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To 'whale' in a game or 'whaling' is a term for gamers or gambling addicts who spend a good huge amount of money on video games or casinos. Since a whale is huge and they pay hugely for gambling or gaming, you can see why this is a thing.

With gamers, microtransactions existed for them within free-to play games (e.g. loot boxes, in-game currency, booster packs, cosmetics, etc.), gacha-like games, mobile games, battle-royale games or anything along those lines.

Gamblers are people who whale tons of cash on slot machines, poker and other natures of casino games and gambling.

"Whales" was a phrase first used by video game publishers to describe their main customers who insufferably liked to gamble their money for in-game items.
Bob: "Hey, Dylan. Guess what happened: I convinced my mum to buy me V-bucks and I spent a heck load on Fartnite last night. So cool, dude."

Dylan: "That game is for toddlers. I see why you needed her to buy it for you. Because toddlers rely on their mummies, and you like to whale money within a crappy game, to buy things you don't need. Player Ultimate Battlegrounds is way better than your game."

Sarah: "Guys, guys, guys... come on. It's not that bad. I spend my free time whaling my student funds on Weeb/Grand Order to get the best units with Gacha hatchers and to be a better player, haha... I think I'm the worst than both of you combined."
Whaling by Taz (The Legend) June 28, 2018
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when a man uses his weiner as a harpoon to impale an obese woman
John's into whaling these days, looks for targets at Weight Watchers meetings.
Whaling by DJAD May 24, 2007
A competetition whereby two or more people go out with the purpose of sleeping with the fattest possible members of the opposite sex. The one with the highest weight total wins and multiple copulations count towards the total value.
Des Moines, Iowa is a great spot for whaling. Me and bob went out and I bagged a 350 pounder!
whaling by Sean S. December 9, 2003
To go to a bar and try to hook up with fat girls
My roomate loves to go whaling on the weekends
Whaling by tc123892 July 27, 2009
The act of having sex with a fat girl who's fanny flaps resemble the tail fin of a diving humpback whale.
"I don't understand why the Japanese like whaling so much. Have they got no taste?"
Whaling by Jack Jismouth August 1, 2009
Whaling refers to a sex act that mimics how whales mate. The female is face up, on her back, and many other males (possibly up to 10) will lie next to her and try to reach her genital region with their extremely long male organ. They first one to reach her vagina (i.e. the male with the longest dick) wins the procreation game! Also called “side doggy style” or “96-ing”.
Dude, I had such a wild night whaling last night with that chick and those other dudes. I even won the whaling competition because I had the biggest schlong!
Whaling by Mdogg77 January 9, 2021
Whereas sharking involves picking on one group of people to try and get with, whaling just involves opening ones mouth and letting anyone (or anything) go in.
#1: Mate, he gave up sharking ages ago he just opened his mouth and let that fat chick come on in.
#2: That's what whaling is for!
whaling by the.personator June 12, 2010