You should do this anyway - it is a huge confidence booster (if it works of course).

Pick a cute girl - she has to be on her own, preferrably standing (if you are "above" her when you do this it's a bit overbearing). As soon as you spot her (leaving it 10 mins will just look creepy :)) walk up to her and say "hi, hows it going" (her: "hi, err fine"), "what are you doing later?" (her, probably: "not much"), "Do you want to come home with me?".

Say it seriously (but not creepy serious) and lightly (dont laugh or smirk) as if you were asking about the weather. And then just wait (if she says "what?" just smile, it's crucial not to add anything else). Chances are she will say no (getting a slap is very unlikely). Whatever she says just carry on the conversation as if nothing ever happened ("cool, im justin. who are you?" offer hand to shake, "sweet - when did you get here?" etc etc.). She might just walk off. If that happens just ignore her - chances are she will come back.

To "win" the challenge you have to buy her a drink (if you got up the balls to ask her this wont be even an issue).(warning buying the drink will more than likely put her off a bit).

(and, yes, I've done this - it's great if your feeling like a confidence boost! It works as a boost because there is no way they can say yes - so even a no is a result. Just asking the question is worth a million :))

@darkxanthos convince a stranger to go skydiving with you (the plane kind) or perhaps convince a stranger to start their own social skydive

I wanted to give you my ideas for the Social Skydiving challenge without the hassle of signing up for the comment systems. So, I hope you see this here.

I have a lot of ideas, most of which are probably junk. But, your blog struck a chord in me, so I've written them out. I've not proofread much, so hopefully most of it makes sense.

PROLOGUE:

I think the most stressfully embarrassing social situation I've ever faced was one time at a Renaissance Faire. If you're not privy, a Ren Faire basically consists of hordes of hippies pretending they're from the 15th century with questionable accuracy. For patrons, it's a campy carnival of perverts with pathetic cockney accents. For workers, drunken weekend parties ensue betwixt the adults (armed with the usual hippie supplies, if you know what I mean (drugs!!)) while the children are left to wallow weekend after shower-less weekend. Your imagination probably does a pretty good job of filling in the holes.

As such a child of some Ren Faire workers, I spent my weekends of each Faire Season dressing like a serf, playing with wooden weapons, watching the stage shows again & again, and occasionally pausing to help run my family's booth (a historically inaccurate but fun game).

At some point in the season, we attended a seminar about hawking our booths to the passerby, taught by a long-time Fair veteran. He was of a kind; I don't expect just saying "suave Ren Faire guy" suffices, so I'll try to expound. He was one of those charming guys, not old enough for it to be creepy and not young enough for it to be cliché. A magician, which in Ren Faire terms translated as "cool", for whatever reason. Clean-looking, talented, and effortlessly proceeded with the charmingly light-aired social interaction of the Faire. It's kind of weird to explain. It's as though Ren Faire gave guys carte blanche to be womanizers.

But he made his lessons in attracting people towards you seem effortless. Of particular note was his observation that people came to the Ren Faire to be immersed in the campy sort of atmosphere. That a powerful selling device was merely sexual appeal: the women certainly knew it, since they wore bodices that prominently created cleavage no one knew they had, and the guys knew it because so many got away with being perverts. Chicks worked the ale stand, goading drunken men into tips, and guys invited 14-year-old girls in small white summertime shirts to the water-dunking game. So, an underlying tool of the seminar was that you could "woo the women". That was the exact phrase; it stuck in my head.

He demonstrated how coolly he could proceed to flatter a woman, gently offering his hand, with a bow, to the accepting lady. She passes her hand into his that he may raise it to his lips and deliver a simple kiss. He locks his eyes on hers, giving a gentle squeeze to the hand, tempting a reciprocal squeeze. "Oh, you have a nice grip, m'lady. Surely you could [throw a dart | ring the bell | something vaguely related to the booth he was advertising]."

Just like that, he had his customer, and they both had fun being a part of the situation. It struck a chord in me somehow: that's easy! And so, the first of the embarrassments start as I confidently assert -- aloud to my family -- how I can apply the lesson in helping get customers. When I get my clothes wet and look frumpy, I start lamenting how I won't be able to "woo the women". etc.

Predictably, I sat on my laurels, watching female after female pass our game while I did nothing. My dad asks if I'm ever going to do it. I assure him that I will -- that I just hadn't worked up the gall yet. He tells me to just go out there. Still, I wait.

Sick of waiting. Swallow my fear. First group of appropriately-aged women pass by, and I pounce. In a slur of awkward grabbing-at-the-words, I realize how I should have thought of something to fucking say. From what I remember, it went something like:

"Aye, but for the...you are surely the l-loveliest lady to, uh, grace our...beloved Faire."

As if it was not enough that I had just jumped out in front of these moving people, causing them to halt abruptly, I was now fumbling over some half-assed attempt at flattery.

Not just flattery. I was kneeling before her, my head bowed and my hand outreached in the traditional gesture. ...And she wouldn't reciprocate. Not out of disgust or anything (I'm fairly sure), but out of sheer confusion. The utter bozo that I am, I take it upon myself to grab her hand from her side -- with a little too much resistance for it to be comfortable -- and plant an awkward kiss upon it. I remember how hot my face and chest ran from the pangs of humiliation that shot throughout the empty cavity that was my body (for you see, it was empty after my stomach plummeted straight out of existence).

Still, I battle through it. Confidently look forward, lock eyes, and squeeze whatever I was holding -- only to find her limp, lifeless hand not responding.

To describe the momentary silence as an "awkward pause" fails to do it justice. I was looking up at her, and to this day, whenever I picture it I can only remember seeing her looking like Lydia from the movie Beetlejuice. And I have no idea why I remember her looking like that. I'm almost 100% certain she must have looked drastically different from that black-garbed character. But that's the image that lodges in my mind for some reason. The sheer awkwardness is only punctuated by (what I assume to be) the girl's mother:

"What do you say, dear?"

"Um...thank you?", she forces.

And the 3-person group (or at least I remember it being that large) continues walking away. As her hand slips out of mine, all I'm left with is an aghast fumbling for more words. Everything about the "wooing" had failed; hard.

"Uh, um, w-would you like to play our game?!", my stupefied voice calls all-too-loudly to their backs in a perplexingly transparent fashion.

The mother turns her head back. "Oh? No, not today, sorry."

The arm I had just done the deed with falls lifeless by my side. I'm left with nothing but my hideous resentment, humiliation, and shame. I quickly about-face back to my dad, collapsing in his lap, where I cry. A lot. It must have taken me hours to calm down (I don't actually know how long). To be fair, I must've been about 10 or 11 years old at the time...

Wow, that was painful to write about. And not even because the vast amount of failure made a fuck's bit of difference in my life (though I've never since tried a stunt like that!); if ever there was a time to get away with it, being a little kid certainly helped.

So, this isn't an idea for your challenge; it's a guideline: if you can face something as embarrassing to you now as this was to my 11-year-old self, yet walk away learning something, I'd call it a success. If taken in objective terms, you've probably faced situations in this 30-day adventure that sum to more total embarrassment than my 1 fleeting pre-adolescent encounter. Taken in all its context, however, it was probably the most embarrassing thing I've ever done.

IDEAS:

Note that these are mostly social experiments I've always wanted to try but never got myself to do (excuses!). They're a bit far-fetched, because they're designed with an eye towards just seeing what results you get, rather than engaging in conversation or bettering yourself socially.

Games:

A theme you address is the restoration of child-like wonder. One thing I think we all lose as we grow up is our sense of simple, spontaneous pleasures. Things you can engage total strangers in. The problem here being that if you fail to get the event rolling, it all works out boringly -- you've hardly failed at all if you fail to do this, but if you succeed, you have an awesome time. So, I don't think these are very good challenges. But, I've entertained these thoughts.

In her routine The Beginning, Ellen DeGeneres suggests that you "just go up to a total stranger tomorrow on the street, just go up to him and just touch and go 'YOU'RE IT!' and just run away. Have a giant game of tag going on on the street all the time."

Similar ideas that are more prone to Big Failure involve dialog, because at least you have to say something aloud. Maybe you could get a bunch of strangers to join you in singing some classic song. Something everyone's comfortable singing -- something they'd know at least some of the words to. I've done this with songs from The Lion King, for instance. Maybe a dramatic scene from a well-known movie people would know the dialog to. These might be easier with some seed set of people instead of just you, though; at least n > 1 could finish out the song or scene in a way that's less likely to get you kicked off the bus.

Persuasion:

Other people have had ideas along these lines, and I think it makes for a great class of challenges: convincing strangers to do something with you. It not only helps build a common ground a bit more solid than smalltalk, but if you fail you get to have people think you're some sort of weirdo!

Elevator patrons make for an interesting random sample of people. They're usually looking to get away to somewhere, so most of them won't give you the time of day. I've long pondered experiments you could carry out in elevators, though:

- I once rode an elevator in a college dorm where 3 or 4 residents were sitting on the floor playing cards. This is probably easier to get away with in a dorm, because you aren't strictly going to interrupt business with a weird/cramped elevator trip -- versus, say, your workplace. These kids were doing it just to be weird, but you could use it to invite strangers to play cards with you. See how big a group you could get going. Engage in conversations over some cards. If they decline, they just have a story about some weirdo in an elevator playing solitaire. Now, if you're in an elevator that serves to traffic people with business purposes -- somewhere to go on a schedule -- you probably won't get many people to come along with you, due to the sudden nature of engaging in a card game. You could tweak this to a different, more conducive environment: in the halls outside of a classroom? In the classroom before the lecture starts?

- An experiment I thought of with goals similar to Social Skydiving was to hang out in an elevator. People are surprised when there's someone in the elevator already, just riding. It is kind of weird, after all. It's sparked conversations for me before. My idea was then: if I saw any attractive women, bluntly ask them if they'd be interested in dating me (phrased with various layers of "hypothetically, of course!", if need be). The aim was not to actually get any dates, but to convince myself that it was easy to ask and that it'd get more comfortable with time. (Of course, I've always made excuses, so I've never actually done this.) If anyone gets too weirded out, you can use the excuse that you're performing a random survey. Then, even after social side-effects (self-improvement, yadda), you would have some interesting data. See what range of reactions you get! While it probably wouldn't make you seem any less of a geek, it might deflect animosity.

Okay, enough about my weird fascination with elevators...

- Growing more overtly sexual, you could pull off a stunt like in A Complete History of My Sexual Failures (http://www.imdb.com/title/tt1037033/), a documentary wherein the maker barges outside and proceeds to parade around the streets, begging various women to have sex with him. He was threatened, some ran away from him, hilarity ensued, but not only did it take awhile for the cops to interject, (SPOILER ALERT!) he got one positive response. I don't know how much the camera following him helped the entire situation. With "oh, I'm doing a documentary and I'm drunk and took way too much Viagra", it's easy to write someone off as a harmless lunatic.

- More harmless (still creepy), you could give a pretense to go out and do something with someone. "I have some tickets to [Disneyland Seattle | Six Flags | minigolf | whatever it is you guys have], but no one to go with. You in?" Such abruptness would probably make people distrustful. I know I wouldn't agree to go somewhere with a random stranger; he'd probably just try to kill me in the parking lot. So, you can lead into it. Strike up a conversation, and if it's going particularly well, try to edge in something to convince them to go with you. Probably shouldn't press the issue if they decline, of course. If the outing is sufficiently innocent, you shouldn't come off like you're trying to get into their pants.

- Ask people what you should do for your challenge. Strike up a conversation and work towards divulging that you've been doing the Social Skydiving experiment (Smile! You're on Candid Camera!). If they're interested, discuss the results, the finer points of social awkwardness, and ultimately ask them what you should do as your Mega Capstone. Ask them how they could be involved in carrying out a plan. Maybe that could blend well with the other ideas -- "I was thinking of going to [do something] with someone I just met".

This, of course, presumes an ideal conversation. If you've learned anything from this, you'd be at least a little bit equipped to steer the conversation into the area you want it. And it probably helps having this clear-cut goal of the conversation. In disclosing information about yourself, it's much less phatic than standard smalltalk and has potentially more lasting effects.

- In some cases of certain social anxiety, doctors will have patients publicly declare something. e.g., Have someone who's embarrassed to admit they have a stutter announce it to a bus full of people. This isn't a specific challenge, but something worth considering: something very public where you disclose some personal info. Not unlike your blog, but doing it face-to-face instead of written-down can be intimidating, hence proving your increased bravery. Something as short as "I'm Justin, and I stutter" isn't going to be worth it as a challenge, but I wouldn't know what else you could announce to a large group of people. Maybe you could see if they'd listen to you talk about your Social Skydiving experiment?

- In an effort to heighten the level of discourse with strangers, instead of discussing the weather you could debate them. Of course, debate about certain issues becomes just as phatic: "I LOVE BLAH!" "BUT I DON'T!".

At my school, every so often there'd be these guys with giant banners listing Satan's Children, including groups such as "Mouthy Women". This would often encourage little islands of conversation. I mean, sure it's part of his business plan (seek out high-traffic areas, piss people off, then magically they're talking about religion instead of just ignoring him), but the conversations are so much fun. My friend and I went down to yell at these dudes once. I got to creep out the Campus Crusade for Christ kids by asserting that I wasn't actually there to argue that Mouthy-Women-man should spread the Word of God in a nicer way. Stuff like that. Play the Devil's Advocate. Automatic conversation & debate starter. And more interesting than the weather!

It's harder to debate someone spontaneously, though, without resorting to the same tactics (which wouldn't necessarily be a bad challenge...).

- If you're like me, you have some old friends that you don't talk to anymore. Sure, you guys used to know each other & talk during high school or whenever, but it's been 5 or 10 years, and it all just kind of...died off instead of being any deliberate sever. If you're even more like me, you have social anxiety about even starting conversations with those old friends (who you can easily track down). "What if the conversation doesn't go right? That was a long time ago that we did such & such. We won't have anything to talk about, because we don't have any context for each others' lives." etc. If you could reconnect, it'd be interesting, but thinking about them is like remembering a ghost.

But, instead of paralyzing yourself with these fears, try it out. See what they're up to. Reminisce. If you can carry a conversation, you succeed. Try it with something like the phone or face-to-face, if possible, so that you can't hide behind switching your IM client to "Away". It has chances of being more meaningful than talking to strangers, even though you might discover that they are strangers after so long.

You could be even crazier and contact the people you had a bad time with, like the maker of A Complete History of My Sexual Failures contacting all of his ex-girlfriends.

If you don't have any old friends / acquaintances you'd want to talk to like this, then the idea's a bit of a lost cause. But I think it'd be cool if you did.

I've enjoyed following your blog. Best of luck!

Having said that, I really wish that since you took the time to write all of that down that you would have taken the time to register to comment.

A lot of people would see that and it would help a lot of people like us out.

Anyway, thanks soo much again. Hearing your ideas and your story is going to be one of the experiences I take away from this experiment.

Didn't think of it that way. If you think the post would help people, I could cross-post. Or you could post a link and/or copy & paste the text, if you'd like.

If I'm handing out free money why not hold out your hand? :)