Proposition Betting - An Easy Way To Get Free Drinks or Cash
September 12th, 2007 by Jeremy EnkeThis blog seems to be all business lately. So let’s have some fun. Before you go any further, check out this crazy bitch. It just seemed like the right thing to post since I also have a gay flag on this page.
Anywho, on to more important stuff. As many of you know I love to gamble. Although gambling on poker, sports, or casino games can be fun, I personally get a lot more satisfaction doing proposition bets. In fact I’ll share my latest prop bet.
My good friend and neighbor John (the big dude in the middle) is such a die hard Green Bay Packer fan that this dumb ass made the following bet. If Green Bay has a better overall record than the reigning NFC Champion Chicago Bears, then he will have the pleasure of shaving my head with a dull razor. Damn, that could be cold this winter!
But here is the best part, If when the Bears finish up the season with a better record he will have to fly a gay flag outside his home for 1 week. Note to fellow gamblers……..Bet with your head and not your heart.
Okay, as you can see I have a lot of fun messing with friends and doing crazy proposition bets. Below however are my favorite proposition bets. These are great bets to make at bars with drunk buddies for either free drinks or cold hard cash.
If you use any of these in coming weeks and make a profit, please ship the customary 10% to me via paypal. Alright, here goes in order of my favorite:
1. The Circumference of a Beer Glass - This is a classic and you will win this all day long. (Don’t lie, you know you just went into your kitchen to grab a glass and try it out.)
2. 6 Saltines in a Minute Challenge - Okay this one is good. Eating 6 saltine crackers in a minute doesn’t sound that difficult, but believe me it is. I have only seen one person do this successfully. The problem is that saltines literally dry up all the saliva in your mouth and you are unable to swallow. When making this bet, you cannot allow the suspect to drink any water or liquids during the 60 second period. (Gay Video, but I didn’t have time to scour Youtube for a better one)
3. Break a Beer Bottle With Your Bare Hands - This is also a good one but can be quite messy. It really only works well at house parties or if you have a sink to do it over. Definitely not the most profitable prop bet, but it does work.
4. Open a Beer Bottle With A Piece of Paper - Again, not as great as #’s 1 & 2, but it will trick most people. Good luck finding a sheet of 8×10 paper at the bar.
I actually have many more, but these are my favorites. If you have some good ones, please post in the comments. The first one I have actually found to work the best. Happy Gambling!


I suppose an “About Me” page is where you would expect to read a third person professional write up on myself. Hmmm…. well that’s not really my style, so I’ll just go ahead and tell you “about me” in my own words.












September 12th, 2007 at 1:43 pm
Flying a gay flag for a week. That should go over great with the neighbors. My next prop bet I am going to ask for your advice.
September 12th, 2007 at 2:37 pm
Being a Packer fan and having a gay flag flying in the yard for one week is still better than being a Bears fan - he already wins.
September 12th, 2007 at 2:58 pm
Oh Snap, apparently you have been drinking the Kool-Aid as well. Being a Packer Fan can’t be healthy for anyone.
This song may become popular again later this year.
http://www.youtube.com/watch?v=SHtkzAwG9iE
September 12th, 2007 at 3:19 pm
hey jeremy,
Chris rocker called, he wants to know when you are officially leaving your wife and coming out of the closet.
September 12th, 2007 at 3:20 pm
I used to have that on VHS, haha
September 13th, 2007 at 6:44 pm
Hey Rockon,
When I come out of the closet, it will probably be the one in your bedroom.
Your wife never knows when your going to get home. You make things so difficult for us.
See the chalice on top of the page…… Your wife fills it for me while you are at work.
September 15th, 2007 at 3:42 pm
Your post reminded me of the legendary Titanic Thompson, a golfer/gambler, who once bet somebody he could drive a golf ball 500 yards - on a frozen lake!
Here is a link to the BBC series which is the source of many videos about Hustling:
http://www.bbc.co.uk/bbcthree/programmes/real_hustle/
September 15th, 2007 at 3:54 pm
Umm…and maybe the Gay Flag should be in front of *your* house?
The “crazy bitch” you linked to in the first paragraph is actually a *guy* by the name of Chris Rocker, who is a “performance artist,” and bills himself as the most popular person on MySpace…or words to that effect.
September 18th, 2007 at 11:55 pm
Man.. All you guys that posted responses seemed to notice, was the fact that there was a Gay flag, did the rainbow colors catch your eyes? Maybe make you rethink your sexualities? JE was maybe trying to be funny? Maybe you guys are giant douches? I think I’m on the right course here…
September 28th, 2007 at 4:46 am
Or you could always walk up to every person in the bar and say “I bet ya a drink I know where ya got ur shoes…”
If they take the bet, u say “ya got them on you’re feet!” and enjoy your free beer!
November 12th, 2007 at 7:32 pm
[…] of Ron Turner & co., I am going to lose a crazy prop bet and have to get my head shaved this New Years Eve. <————tape delayed on […]