I’ve done #s 3&4 on your list and have done #1 but with just unattractive women. Really gets you out of your zone.

I would love to do the homeless thing. Just not in my own city where I might run into ex-classmates passing by and shaking their heads thinking “I knew he’d amount to nothing.”

Here are some that you may consider.
1. Go to an open mic poetry reading and get on stage with no poem ready. Create one on the spot and make it last for about 6-8 minutes.

2. Go jogging on a Friday or Saturday night in the hotspot of the city at around 11:30pm when everyone is partying. (I’ve done this also, people will laugh at you.)

3. How about starting a conversation with a stranger and while telling them a story, begin to cry at something that is not even remotely sad. Something like, “…and this shirt that I’m wearing is my favorite but I couldn’t get all of the wrinkles out of it this morning “sob”"

Can’t wait to see your results

And yeah, I’m known for being a bit, er…off. It’s what happens when you’ve spent the last 25 years behind a keyboard…so fair warning. This could be you. hahahaha!

Cheers! Glad you took that the way it was meant, in good fun.

This reminds me of when I was a little kid, and being driven in the backseat of someone’s car. This older teenage kid drove by and as I was giving him dirty faces he blew a kiss at me. I was infuriated by this act of mockery. Then, I would do it to other people (like the little monkey that I was) whenever I wanted to piss them off.

Long story short, winking or blowing kisses at straight members of the same sex will likely make them mad!

1) Masturbate in a room full of people watching you, pointing and laughing.
2) Go to a nightclub and dance all by yourself and wink at members of the sex you’re not attracted to
3) Visit a ranch and ask to inseminate the cows because you really want to feel the inside
4) Visit the “eat in darkness” dinner and once inside, strip to nothing (bring a towel for the consideration of those that would sit in your chair next)
5) Walk around an elementary school several times singing “Little girls” by Oingo Boingo

I’m sure I could come up with more, but you should really step up your game a bit. The five you listed are terribly easy to accomplish for most without feeling a bit uncomfortable. Different people, different things right?

Finally, if you really want to be uncomfortable, try visiting a dom and ask to be humiliated.

Have fun, can’t wait for the follow-up to this.

Cheers!

Wayne

* Join a local amateur theater group and do some acting on stage.

* Join Toastmasters.

* Do stand-up comedy or improvisational comedy.

* Karaoke.

* Stand on a sidewalk somewhere, and try to attract and hold an audience with a story you’re telling. Maybe a sign that says something like “Listen to Alex the Storyteller” would help, plus a jar to accept tips. It might be fun to try this while you’re pretending to be homeless.

OK, I’m out of ideas now. Again, good luck.

* You could forbid yourself to use any words which have more than one syllable.

* Interject lots of odd, dramatic pauses at random moments.

* Constantly speak in an excessively ornate, elaborate, literary way. Or a very old-fashioned way, or with a bizarre accent, or like a Shakespeare character.

* Bring up inappropriate quotes at inappropriate moments. “Yes, I’d like fries with that. Because, as Thomas Edison once said, ‘Genius is 1% inspiration and 99% perspiration’.”

* Videotape everything and put it on your blog.

Good luck with everything.

This idea was inspired by a zany Facebook post, in which I aksed, “Has anybody stopped. Collaborated and just listened today?”

We ended up finishing the chorus to Ice, Ice, Baby … with everyone pitching in. It was funny/brilliant. (We’re Facebook pals, so check it out.)

Anyways, when out in public, as a stranger is approaching you (preferably a cute chic), move in her path and say, “Alright stop.” When she looks at you strange and stops, start singing … “Collaborate and listen. Ice is back with a brand new invention …”

She’ll start to laugh. Then just drop her the card for your website and say, “Find out why this just happened here.” (Hand over card)

I think you can promote yourself as a psychic.. dress up in odd clothing, put up a little advertisement, get a crystal ball and give out free psychic evaluations on the street…(at the end make sure to tell them its an experiment lol)

… u can dress up in a black spandex suit and be a mime on the street. Just start performing and see what happens.

this one is kinda odd… you can ask a department store tha that has a window display if you can pretend to be one of those manican models and stand still occasionally shifting positions and see wha tpeople will think…

that’s all i got for now…

You could also research fears and phobias for some ideas. In our culture it’s creepy to eat certain bugs but you might research which ones are edible (such as cockroaches or grasshoppers) and eat a few of them. Public speaking is scary for some while laying in a coffin or on a grave, fear of heights are also fears to be faced and thus make you feel uncomfortable.

Some of your ideas, such as #4, involve deception so I can’t endorse anything like that.

Here’s some ideas:

Go to the grocery store and start taking pictures of fruit, displays, people shopping. When they tell you to stop, say “make me.” Take a print-out of the laws on taking photographs. Since the store is a public place, they cannot stop you from taking photos; their only recourse is to ban you from the store (in the U.S.). Tell them that.

Take some artistic photos, print them out through a cheap online service, and then write your name and website on the back with a Sharpie. Then start handing them out to everyone you meet. Bonus points if you write an inspirational message on the back.

Go to a realtor and say you are looking for a house in the 1-2 million dollar range. He’ll be happy to show you around, but act unimpressed at the houses you see. Eventually, find one you really like and say you’ll consider it. This works best if you don’t have 1-2 million dollars. If you have 1-2 million dollars, say you’re looking for a house in the 6-10 million dollar range.

Change your desktop background to pure black.

Go out with a girlfriend, meet people, and tell them your life story. Except make up names and stories before talking to each person, and change them every time you meet someone new. If you do this enough, you’ll have people calling you by dozens of different names.

Find an interesting blog post online, and grade it like you’re an English professor. Then post your notes and grade on your blog. Bonus points if you print the blog post, annotate it, scan it, and post it to your blog. Make sure to point out awkward clauses, improper grammar, unverified claims, straw man arguments, and other problems.

When you’re reading your next book, get out a pen and highlighter. Highlight the important stuff, write notes everywhere, cross out superfluous parts of the story. You’ll never be able to resell it, but you’ll remember that book much better than any other book you’ve read.

As for your ideas, I’d give out chocolate instead of flowers. It isn’t awkward. Don’t go to a gay club unless you want people to think you’re gay. Sitting down with strangers at Starbucks isn’t crazy.

@Dmitry: I’ve read somewhere that 4% of girls would agree. That means that, in the worst case, if you walk up to 25 girls you get 24 slaps.. and you get laid. Of course I don’t know how credible the survey was :D:D

I love the one about the bum thing.

Dress super nice and go out and try to get a really large amount of money in the form of a loan or something. And don’t goof off while doing it…really be super serious and do all you can to get it.

Go to a charity event and don’t donate any money (especially if people will notice that you didn’t donate any money).

Go up to a random girl and say, “Wanna fuck?”

1. Put on a suit and tie, except put the shirt and tie on backwards. Spend the day like that.

Here’s an idea for you: walk into a restaurant, be seated and when the waiter comes, order a glass of water. Nothing more. If that doesn’t make you uncomfortable, nothing will.

Good luck with your challenge.

1. Walk up to ~10 (or whatever number) people on the street and say “Hey, you look cool, would you like to be my friend”

It’s quite needy and out of the blue, but I promise you’ll have some great interactions. Definitely puts you on the line because of the needy angle

2. Listen to an MP3 player, walk down a busy street, and sing along out loud to the words. Again, kinda scary, but not illegal and definitely puts you on the line

3. Play the imitation game. It’s cool to have a buddy with this one, and it gets you out of your head straight away. Basically you go to a club or a mall or other busy place, and you have to tell each other what to do.

So for example I would say, pretend you’re a dinosaur giving birth while on roller skates, and you would do it. If you can’t find a friend to play along, write down some ideas from others on a list then go to a busy place and do them randomly.