inspired you to write a lengthy condemnation, the broader world must be too much to bear for you. You burst into tears during every episode of SNL, because it's just sooooo offensive, don't you? Lorne Michaels gets a LOT of strongly worded letters from you, right?

    You really enjoy the punishment, don't you? Typical troll.

  • In reply to DGDG:


    More ad hominem flames. How boring. Might even be fun if you started in defending how exactly belittling a speech impediment when you're claiming massive victim status is two-faced. Oh wait. You're too busy making things up.

    You go girl/guy. Can't be bothered to do much more than to throw mud. Definition of a troll, but self-awareness doesn't seem to be one of your characteristics.

    And by the way, she's no Mike Royko. He could be brutal, but he was also funny and stuck up for the little guy. What's your relationship to her, an internet BFF or something more offline?

    Continue making a fool of yourself if you'd like.

  • In reply to Craig L:

    THTOP it, Mr. Craig! You betht stop methin' with jethie, thucka! I am for therious! I never athked you to thick up for me, fool! Now go back to yo Readerth Digest boolthit and leave these nithe people alone.

  • In reply to Craig L:

    Your attempt to throw a low blow here falls flat because you've either never read Mike Royko, or you're deliberately misrepresenting him and his work. Like him or not, Royko was an equal opportunity offender. The line here that got your panties in a bunch was simply dialogue written as it sounded. Royko engaged in deliberate caricature and out-and-out insult humor, and he did not reserve his wrath only for the plutocracy, as anyone who read him would know. If you actually did familiarize yourself with his work, you'd become apoplectic. Then again, reading a Bazooka Joe comic would probably make you stomp your dainty little foot just as hard.

  • Craig, basically you're against the basis of all humor. Happily, you don't have to read this column if you find it too painful.

    Good luck.

  • The funny thing, CRAIG, if that is your real name, is that at no point in Jessie's article did she make fun of him. She merely wrote, in "eye" dialect, how he sounded.

    You see, Craig, when one writes something, they try to their best ability to portray a characters voice in a unique way so that it doesn't sound like the other characters voice. Thus, Jessie used a technique in her dialogue to that you would be able to see and hear what Odibe sounded like.

    It was you, placing your own biases, your own sensitivities on to what Odibe had going on. I know a lot of people who have speech impediments, and I consider them my best and most trusted friends. I would go to war with those marble mouthed beauties, and they with me. Yet, when they read the article, never once did they seem ashamed or offended.

    I would encourage you to read on, because I feel like this can be a great learning experience for you. I think one day you might even be able to move out of your mothers basement.

  • In reply to zydowsky:

    I always love the 'friends' claim. Pray tell when they read this article, or are they in mom's basement with you and your PS2?

    And the only learning experience is that when people are rude to others over a long period of time, it's no surprise that they'll fight back.

  • In reply to Craig L:

    Now you're jutht projecting, Mr. Craig.

  • Oh man. This shit is getting real

  • Craig, I'm sorry you didn't like my post. But nobody's making you read it, and nobody's making you come back to comment on it with your own brand of ad hominem attacks about me and my "internet BFF's" (speaking of poor taste).

  • In reply to Jessie Ann:

    And nobody is making you write these posts either. Welcome to the real world of blogging - anyone can read, anyone can comment, and if you don't like it, you don't have to keep doing it.

    As an educational point, haven't made a single ad hominem attack 'about you'. The critique of your writing is more than sufficient; it's certainly no personal attack to point out your claim of victimization falls a bit short when you do the exact same thing to someone else.

    And by the way, did you and your friend feud with this guy all summer? Makes a lot more sense for him trying to burn you in the way that he did, and makes a lot more sense for you burning him now. Kinda sad after 10 years, but whatever.

  • In reply to Craig L:

    We were on exthellent termths, Mr. Craig. I'm thorry I hurt your feelings, Jethie. I really am.

  • Well, Craig, I do hope you at least keep reading my blog. I have many more offensive things to add to the conversation.

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