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This can mean many things. It is a large faggot, a small dickhead, or someone that is just asking for a nice good slap in the dick. These can also be found in large piles of shit, just dig deep down until you find some mcmaster student swimming. It is its own insult.

It is also used when someone tries typing "simpler" but their brain somehow cant process the motor skills required, and ends up slapping the keyboard like a fatass whale. Needs rehabilitation
Look at that simoler, such a fucking simoler.

or: Nice arm spaz u dumbass simoler.
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Simpler times 

Something that people often say when they talk about the past or something in the past, usually a few years back. The good old days when there were fewer things to worry about and less complex technology.
I remember hanging out with my old friends, playing Half-Life on the computer, and when Urban Dictionary was first created, simpler times!
Simpler times by BigBoi Gaming December 29, 2020
Related Words
American slang word for a dollar.
Associated with early 1900s gangsters.
"The guy's got more simoleons than all of us put together."
simoleon by D-S January 23, 2006

simolean 

The currency used in the popular "Sims" series of computer games by Maxis / Electronic Arts.

The § symbol is used to define the currency. The § symbol appears in place of $ when typed within the game when using a standard keyboard.

A simolean is presumably made up of 100 'somethings' but I do not believe that the fraction has ever been given a name. Simcent or Simolette perhaps?
That pink flamingo is worth §7 if you buy them in bulk.

Woohoo I just got §564 for a large supreme pizza.

Simolean 

A fictional currency used in some Maxis games, represented by the legal "subsection symbol," "§".

It is, perhaps, a reference to a Neal Stephenson short story, The Great Simoleon Caper, in which an online currency is developed called the Simoleon for use in "the Metaverse," a virtual, networked reality, as established in Stephenson's oeuvre.

It may simply be a reference, however, to an uncommon colloquialism.
I typed in "rosebud" into the cheat console and got a whole bunch of simoleans.
Simolean by The Grizzled Boor January 4, 2012
Dating back to 1896 and with an unknown origin. This word is slang for "dollar"
Gime me some simoleons. Need to get a smoke.
Simoleons by Aldana2008 October 20, 2008

simpler souls

those with 'stiff' (conservative?, slow-witted?) mental attitudes and tendencies, when faced with some situation requiring a 'tad' bit of imagination. (aka; 'walking of the "wild" side'/stretching' of the mind.

those quick to 'not get it', and/or walk away quickly, back to their minister, banker, bishop or momma!
when joe spit flaming alcohol out of his mouth, the simpler souls didn't 'get it'!!

the simpler souls quickly left, when our fart-lighting session began.

we trained wendy to fart and belch, but the simpler souls couldn't handle it!
simpler souls by michael foolsley December 6, 2011