Never change, Fluttershy.  
Never change.

Now she’s a richest mare in Ponyville

@raw19  
Twilight Sparkle: Just like Cherrliee, Gilda, Chrysalis, Ember, Autumn Blaze, Rain Shine, most of Kirin  
Rarity: The other runway mares when she was a model.

@phoenixacezero  
Spike: She used her ‘Flutterguy’ voice. They had no chance.

@Brass Beau  
RD: Still, Fluttershy…scoring… hot mares.

@phoenixacezero  
Rarity: The former does tend towards the latter.

@raw19
 
@Brass Beau  
Alternate take  
RD: Not only did she win big, but she also ended up scoring with three showmares. Three…showmares.

@Neko Majin C  
Nope, she’s just this lucky.

I am sure this is Discord’s doing.

In hour, Fluttershy became a billionaire.

@raw19  
Twilight helps her give them away at the door while RD bangs her head against a wall.

@Brass Beau  
But she refuses to until everypony has an equal amount of chips.

@phoenixacezero  
The casino owner has been begging her to leave for an hour.

@Brass Beau  
Hour later, she surrounded by more chips.

Just leave the table Fluttershy. Go play roulette instead.

I wish i had it like that. Damn. lol

Apparently a side-effect of knowing The Stare is that you have a really, really good poker face.

Why, Fluttershy… Why? ;-)

@Frustration in Excelsis  

 
It’s both. There’s a well known pro at the table throwing hands because he thinks she’s cute. Everyone else is a drunken amateur.

@SPB2016
 
She learns from the best and is Luigi

@Background Pony #A16A  
Because he’s popular.

Why do this artist’s pictures always get so many comments?

Fluttershy wins by doing absolutely nothing

@Jryvn  
Another legendary gambler  
@Bobthedalek  
First Otakushy, now Pokershy.