The 8 Dumbest Things I’ve Bet On: Confessions of a Gambling Addict

But for American men ages 16-dead, August has one redeeming quality: Fantasy Football drafts. There are few things better in the world than cramming into an apartment or conference room with 11 other disgusting men and battling to see who can pick the 15 millionaire strangers that will score the most fake points throughout the season. The last couple years I've been in two leagues—my $500 ultra-competitive hometown league, and my $100 work league (which has girls in it). This year, I'm adding a third, a $200 auction draft league. I've never done an auction draft and have no clue how it works, so, obviously, I couldn't turn down the opportunity to sink $200 into one. It's a good investment.

Anyway, that's 800 fucking dollars on fantasy football this year, or roughly 15% more than I make in a week. I'm gonna make some woman very happy someday.

The realization that I'm spending essentially a rent check on fantasy football this year got me thinking: I've done some really dumb shit while gambling. But I'm not alone. You're reading this on BroBible, which means you're probably a normal bro like me, which means you bet on dumb shit too.

So here's a list for the normal bros—the guys who can't watch a sporting event without “making it exciting,” and who can't even sit through church without betting their buddy on the length of the sermon. Half of you will read this and think, “Wow Jimmy T, you're a full-fledged fucking degenerate,” while the other half will nod nervously in agreement while mock drafting on your other browser tabs.

8. Actors in Movies

A classic guy bet here. An actor pops on the screen, and you turn to your buddy and ask, “Isn't that the same guy from Jurassic Park?” If your buddy replies with any variance of the word “No,” (including “Nah,” “I don't think it is,” or “Ehhhhhhhh, not sure,” it's time to name your stakes. The bet's as good as confirmed. I was once on the “No” end of “Isn't Milton from Office Space the same dude from Dodgeball?” Fuck you Stephen Root. I want my $20 back.

7. Online Blackjack

You'd have to be a vile, pathetic, weak-willed loser to wager real money on online blackjack. Only an absolute sicko would trust some mysterious offshore company using a “random” computer algorithm that determines the outcome of the cards and your money.

I've done it around 30 times.

6. Sports You Have No Clue About

The usual suspects here include soccer, baseball (you'd be surprised how many people don't know a thing about baseball), and hockey. I bet on at least 10 NHL Playoff games this year, because the Los Angeles Kings goalie went to my college and because the Chicago Blackhawks had a black guy. I've seen roughly 1.73 periods of hockey in my entire life.

5. Humiliating Props Amongst Your Friends

If you have a group of 3-4 friends who are immature assholes with a decent sense of humor, chances are good that you'll bet each other to do humiliating things, both for entertainment and as a test of manhood.

Last summer at my friend's wedding, one of my friends bet me and another friend that we wouldn't go out on the dance floor and slowdance for an entire song while grabbing each other's asses. This was during dinner when absolutely nobody else was on the dance floor. The easiest $25 I ever made. Plus, it's not gay if there's money involved (said every first-time gay porn actor ever).

4. Humiliating Props Involving Women

Now we're getting stupid. No. 4 is the same concept as above, except you throw unsuspecting females into the mix. It's hard enough for men to pick up women, without having to say ridiculous things solely to entertain your jackass friends, but because innately we're all degenerate idiots, we like to make it even harder. Like the time I had to try and get a girl to come home with me by making up a pickup line that had to rhyme with some aspect of her outfit. “Hey glitter, you got Twitter?” “Tan pants like ya stance.” That night ended with me banging my own hand.

3. Activities Involving Strangers' Kids

OK, before you call the cops, let me explain. My friends and I had season tickets to UConn Men's Basketball for a couple years, and during most of the halftime shows, they'd have this game where two kids would race each other to see who could put on a full UConn uniform (including sneakers) the fastest, then make a layup on the opposite end of the court. I got free chicken fingies for days for being able to spot the more talented 10-year-old.

I gave this one the “strangers' kids” designation, because someday when I have kids of my own, I'll completely rationalize betting on them.

2. Super Bowl Box Pools

In case you don't know how these pools work, you buy a certain number of empty boxes before the Super Bowl starts and once the pool is filled, the token hot chick at your office picks 10 numbers (0-9) out of a hat to see which numbers go in which row/column. The outcome of the pool is determined by the last digits of each team's final score of the game. If you know anything about football, you know the best numbers to get are 0, 3, 4, 7, while 1 and 8 are tolerable, and every other number blows dick.

Here's a little tale from last year's Ravens-49ers Super Bowl. In one of the smartest decisions ever made by eight adult men in their mid-twenties, my friends and I decided to participate in a THREE THOUSAND DOLLAR PER BOX pool. Keep in mind I've never even cashed in one of these since ever, so I thought it'd be a good idea to wager a not-that-shitty used car on one box. But no, $3K isn't cool, you know what's cool? We got two boxes for a total of SIX THOUSAND FUCKING DOLLARS on the most random thing in the world. Did I mention I've never sniffed profit in these pools?

So we have a couple guys go the live box drawing and I get a text from one of them a half hour later saying something to the tune of, “You guys are gonna hate me, we got 5-5 and 9-9.” The final score was Ravens 34, 49ers 31.

1. Potpourri

These bets are so dumb and random that they don't even get a classification—just the Jeopardy! category that lumps together random shit. The bets are situation-dependent and are often made during spur-of-the-moment arguments, generally with alcohol playing a factor. Here are a few of mine:

  • I once bet a friend that in 50 Cent's “In Da Club”, 50 rapped “got a mil out the grill and I'm still on the grind.” My friend contested that it wasn't “mil out the grill”, but rather “mil out the deal”, as in he got $1M for signing a record deal. I was 15 years old, I knew grills were big in rap at the time, so I just went with it. (It's “deal.” —Editor.)
  • I bet that the cop stripper from American Wedding was a brunette. (She is not. —Editor.)
  • I bet my buddy Paul Walker that he could pick any girl in the entire high school and I could turn her into prom queen. I had my sister give her a makeover and she got contact lenses but she still lost, so I had to go to graduation naked.
  • I bet my current roommate that he couldn't stand in the middle of my bedroom and touch both walls at the same time. After all, I'm the one who lives in the room, obviously I know exactly how wide it is. The only thing easier than his successfully touching both walls is Farrah Abraham.
  • And finally, I was on the winning end of the absolute DUMBEST bet anyone has ever made. The year the Lakers signed Karl Malone and Gary Payton, a Laker fan bet me $50 that'd they'd go undefeated. There are EIGHTY-TWO games in an NBA regular season, and he expected the Lakers to win every single one of them. He adamantly defended the bet with one defiant line, “Who gonna beat em?” to which I replied, “Somebody. Somebody will.” The 2003-2004 Lakers started 5-0 but fell to the Hornets in game 6 in what would be a 26-loss season. So close, man. So close.

[Man placing bet image via Shutterstock]