Gladys and Maddie

It was a slow night at the MGM casino in Las Vegas when arguably the two most interesting patrons of the night walked in. Although their minds worked in similar ways they had about 70 years difference in age. Nobody in the entire casino expected that when the 80-year old woman on oxygen and the 10 year old girl popping bubble gum entered the casino as strangers they would leave as partners in crime.
The first one to walk up to the bar was the old woman with full hair whiter than fresh snow. She had been called many things; Lightning, Gladdie, Nerd, but the name on her New Zealand birth certificate was Gladys. The next one to walk up was red-haired freckled Maddie. Everyone knew her as Maddie, although she called herself Wonder Woman that one Halloween.
“What’ll ya both be havin’ this evenin’?” asked the bald, but fully mustachioed, bartender.
“Scotch,” replied Gladys.
“Kiddy Cocktail,” answered Maddie.
“On the rocks,” they both added in unison.
They both stared at each other for a moment; Gladys through her all black sunglasses hiding her eyes, Maddie through her pink lensed, butterfly covered Hello Kitty™ Fun in the Sun Sunglasses. Gladys turned the valve on her oxygen tank up, Maddie popped her gum; their nervous habits.
“Alright then. First drinks are on the house.” the bartender said as he returned with the drinks.
Without saying anything to each other or the bartender they both headed over to the black-jack table. Maddie bounced and skipped there, her Dora the Explorer™ flip-flops making the standard flipping-flopping sound, Gladys shuffling along in her orthopedic shoes.
When they both arrived the dealer was understandably confused.
“Aren’t you a little young?” he asked Maddie “And… aren’t you a little old?” he asked Gladys.
“Considering how high I bet, I wouldn’t be asking me that question.” was Maddie’s reply.
“Buddy… I’ve played….more games of…. black jack…. than you can ever… hope to.” Gladys slowly answered.
“Alright then...” the dealer sighed.
They had both been doing alright a few hands through the game, no one had lost more than a couple hundred, but then something very odd happened. Maddie felt a poke against her arm under the table. She grabbed at it and felt that it was a card. She glanced over at Gladys and was barely able to make out a wink beneath her sunglasses. Maddie decide to go for as she had only bet $200 and slyly switched one of her cards with the one from Gladys.
“Alright, dealer has 20,” declared the dealer.
“21,” replied both Maddie and Gladys.
“Well I’ll be darned! Isn’t that the strangest thing?” remarked the dealer.
“Heh-heh. Umm yeah, sure is weird huh? Well hold on a sec, I have to talk to my, umm… grandma! Yeah, I have to talk to her for a sec, come on Grandma,” Maddie nervously replied as she tugged on Gladys’ arm.
Gladys and Maddie shuffled and flip-flopped off to a corner where none of the casino staff could hear them.
“Look, lady, I know what you were trying to do before, and I agree,” said Maddie.
“Alright then…kid…Can you….count…cards?” Gladys said between huffs and wheezes of oxygen from her tank.
“Like nobody’s business; I’m the top Mathlete in my school,” Maddie coolly replied.
“Just to….clarify…we are…talking about….cheating, right?” huffed Gladys.
“Like nobody has before,” replied Maddie.
If there is one definite thing in that came out of that strange relationship, it’s that no casino lost more money than when Gladys and Maddie partnered up that night. They hit every casino in Las Vegas that night, even the small ones. Nobody’s sure just how much money they won, but Maddie was able to buy the entire Hello Kitty™ franchise and Gladys became owner of the Shady Oaks retirement village she had been living in. They still get together occasionally to bet a couple thousand dollars in a blackjack game.

It was a slow night at the MGM casino in Las Vegas when arguably the two most interesting patrons of the night walked in.

I think there should be a comma after arguably.
Comedies are hard to write, because people always expect them to be outrageously funny. This wasn't the most funniest thing I've read, but it made me smile a bit. You did a good job on describing the two main characters' appearances and personalities. I think you need to add a few more random meetings though. Good job for first time though.

“Buddy… I’ve played….more games of…. black jack…. than you can ever… hope to.” Gladys slowly answered.

You don't need to put commas after the ellipses'. And i also don't think you need to trademark those things.

Anyway to the actual story/idea, i tend to agree with Elle that it was a pretty good attempt and you definitely need a bit more in there. I also think that it seems unreal because if they go in together it all seems a bit suss and you should probably have them meet at the bar and act very nonchalant about it all until at the end you sum everything up. On that note i think the ending was a bit obiovus, but i did really like the final line.

Anyway it was a good attempt and like everything, needs another edit! Enjoy.

"It was a slow night at the MGM casino in Las Vegas when arguably the two most interesting patrons of the night walked in. Although their minds worked in similar ways they had about 70 years difference in age. Nobody in the entire casino expected that when the 80-year old woman on oxygen and the 10 year old girl popping bubble gum entered the casino as strangers they would leave as partners in crime."

This opening has a lot of potential. One thing I've learned from watching too much British comedy is that a big part of funny storytelling is a funny, potentially funny, or at least somewhat odd scenario, and you definitely have one of those here.

"The first one to walk up to the bar was the old woman with full hair whiter than fresh snow. She had been called many things; Lightning, Gladdie, Nerd, but the name on her New Zealand birth certificate was Gladys. The next one to walk up was red-haired freckled Maddie. Everyone knew her as Maddie, although she called herself Wonder Woman that one Halloween."

You do a good job describing your characters here, and you add some of the requisite wordplay, which warms up the reader's funnybone.

"“What’ll ya both be havin’ this evenin’?” asked the bald, but fully mustachioed, bartender.
“Scotch,” replied Gladys.
“Kiddy Cocktail,” answered Maddie.
“On the rocks,” they both added in unison.
They both stared at each other for a moment; Gladys through her all black sunglasses hiding her eyes, Maddie through her pink lensed, butterfly covered Hello Kitty™ Fun in the Sun Sunglasses. Gladys turned the valve on her oxygen tank up, Maddie popped her gum; their nervous habits."

Here is an example of my biggest issue with your story. In comedy, at least in my favorite comedy, a huge part of what makes it funny is silly dialogue, and yours is kinda sparse.

Overall, I think you have a great skeleton to throw some comedic meat on. Fill out the dialogue, and maybe add a hook to the story's end, and you'll be the next P.G. Wodehouse.

3/5

P.S. - I'm having trouble using quote boxes. I just end up with a giant box around everything and a series of smaller ones in places I didn't intend them to be. If I could get a little tutorial on 'em I'd be eternally grateful.