Still, total cake. Go to a bar that has a drink menu, start at the top and go in order.

If you are in Vegas, and doing other things while trying to win this bet, and not having the whole trip revolve around this bet, it would become kind of difficult to order a different drink everytime. You are at Casino Royale playing craps and you just had a coors lite, and the waitress comes around asking for drinks, and you are already 12 deep on the evening, and you are shooting and quickly ask for another coors lite....gg bet

Obviously the first 5-7 drinks are cake, it is after you are drunk that makes this bet difficult, and if you are a low roller playing at low end casinos with a very small beer selection.

At a minimum, I think I am going to try and not have the same drink twice on my trip at the end of the month.

As stack510 said earlier, there is more to life than a jack and coke. A change from the 42,000 coronas would do me well.

Maybe you could just tell the waitress to bring you something new each time. That could be interesting.

If you didn't allow me a cheat-sheet and just sat me down at a bar right now and said I couldn't repeat the same beverage for 4 days I would bet my entire net-worth and whatever I can get other people to stake me [perhaps up to $1 million] to win your $100.

That's how sure I am that this is incredibly ******ed. But you don't seem to be April Fools'ing on this one and I assume that you are actually serious.

If you made it for an entire month of not being able to repeat the same drink then I believe you START to get into the 'somewhat difficult but not impossible category' and I still think I would be able to do this.

If I had to drink 4 beers a day or something and then go the 31 days trying to come up with a different beer every day then that would be a challenge I guess but for me it's partly because I don't know much about beer.

do dewars and johnny walker count as two different drinks?

two different scotch whiskeys

does dewars and jack daniels count as two different drinks?

a scotch whiskey and a tennesse whiskey

How do you seperate kinds of beer?
By lager, pilsner, etc.?
By Bud, Coors, etc? or By Sam Adams Summer, Sam Adams Lager?

Even with just "beer" and "wine" being single catagories you can get tons in. The first 20 that come to mind...

Beer, Wine, Rum, Vodka, Gin, Whiskey, Tequila, Brandy, Liqouers (Triple Sec, Benedictine, SoCo, Bailey's, etc etc etc)

Beer: Black & Tan
Coke: Whiskey, Vodka, Rum
OJ: Vodka, Rum
Gin: Gin & Tonic, Gin & GingerAle or 7&7

I wouldn't be surprised if you could come away with this prop bet if you had to do it for a month. There are a lot of obscure drinks that no one ever drinks anymore like a Boxcar or Gin Rickey.

Vodka and Cran, Vodka and Red Bull, White russian, Black Russian
and you've got all the girly-type drinks like a Walk Me Down, Sex on the Beach, Hurricane, Manhattan, Cosmopolitan, Mai Tai, Pina Colada, Banana Daquri blah blah blah.

And again...I don't even know anything about drinking.

Then you could start making up your own drinks like telling the bartender to make you a "Sam in a Sweater"
Bartender: "Ummm, WTF is that?"
"Well, you take 2 parts vodka, mix in some triple-sec, diet Cherry Dr. Pepper and a touch of cream and blend it with ice. Teeny umbrella garnish is optional. Do you have any curly/bendy straws at least?"

[the idea of screwing with a bartender and ordering a drink that you made up on the spot is borrowed from a novel]

Just remembered that the last time I went to LV I saw two girls with some weird tall specialty drink at the blackjack table which they had evidently gotten out by the pool. So you see somebody drinking something funky looking and ask "Excuse me...what is that you're drinking?" [which is what I actually did] and then say, "Awesome. I want one of the those!!"

Wow, appears I really hit a nerve with ya Bob. Sorry, didn't mean to offend.

I thought the idea had potential but have come to the same conclusion that although it could get annoying for the right price its relatively easy.

I'm still going to make it a point to order and drink as many different things as possible this trip.

However, I would take the 10,000 to 1 shot that you would make a mistake over 4 days and 50 drinks.

That's a worthwhile goal. For $1/drink you can experiment.

And a Manhattan is NOT a girly drink, Bob! It's one of my choices when I'm feeling ready to hit "the hard stuff".

Sounds good to me.
I mostly see 35+ year old 'cougars' ordering that particular drink but I'm not in LV and I wasn't exactly paying THAT much attention.

A Manhattan is bourbon, vermouth and bitters, straight up. It's certainly no girlier than a Martini, and James Bond drinks Martinis.

FWIW, no chance I could ever win this bet. I'd start out with good intentions, but seriously over 4 days my only chance would be carrying around a notebook. We're talking dozens and dozens of drinks here...I'd never make it without screwing up at least once and being like "well it's here, might as well drink it"

Well, 10k to 1 shot is worth almost any unlikely bet.

But I can easily drink 13 drinks a day over 4 days, no writing down and not repeat a single one. Especially if you consider different brands of beer and wine to be different drinks. Hell, even if brands are excluded, just types of beer/wine.

go in alphabetical order like someone suggested. Order those weird girl drinks for the Q/X letters.

I won't enjoy it as I tend to drink Miller Lite, Chivas, or good tequila, so stakes would have to interesting enough for me to take the bet. (of course, I'd insist on no limits on water, I drink ALOT of water daily).