[[http://www.fimfiction.net/story/2029/Trip-Of-A-Lifetime Trip Of A Lifetime]] is a ''WesternAnimation/MyLittlePonyFriendshipIsMagic FanFiction'' by Tailslover13. The story follows Josh Schwartz, a human from Earth who ends up in Equestria due to unknown circumstances. However, unlike traditional "Human In Equestria" stories, Josh has one very defining characteristic: he is a total JerkAss.

The mane six take it upon themselves to try and help Josh get accustomed to life in Equestria until Princess Celestia can send him back home. However, the fact that Josh doesn't even believe in love, friendship, or anything like that may prove to be a difficult obstacle to overcome. It gets worse when Josh is turned into a pony due to Poison Joke, making him even angrier.

No matter which way you look at it, if Josh is around, [[HilarityEnsues hilarity shall ensue]].

* AmusingInjuries: Even [[spoiler: getting pushed off a cliff and flattened like a pancake]] doesn't leave any lasting impressions on Applejack and Rainbow Dash. [[spoiler: Neither does the Mane 6 and their experience with the "Pinkieball".]]
* {{Backstory}}: Josh tells his to Zecora in chapter 8. [[spoiler: [[DarkAndTroubledPast It's not pretty.]]]]
* BerserkButton: Pretty much everything in Equestria for Josh.
** Chapter 33. Zecora shows Josh [[spoiler: her scrapbook of her and her family]], and he immediately becomes furious. But when she psychoanalyzes him and virtually picks him apart with her words and intelligence, he comes extremely close to ignoring his principle of [[WouldNotHitAGirl not hitting girls]] and [[WouldHitAGirl assaulting her]].
* CerebusSyndrome: The story starts out lightearted and funny, but with [[spoiler: the revelations about Josh's past]] and [[spoiler: his strange dreams]], it's slowly getting a darker plot.
* CharacterDevelopment: [[spoiler: Slowly but surely, Josh's JerkAss tendencies are decreasing more and more.]]
* CutenessProximity: Josh only stops being an ass when Apple Bloom shows up. He goes back to it literally the ''instant'' she's out of hearing range.
** He also finds himself having to ''consciously try'' to be a jerk to Fluttershy. He backs down when she gives him a cute look. Subverted in [[spoiler: Chapter 29, where he seems to go right back to insulting Fluttershy naturally]].
* [[spoiler: DarkAndTroubledPast: Josh has one.]]
* DarkIsEvil: Granted, he's not necessarily evil, but as a pony Josh's coat is a dark purple.
* DeadpanSnarker: Josh, as well as most canon examples.
* DidntThinkThisThrough: Though he didn't exactly have a lot of time to plan it, [[spoiler: Josh realizes after going through with his idea of how to get revenge on Pinkie Pie and Rainbow Dash that he didn't consider the possibility of the rest of the mane cast fighting back.]]
* EvenEvilHasStandards: More like "even jerks have standards", but same idea. Josh finds the pony world exceptionally girly, but refuses to refer to it as "gay", knowing that word isn't supposed to be used as an insult.
* {{Flanderization}}: Reading the first chapter or two, you'd have a lot of trouble thinking Josh becomes a complete jerk in later chapters. There doesn't even seem to be that much of a catalyst for it, either.
* ForegoneConclusion: [[spoiler: Chapter 11 is titled ''Deception Is Bliss''. This alone makes it easy to tell Josh is faking it when he starts apologizing.]]
* TheFriendNobodyLikes: Josh to the mane six.
** Well, he ''did'' try to be nice, at first.... before he promptly got laughed at and mocked for being the unfortunate victim of Slapstick Comedy.
* GoodIsNotNice
* JerkAss: Who else.
** JerkWithAHeartOfGold: He seems ''capable'' of being this, at any rate.
* NiceJobBreakingItHero: [[spoiler: Josh's horrifying rage in chapter 10 likely wouldn't have happened if Rainbow Dash hadn't been taunting him.]]
* OhCrap: Josh's reaction to [[spoiler: Applejack charging at him after he hurts Pinkie Pie and Rainbow Dash. Also his reaction before getting promptly smacked down by Applejack again in the sleepover, as well as Derpy after he made fun of her "condition".]]
* OnlySaneMan: Josh believes he is this, though so far ''none'' of the major characters can really claim this role.
* PinkIsForSissies: Josh hates the entire world of Equestria because of how pleasant it is. The mane six are ''very'' confused by this.
* ShipperOnDeck: Josh temporarily ships Rainbow Dash with Twilight to distract the latter, and later with Fluttershy just out of frustration. [[spoiler: And eventually with Applejack, which leads to him deceiving them to push them off of a cliff.]]
** The Cutie Mark Crusaders seem to be trying to ship Josh with [[spoiler: Applejack.]]
* ShipTease: So far, Josh has been shipped with all of the mane six, as well as Zecora, and even (very briefly and subtly) with ''[[HoYay Spike]]''. And knowing the author, sooner or later, one of these is going to become an actual relationship.
* TookALevelInJerkass: Josh gets even worse after becoming a pony.
* WhatTheHellHero: Twilight does this to Josh while he [[spoiler: twists Pinkie into a ball]], but he blows her off.