Way back when, my buddy and I were goofing off at the pool one summer with a couple of female friends. In an attempt to toss her into the water, he grabbed one of our friends, who shrieked:
“Put me down. I’m too heavy.”
He had worked most of the summer at a plant nursery, and replied:
“Nah. I’ve lifted trees that were heavier than you.”
And then dropped her into the pool.
I once had another woman say to me, while lined up and about to take the floor for a dance competition, “I love the expression on your face when you dance. You look just like my golden retriever when he hangs his head out of the car window.”
Background info: Until my junior year of college or so, I still had a moderate case of acne. It wasn’t horribly bad, but I did have a problem with zits and the like. None of my friends ever mentioned it or anything, because, well, that would have been totally rude, and besides, it wasn’t THAT bad.
So there’s this guy I’m dating/sleeping with, my sophomore year. He comes over to my dorm room one evening, hijinks ensue, and as we’re lying there snuggled up to each other, basking in the afterglow, he says:
“Hey, do you think there’s anything you can do about your acne?”
The punchline is that my self-esteem was so poor back then that it took me four more months to dump this loser.
I’m three months pregnant with our first child, puking my guts out three or more times a day. My husband follows me into the bathroom to witness the revival of my breakfast and says,“Damn, Baby, I could drink a whole case of beer and not be as sick as you.”
Big Daddy D, Yikes!!!
The worst thing a guy can do is tell me about his ex-girlfriends’ sexual habits.
Not mine, but got said to a close female friend of mine just last week. She was on a date with a guy she’s gone out with a few times. She was joking around, making some insecure comment or another about her weight–she’s not fat at all (actually, she’s just about the ideal weight for her size, IMO), she’s just not unhealthily skinny–and he says:
“Well, all the other girls I’ve dated have been skinnier than you . . .”
Oddly, she didn’t come home with his testicles mounted as an antenna-topper on his car. Can’t figger it out, myself.
Can’t think of anything of my own. Women don’t usually talk to me long enough for me to say something really stupid. 
Hey, maybe that explains the silence! On the other hand, no, I don’t think that it does…
i’m not sure if I have shared this one here regarding Mr. Ujest, but it is a corker.
A woman at my husband’s office received a fur coat for Christmas. Everyone was standing around admiring it.
Up walks my husband who pets the proffered coat covered arm and says, " This is nice, what is it, possum?"
The woman says with a straight face, " No, it’s beaver."
Mr. Ujest continues to pet the fur, " Barb, I like your beaver."
(And he did not mean it as a joke either, but everyone else nearly pissed their pants.)
As my own ex will attest, there is often something of a disconnect between my brain and my mouth. Usually it ends pretty badly and is not at all humorous. This one’s not so bad, though.
We were talking on the phone a few weeks before her birthday for some reason. I forget the exact context, but I said, “yeah, this will all be so much easier when you turn 18 next month.”
She was 21.
I neglected to mention that we had been together since she was 17.
Two bad ones: Once I had a girlfriend I constanly (unbeknownest to me) would Freudiantly call by the name of my ex (and most significant other to date). Another one: Last summer I officially met a woman for the 1st time (worked near her for 6 months). I saw her nametag, and asked,“Guess your parents really wanted a boy?” She wasn’t mad at that, but we evtually had a falling out.
It’s funny, dating women I don’t find they take things the wrong way as much as my straight friends seem to with their boyfriends. I’ve had the ‘who else do you find attractive’ discussion with no problem. Perhaps that is because as a woman I didn’t answer with a list of every female under 50 within a ten-mile radius.
A bloke I know overcompensated on the pregnancy issue. He runs the local corner shop, and I used to know him fairly well, and I saw him in there a few times when I was 9 months pregnant. After my child was born, I was in there again:
Him: I didn’t know you had a baby!
Me: Um, mine.
Him: Oh, I didn’t even know you were pregnant! I thought you just got fat!
Now, I’m pretty skinny and and there was no way you could think this protruding stomach was ordinary fat. Nevertheless, when I got home I still felt compelled to examine myself to see if I did look fat after all.
This one’s my husband’s comment. We were driving along in a car, and pass a female jogger in a sports bra and very short, silky running shorts.
Him: Mmm, look at that, nice ass…
Me: [realization that he didn’t mean to say it aloud, and clamp hand over mouth as I laugh]
Him: [unaware of what’s just happened] What?
Me: [laughing even harder that he doesn’t realize he said it aloud]
Him: What?
I actually had to, once I stopped laughing, repeat the sentence back to him before he realized he’d spoken his thoughts. I laughed harder after that, but wasn’t mad at him, because he was sincerely embarrassed.
ME: [Festus voice] “Honey, yew look purtier than a $20 whore” [Festus voice]
Her: SLAP! “WTF thats suposed to mean?”
She’s obiviously never seen Gunsmoke.
I have this one group of friends that is very raunchy. We will constantly rip each other on anything, (And I mean everything, nothing is off limits), nothing is let go. It’s all good fun, and everyone has a blast. However one time after a three day camping trip, my brain never switched back into polite society gear.
Just after, I was over at another friends house, and met his girlfriend for the first time. She was cute, and just the slightest bit heavy(important to the story). She was making us dinner. She leaned over and started looking into the fridge and said ‘I thought I had some cheese here’. Her ass was up in the air and I found myself instinctivly saying;
“Well, From this point of view it looks like you’ve at least got plenty of cottage cheese”
oops, wrong person, wrong situation.
I faked a call from work, and wasn’t invited over again until they broke up.
Here’s one from one of my guy friends- I took him into a leather/fetish shop, mostly to see his reaction, but also partly to visit the coat I want… well, he nearly fainted, and complained for the next eight blocks. When I asked him what bothered him about the store, he said he objected to its turning women into sex objects. Fine. [iThen* he said,
“Women aren’t only useful as sex objects. They can do other things, too, such as cook.”
I beat him mercilessly with my umbrella. He still pretends that he thinks he was being very liberal: after all, he DID say we’re more than just sex objects.
I once had this conversation with a guy, whom I had rather a large crush on, after a night spent by him and the other male members of our school group in an “exotic bar” somewhere in Rome, Italy.
Him: You would’ve liked it at the strip bar last night, you should’ve come.
Me: nodding politely, thinking, “ok…?”
Him: One of the strippers reminded us of you.
Me: WTF?
Him: We nicknamed her the Wild Beast, because she was so ferocious.
Me: Super-WTF?
To this day I can’t tell if I should’ve been insulted or oddly flattered or if it was meant as an entirely neutral comment. I should note that this guy, upon discovering that I would join in on commenting on attractive women we saw pass, had decided I was a lesbian, and could not be dissuaded from this belief.
I can’t really recall any bad thing I have said to a woman.
Well, that’s because I usually get smacked upside the head and those instances have been jolted from my wee male brain.
Nearly all of my friends are male, and, though a female myself, I am (compared to other girls) quite masculine in appearance and behavior, a fact which generally leads to much ripping-on if I acknowledge my own femininity.
Me: “Am I a slut?”
Friend 1: (pause) “Nah, you’re too ugly to be a slut.”
Me: (discussing a neighborhood which one friend has described as being dangerous) “Dude, I’ve walked around there after midnight a buncha times, and nothing bad’s ever happened to me.”
Friend 1 and Friend 2, in almost perfect unison: “Guys don’t rape ugly.” They both put their hands to their mouths immediately after saying this, and I was laughing too hard to be mad.