Skepper

A person who always expresses their skepticism in another person's ideas.

Billy-Dude, I think I am going to ask Jenny out on a date soon.

Jim-She would definitely say "No" but it doesn't matter because you will never ask her out anyway.

Billy-Wow, you are the biggest skepper I know, always raining on my parade!

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Skeppers

A Skeppy fan channel on YouTube;
A Skeppy simp

Person 1: Did you watch the new Skeppers video today?
Person 2: Yeah, I did