#118 Crazy bets

It’s cold, it’s chilly, it’s November.

That’s why was strange when my friend Jenn was dropping her daughter off at school last week and noticed a student wearing shorts. “Wait, it’s freezing out,” she said to her daughter while zipping up her jacket and pulling her hat over her head. “Does that kid have Hot Leg Syndrome or something?”

“Nah,” her daughter replied, pulling her backpack on and climbing out the door. “He just has a bet going with another kid about who can keep wearing shorts the longest.”

I laughed when she told me this story because it reminded me of my college days when crazy bets were standard. I bet my roommate Dee a dollar he wouldn’t eat a nacho chip covered in Crisco (I lost), I entered a Sideburn-Off on who could grow the scraggliest muttonchops in a month (I lost), and I bet my friend Gillian she wouldn’t race around our cafeteria at full throttle and slide headfirst into our punnily-named drink station “Thirst Base.” (I lost, and thankfully the chocolate milk on tap wasn’t harmed.)

None of these bets made sense but they somehow made sense at the time.

The best crazy bets are like that.

Because we aren’t here forever and crazy bets add laughs to our days and our weeks. So what are you waiting for, betting geeks? It’s time to shake hands and enter a Beard-Off, it’s time to drop five on who’ll catch the kickoff, it’s time to steel your gaze for the Staring Contest Standoff. Yes, it’s time spin in circles fifty times the fastest, it’s time to see who’s after-dinner burp can be the nastiest, yes it’s time to tell the naysayers that crazy bets aren’t dumb, because it’s time for us all to recognize they’re part of the World Of


Hello, Toronto! I’ll be touring the neighborhood all next week for The Book of (Holiday) Awesome launch. Hope to see you November 14th at Indigo Bay/Bloor, November 16th at Chapters Brampton, or November 19th at Chapters Oshawa!

46 thoughts on “#118 Crazy bets

  1. My friend Kellen was always our go-to crazy bets guy in college, because he’d pretty much do whatever … even if there were really no stakes at all.

    “I bet you won’t eat a whole tablespoon of salt without anything to drink!”

    None of that, “I bet you five dollars … ” or “I’ll do all your homework if you … ” … nope, ol’ Kellen was just happy to entertain us.

    I’m very relieved to have read that no chocolate-milk-on-tap stations were harmed during the making of your bet.

  2. Our son bet another kid in his Grade 5 class he would stay in the same clothes for the whole of three days of the school camp. He won. The look on his face when he told me about the bet, he clearly thought the whole idea was awesome. Was I happy about putting name tages on every single item of clothing and painstakingly packing it all lovingly, then having it returned clean and folded? You bet I was! Hardly any washing. Awesome!

    1. Haha I love that story. It encompasses everything about a 10 year old AND an awesome mom of a 10 year old boy.

      1. There’s a real shortage of children’s camping story-books AND YOU HAVE A CLASSIC right here! Beautiful:)

  3. A nacho covered in Crisco? EW! That does remind me of this one guy, Scott. In middle school he would eat just about anything for a dollar. Food off the floor? No problem. Paper? Sure. The longest this went on the more gross it got. The last thing he ate, I swear I’m not lying, is spaghetti off a dead bird. It made just about everyone present sick, except Scott for some reason.

    1. LMAO! I think I’d like this Scott cuz I was able to eat some weird stuff as a kid. Of course, even I draw the line at dead-bird spaghetti.

  4. Working in the Arctic, 72 degrees farenheit below zero, with a wind. A poker game broke out to pass the time in darkness. A final bet: the loser was to strip down to naked and stand outside for one minute. Now to those of you who live in San Diego, this kind of cold freezes skin in 10 seconds, snot becomes icicles and hence formed phrases such as, “frosted balls”!
    *One minute naked in this due north is like an eternity!!!
    I WON and I’m still fertile, unfortunately my friend claims Mr.Turtle has never come out again;)

  5. What the heck is “Hot Leg Syndrome?” Actually, I think my brother has that, since he prefers to wear shorts when the rest of us are layering up.

    Like Laura, I am relieved that no chocolate milk on tap was harmed. Ha ha “Thirst Base”. This term could also be used to describe Edward and Bella necking.

    1. haha.. “necking” takes on a new meaning there too..

      Poor Jacob is being left out of all the fun though.. I’m sure he wants to get to Thirst Base too.. (or whatever the werewolf equivalent would be..)

  6. I said I’d start my day with more loving-good-fun bets! Some of these entries are pure; nearly harmless hilarity! Almost all bets are on!!
    *I’ll bet* “Sir Neil Pasricha, In The Hood”, will NOT count down and NOT write all the way to Awesome #1.
    So then he can announce to the world, “I WON! I WON! I WON!”

    1. What’s the incentive? I don’t believe *we* could be enough!
      How’s about I start it off with a burrito- I heard Neil likes burritos!

    1. I know a guy who wears shorts all year and I’ve never even seen him in a jacket. I like being cold…but not THAT cold. I can go barefoot in the snow, but its not I’m going to stand out there forever like that.

  7. I love this one! I’m really big into making crazy bets.. however, I’m not at all like Laura’s friend Kellen – I’d never want to actually be the one eating the crisco nacho or running around naked and covered in chocolate milk.. (did I misunderstand what happened in that bet?)

    However, I am an excellent “market maker”.. when any two people want to make a crazy bet, I am particularly good at coming up with a betting structure, or odds, or specific terms that will make both parties SURE they are going to win and want to enter the bet.. At my previous job, this was a constant source of amusement for us, and it mostly centered around various food bets: whole pizzas, gallons of ice cream, the entire contents of a vending machine, etc..

    Crazy bets are the best!

      1. Freddo IS an excellent ‘market maker.” He said it himself. He likes to set up the SPREADSHEET to keep the both parties playing on his terms.

        1. My initial reaction here would be to reply with a “har har.. very funny.. make fun of me for my spreadsheets…”

          Except the fact is that I most definitely put ALL of these bets in spreadsheets. How else do you expect a guy to keep track of it all? :)

          1. Not quite sure Freddo, but that sounds like it could be good news! An organized bookie is someone everyone wants to have on their team :)

  8. LOL, the title of the Windows Explorer Tab when I have it open to this post is “#118 Crazy b…”

  9. I work in the dishroom of my campus dining hall, and just the other day a friend was working across from me on the other dishline and leaned over the plate piles and cup racks to say “I bet you 20 cents I can keep the conveyor turned all the way up to 10 for the whole shift” (we usually turn down the dish belt to make the worst of the rush manageable). Naturally this led to trading banter and heckling for the rest of our 3 hour lunch shift, which is exactly the kind of thing that makes work AWESOME!

    He pulled through the thick of the lunch rush on 10, by the way, and I turned over my 2 dimes.

  10. I am proud to say that I actually witnessed some of these wagers. I was fairly confident that Dee would eat that Crisco covered nacho, and I also knew that Gillian would slide into Thirst Base. I was just surprised that neither felt sore the next day.

  11. I just made a bet with my boyfriend and best friend their both different but the consequences are the same I have to do what ever they want for a whole day the one with my friend is the one who gets caught with the shortest shorts at school loses and they are the others worker for the day and with my boyfriend I have no idea what his should be but each others worker for the day wih this One I need Aton of help with

  12. I have a bet with my brother on these terms: If he becomes king of the world by the time he’s 50 I owe him a million dollars. Now I gave him 100,000 to 1 odds, do if he doesn’t do it I get $10.

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  19. A few from my past:
    -“I bet you won’t eat compost” (it was gross)
    -“I’ll give you a dollar to lick paint” (also gross)
    -“I bet you’ll sprain your knee if you jump off the roof of the shed” (only a twisted ankle)
    -“I bet you won’t cliff jump spread eagled” (I don’t recommend it)
    -“dare you to put out that candle with your tongue” (surprisingly, I didn’t get burned)
    -(skiing)”I bet you can’t do a tail grab off that jump” (not actually that hard)
    …. I was not a smart child. I was known for never turning down a dare or bet.

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