It works if you’re drunk enough.
And, there’s really no downside, so why not try?
I don’t get it either. Are these men all unattractive? Are they unschooled, and know no other way of approaching a woman or indicating their desire? Neither of those seem like the reason, but I can’t put my finger on why.
On the other hand, if one is unattractive, why not make the attempt? Perhaps it’s like spamming: spammers don’t care that 99.999 percent of their attempts fail. Each attempt costs little in effort and time expended, and it’s the one attempt that succeeds that counts.
Does it only happen when you are unaccompanied by a man?
Heh. As a teenager, some friends and I would hang out just down stream from some notorious rapids and collect the inevitable beers that fell from the ice chest when they capsized. Good times, at least when you’re underage and live in a dry county…
As to the OP, I am a man, and I am appalled when other “men” do this. It’s so stupid. Heck, if you want to impress your friends with your full-on heterosexual macismo, you could just tell your friends (not the woman), “Woah, I’d hit that, then come back for seconds” or something. All the catcalls do is tell me you’re socially inept and possibly not really into women, or worse, a misogynist.
…A female sociology student rerunning that famous old experiment that demonstrates that an attractive young woman can buttonhole a complete stranger and ask him to have sex with her and get an acceptance three times out of four, while the figure for an attractive male student asking a passing woman is more like zero times out of ten thousand. 
One of my girlfriends was at a party years ago. She was down by the bar when a guy “propositioned” her with ‘hey baby, want to see me open this beer bottle with my dick?’
She squealed in delight and said ‘hold on, let me get my boyfriend, he’s GOT to see this’ and returned a minute later dragging her 6’2" boyfriend ‘this guy is going to show us he can open a beer bottle with his dick!’
I used to think all the stories I read on the SDMB were made up until what happened to me recently.
This one morning I was walking from the Metro North station to get to my dealer to score. I came to an intersection and paused, waiting for the red hand to turn into a little throbbing man. Across the street was this fox who was looking at me. I like, took off my sunglasses and leaned back, looking her up and down kind of staring at her. To be cool I didn’t lick my lips or rub my groin - she looked kind of classy. I’m sure it was sexy though even if there were a lot of people around. So I see the little man on the sign begin to throb, throb, throb. As the babe crosses the street I walk up and say, “Hey mama, when are you going to let me take you to dinner?” She looked at me, her eyes telling me how interested she was as she kept walking. Later we had sex and she had nineteen orgasms.
Perhaps you ladies would like to share a strategy that would work. I would be way too shy (or, perhaps, dignified) to make “aooga” type catcalls at a woman. I do, however, frequently encounter beautiful women in random public encounters that I would like to get to know. Is there a way to approach you on the street that wouldn’t make you recoil in horror?
FWIW, I was once crossing a street in college (Gainesville, Florida, which is full of beautiful young women), when the guy walking next to me stopped a girl coming towards us and asked, “will you go out with me?” I don’t know if it worked (I kept walking), but she did stop and talk to him.
Hilarious, don’t ask!
And yes, Sunspace, this only happens when I am unaccompanied by men. I guess they figure I am a lot less likely to try and kick their ass to defend my honor than some big burly guy who is with me, but you would think there would be some other reason than “she is alone and who knows, she might be willing to bang me.”
This literally happens every day. Doesn’t matter how I am dressed, what I am doing, what part of town I’m in, etc. And though I am indeed super sexy a Scarlett Johansen look-alike I am not, so it isn’t as if men honking at me or making verbal come ons are trying to score with Famke Jensen or whatever. I see it happen to lots of other women too. This poor woman was walking by the diner where I was waiting for a friend and she had a suitcase with her. This guy yelled out, “Oooh, yeah baby!” and ran up and tried to take her suitcase, obviously to try and impress her with his manly charms. She visibly recoiled and picked up the pace, yelling, “I’ve got it, thanks!” He stepped back, hurt by her rejection, and looked at his friend as if to say, “Why would she think someone running up and trying to take her bag would have some kind of alterior motive?” I wanted to smack the rudeness and stupidity right out of him, but as I didn’t want to get into a slap fight with some guy on the street I refrained.
But I’m really cute, and quite charming!
So, how you doin’? 
I don’t think just approaching strange women on the street or somewhere would be especially successful. A lot of women don’t like that because the implication is that you thought she was hot, and that’s why you approached her. Not that we mind being thought hot–but if it seems like or is the sole criterion–such as it would have to be for a woman you just now saw and had never met before–that can be off-putting to some.
Other than that, I have no idea.
I had a suspicion that that might be so.
There’s one episode in Sex and the City where Miranda tries exactly this approach. She’s been walking past a construction site and one worker keeps hitting on her, telling her he’s got a big one, etc. She’s between boyfriends, and one day she just turns to him and says something like: “Alright, let’s do it. I’m horny and I want to get laid! Can you do it right now?”
Construction worker looks baffled, says, “Hey lady, I’m married.”
Miranda says something like, “All talk, no dick” and keeps walking, while his buddies start ribbing him.
I’ve always assumed that bit started with one female writer coming in to work and saying, like the OP, “You wouldn’t believe what some jerk said to me on the street” and someone else saying, “What do you think he would do if you said ‘Yes’?”
What about while standing in line at the bank, or in the grocery store?
Suppose I start making small talk, offer some witty banter, make you smile (this is all hypothetical, of course; I’m too shy for witty banter); after those 2 or 3 minutes, which both of us seemed to enjoy, is there anything I can do except go on my way and wonder what it would have been like to know you?
How do you smokin’ hot women meet guys, anyway?
That would do a lot better, at least with me. However, this sort of thing happens far less with me than it does with most of the other women here. I don’t know how smoking hot women meet guys. I always assumed they just culled a likely looking prospect from the herds that gathered around them. I used to take the bus to work when I lived in Pennsylvania, and as I was (and still am) rather shy, I often read a book while waiting at the bus stop or riding the bus. Lots of comments about that, too, from “Why are you reading? Why don’t you be friendly?” to “That’s a great book, I read it recently.”
Back in the dark ages when Dr. Katz was on Comedy Central Kathy Griffin had a bit on this where she brings the construction worker home to meet her folks. “Hi, Mom and Dad I’d like you to meet my new boyfriend, Biff. He shouted lewd things to me from his construction site and I fell instantly in love with him.”
I was construction site propositioned once in college. I admit it was a bit of an ego boost. (it was finals week, I needed all the help I could get) I figured they were just trying to get a little flirt back to break up the monotony. I smiled and kept going.
If we were in line at the bank and there had been an exchange of witty banter I would be much more likely to consider it. If you come across as respectful and interesting I would certianly consider getting a cup of coffee with you to get to know you better.
Have some business cards made up with your cell phone number and keep a few handy. The next time you meet a lady who strikes your interest (and by meet, I mean you get her name and you know at least 1 thing about her…she is reading Harry Potter 7, she prefers the New York Post to the New York Times, whatever you can learn from a few moments of conversation) tell her you have enjoyed talking to her and you would love to get to know her better. Give her your card and tell her that if she would ever like to get together to call you. That way you aren’t pressuring her into giving out her personal information. I would be MUCH more likely to go out with someone who did that than someone who yelled something or other about my ass at me while I was walking to work.
Thank you so much for asking, but…no. Walking down the street, there’s very little you can do to attract my attention in a meaningful way. At least, if you have to ask, there isn’t. There was one cute charmer once who caught MY eye with a grin and silly walk followed by a nosedive into a fountain (I don’t think he meant that last part, but it was very '50’s Romantic Comedy of him). But that’s a sort of serendipity you can’t really create if it doesn’t come naturally.
If she’s a little more stationary, your chances are better. In that case, be honest and be discrete. Don’t shout at her from 15 feet away, go up to her. Say something like, “You’re going to think I’m crazy, but I noticed your eyes from all the way over there, and I’m just…overwhelmed. I would love to take you out sometime and get to know you. Here’s my number, call me if you’re as curious as I am.” And then play it by ear.
Yes, that *has *worked on me. Twice. Out of about 300 attempts (what can I say, I DO have stunning eyes! )
(Note: giving me your number is 1000X more effective than asking for mine. I’m just too nervous to give out my number. Giving me yours puts the ball in my court.)
Maybe they think you’re a parseltongue.
Sailboat
See, now this is the kind of advice us Socially Clueless Guys need to know.
::makes note to get a new batch of cards printed up ::