History Characters / YoureTheWorst

->'''Played by''': Creator/ColleteWolfe

-->'''Jimmy''': Edgar, I think I know something about [[TheHerosJourney Cambellian storytelling]]. Ferris is TheHero. Creator/JenniferGrey is the {{foil}}. Principal Rooney is TheFool. ''Sloane'' is the {{sidekick}}. Cameron's the ''[[{{Villains}} villain]]''.

** EvilIsSexy: [[ConversedTrope Conversed]] InUniverse, with Gretchen admitting that Paul's new look is oddly hot.

* EndearinglyDorky: His relationship with Amy in season 2 is pretty cute, and apparently his goofy personality was one of the things that attracted Lindsay to him.
* EvilMakeover: In Season 4, he gets one of these, with a slicked back hair-do, new glasses, and more slick wardrobe. He ditches part of it at the end of the season after realizing he's fallen into a pretty toxic crowd though.
** EvilIsSexy: [[ConversedTrope Conversed]] in universe, with Gretchen admitting that Paul's new look is oddly hot.

* LovingAShadow: WordOfGod is that Paul sees Lindsay as that "hot fun girl" he could never get with in high school and his attraction to her is rather shallow as a result. This, combined with his desire for a family of his own, blinded him to the numerous signs warning him that he and Lindsay were just not right for each other.

* ParentalNeglect: In "The Seventh Layer", he reveals that his parents weren't always able to care for him fully due to having him at an older age than normal and not having the energy for it. His ''nephew'' was basically like a big brother figure who helped out in raising him.
* PracticallyDifferentGenerations: To the point that least one of Paul's siblings had a son who was like more like an uncle to him that the other way around.

* TookALevelInJerkass: After divorcing Lindsay, he becomes a lot more spiteful and mistrusting of women. Then again, it's hard to blame him. However, after a JerkassRealization, he straightens back up.

* FatalFlaw: She's almost pathologically selfish and self-centered. It is clear this is a family trait and we come to learn after meeting their mother that her and Lindsey both have a FreudianExcuse.

* DemotedToExtra: Makes fewer appearances over the course of the series, and only appears once in Season 4.
* MinorLivingAlone: His mother abandons the family and his father is barely around and just gets drunk all the time.
* ParentalAbandonment: As of "Bad News: Dude's Dead", he's twelve (maybe thirteen) and living alone in his house.

* TagalongKid

* ADateWithRosiePalms: On several occasions. Despite his best efforts, however, he can't while Gretchen's watching.
-->'''Jimmy''': You're not going to ruin this for me.\\
'''Gretchen''': Good.\\
'''Jimmy''': This is gonna happen.\\
'''Gretchen''': Glad to hear it.\\
''({{beat}})''\\
'''Jimmy''': ''Dammit!''\\
'''Gretchen''': Ha, I win!

* GirlOnGirlIsHot: His [[ADateWithRosiePalms response]] to the idea of Gretchen and Dana "hugging" certainly indicates that he is of this opinion.

* EndearinglyDorky: His relationship with Amy in season 2 is pretty cute, and apparently his goofy personality was one of the things that attracted Lindsay to him.

* BirdsOfAFeather: With Amy.

* ParentalNeglect: Not exactly full-on negligence, but in "The Seventh Layer" he says that his parents weren't able to care for him fully due to having him at an older age than normal. His ''nephew'' was his ParentalSubstitute.

'''Gretchen:''' Hmmm... I know Louis Armstrong... [[WesternAnimation/ToyStory Buzz Lightyear]]... for some reason Kurt Loder is coming to mind...\\

* MeanBrit: Condescendingly critical, ego through the roof, and snarky as hell.

* IllBoy: In the second and third episodes of season 3, after Lindsay stabs him.

** In the series finale, Gretchen finds out that Edgar told Jimmy not to marry her. She confronts him and gives a ReasonYouSuckSpeach, lampshading that “in times of extreme assholishness, letting you live with him was the sole humanizing thing about Jimmy.”

* StepfordSnarker: She has clinical depression and a razor sharp wit. She even initially refused getting treatment because she didn't want to "lose her edge".

* WellDoneDaughterGirl: She's so scared of disappointing her parents that she presents a largely fabricated alternate life and personality when in their presence. When Jimmy [[CallingTheOldManOut calls them out and says they don't know Gretchen at all]], she's both furious and terrified.

* IShallTauntYou: She notices that Lindsay and Edgar's ditzy Trivial Pursuit answers are annoying Jimmy (who is sitting on the other side of the room with his laptop), and she deliberately turns it UpToEleven during her turn.

** Season 4 has started to deconstruct this - Jimmy is repeatedly shown to not consider how his actions affect (if not downright hurt) other people, and [[spoiler:abandoning his friends and disappearing for three months]] has greatly strained his relationships with them and [[RealityEnsues it's clear it'll take way more than just a simple apology to make things right]].

* NoCelebritiesWereHarmed: He's apparently based on Tyler, the Creator.

* {{Cuckold}}: In Season 3, he lets Lindsay sleep with other men to make her happy, but is clearly disgusted with it.

[[folder:Gretchen Cutler]]
[[quoteright:344:https://static.tvtropes.org/pmwiki/pub/images/gretchen.jpg]]
->'''Played By''': Creator/AyaCash

A cynical and incredibly reckless music PR executive. Despite not being into relationships or monogamy, she decides to give things a shot with Jimmy when they become closer together.

* TheAllegedCar: Her old Honda. We don't get a really good look at the whole thing in daylight until "Fix Me, Dummy", but it is impressively destroyed. Judging by what was visible in the flashback in "Constant Horror and Bone-Deep Dissatisfaction", it was an alleged car even before she crashed it.
* AntiHero: At best. Gretchen is unsympathetic toward others' problems, snarky, dysfunctional to the extreme, and downright ''vicious'' on occasion.
* ArtisticLicenseAnimalCare: In "Fists and Feet and Stuff", she equates herself and Jimmy to two pit bulls who would kill other dogs but are "couch buds" with each other because fighting would result in mutually assured destruction. In reality, if you have two dog-aggressive pits (or any breed), they absolutely will try to kill each other.
* AwLookTheyReallyDoLoveEachOther: Gretchen and Jimmy are endlessly snarky, constantly deny and mock the concept of having feelings, and both react to Paul's definition of love (putting someone else's needs above your own) with "ew", but it just makes their sweet moments all the more heartwarming.
* BigEater: Like Jimmy, she takes full advantage of [[SupremeChef Edgar's masterful cooking]]. How she maintains her figure is a mystery.
* BiggerIsBetterInBed: Subverted. In "PTSD", she sleeps with an ex (a barista nicknamed "Venti"), but her offhand comment about his [[GagPenis size]] is really more to mess with Jimmy than to imply that "Venti" is actually good at sex.
* BirdsOfAFeather: She and Jimmy have a ''lot'' of significant personality differences, but their shared snark and mutual distaste for relationships is the only reason theirs works.
* BlatantLies: A storm of them in "Finish Your Milk".
** She tells Jimmy that she's flying home to "parental purgatory", when in fact her parents are coming to LA to visit ''her''. When Jimmy learns that she's still in LA and finds her at the museum, Gretchen recruits a couple of total strangers to play her parents.
** She tells her parents that she runs PR for Josh Grobin (definitely not anyone named Shitstain), that Jimmy is from the fancy part of London (he's from the bad part of Manchester), that they met at an animal-related charity fundraiser, and that Jimmy is a very popular and highly-regarded novelist with a movie in the works.
* BreakHisHeartToSaveHim: In "Other Things You Could Be Doing", Gretchen tells Jimmy that she's permanently broken, he ''shouldn't'' be okay with that, and he deserves to go be happy with someone else. [[spoiler: It's not a lie that she doesn't feel anything (depression does that), but her tearful "You stayed" when she wakes up to find him in the pillow fort with her at the end makes it clear she didn't really want him to leave forever]].
* CallingYourOrgasms: PlayedForLaughs in "Try Real Hard", the season 3 premiere.
-->'''Jimmy''': Why do you always announce it?\\
'''Gretchen''': What?\\
'''Jimmy''': You always announce it.\\
'''Gretchen''': I do?\\
'''Jimmy''': Always.
** She wants everyone to be aware that she has the floor.
* CharacterDevelopment: She starts to become more open with her emotions through the third season when [[spoiler:Jimmy stays with her despite her depression. She's even started taking medication, and is beginning to address her problems in therapy despite extreme resistance and anger at first]].
* ComicallyMissingThePoint: This exchange during her first therapy session walks the line between comical and sad.
-->'''Therapist''': Talk therapy combined with medication is the best long-term plan for managing depression.\\
'''Gretchen''': You mean beating depression.\\
'''Jimmy''': ''Winning'' depression.\\
'''Gretchen''': I like that!\\
'''Therapist''': That's not a thing.
* ConsummateLiar:
-->'''Gretchen''': I'm a giant liar, always have been. I told the Spice Girls I was dying of brain cancer to get free concert tickets.
* CryIntoChest: [[spoiler:At the end of "Other Things You Could Be Doing", when she wakes up to find Jimmy in the pillow fort with her]].
* DeadpanSnarker: Snark isn't quite as pervasive in her dialogue as it is in Jimmy's, but she’s similarly proficient with it.
* DespairEventHorizon: She appears to hit it in "Other Things You Could Be Doing", convinced that she "ran out of time" to overturn her depression and is permanently broken.
** DespairSpeech:
-->'''Gretchen''': I'm scraped out. I'm that car we put on Mars, flipped upside down so the sun can't reach my solar panels. I've always been able to flip myself back over, but I ran out of time. This is how I am now.
* DisproportionateRetribution: She informs Lindsay in the pilot that if she gets her real estate license, Gretchen will [[BreastAttack stab her in the tits]] (albeit likely in a comedic manner). In the season 1 finale, she threatens to punch Lindsay in the ''[[GroinAttack clit]]'' if she ever tries to kiss Jimmy again.
* DrowningMySorrows: Perhaps most evident in "There Is Not Currently a Problem". She is in the middle of a ''bad'' depressive episode and unable to get out of the house, so she tries to deal with it by drinking literally all of the alcohol. And then giving everyone in said house a TheReasonYouSuckSpeech. Except Vernon because he's not even worth one.
* DrunkDriver: Got a DUI shortly before the events of the pilot because she sideswiped an off-duty cop while drunk and texting.
* EmotionlessGirl: Gretchen's depression is occasionally shown to cause intense periods of this. In "A Rapidly Mutating Virus", Gretchen apathetically lets Sam, Honey Nutz, Shitstain, and Lindsey get beaten up by three female gangsters before walking up to one of the attackers, leveling a gun at her head, and saying, "Run." Her expression never shifts from deadpan. She admits to Lindsay later that all she felt was ''bored''.
* EstablishingCharacterMoment: Stealing the blender from Becca and Vernon's wedding, and then throwing it into the bushes when she discovers it is not a food processor.
* FatalFlaw: Her walls of defense mechanisms. She does have a FreudianExcuse so it's understandable, but her desire to keep people emotionally distant to protect herself from disappointing them or not being good enough for them makes her either lash out or repress her own feelings whenever anyone gets too close for comfort.
* FieryRedhead: Her intense personality goes quite well with her dark red hair.
* {{Foreshadowing}}: She tells Jimmy that she's probably broken in "What Normal People Do", and the state of her apartment is pretty common for people who suffer from depression. TheReveal doesn't come until season 2, but in retrospect, there had been signs for a while.
* FreudianExcuse: While we don't see much of them, it's clear her screwed up family life has not helped her present day self. Her mother, Vanessa, in particular is a shallow and [[ItsAllAboutMe self-centered]] StepfordSmiler who never once tried to understand her daughter's mental illness and worried more about how it reflected on ''her''.
* HeIsNotMyBoyfriend: In "PTSD", Gretchen says that she and Jimmy are not a couple, looking deeply offended that Becca would suggest such a thing. Even after they agree to be exclusive, they avoid the boyfriend/girlfriend label for a while.
* HeroicBSOD: She has clinical depression, and from "All About That Paper" through "Other Things You Could Be Doing", she's in a ''very'' rough place mentally.
* HisOwnWorstEnemy: She can be badly self-destructive.
* HiddenDepths: A few of her less-obvious talents are revealed in "Try Real Hard" when Jimmy realizes he doesn't actually know that much about her and starts asking questions. She competed in the US Teen Nationals for showjumping (yes, Jimmy, in "horsery"), did ink work for a professional counterfeiter for ten months, is "generally spiritual" ([[InsistentTerminology not religious]]), and speaks fluent Spanish.
* HeterosexualLifePartners: With Lindsay (Gretchen is definitely not straight, but Lindsay seems to be).
* {{Hypocrite}}: She doesn't want to tell Jimmy [[spoiler:his dad died]] because she's disgusted by the thought of Jimmy crying or her having to offer emotional support. This after her extended HeroicBSOD in season 2. Another line in "Equally Dead Inside" from season 1:
-->'''Gretchen''': For a second I thought he was going to cry, and I was like that's it, I'm never going to be able to have sex with him again.
* TheImmodestOrgasm: In "Try Real Hard". Her "you were so quiet" comment suggests that she's not always alone in this.
* InsaneTrollLogic: In "Fix Me, Dummy", when she's mad at her new therapist.
-->'''Gretchen''': You said there were things I could be doing, insinuating that I could have fixed myself at any time. That is invalidating my story. It is tired, it is patriarchal, and it is rape-culturey! You are basically a ''rape apologist''.
* InsistentTerminology: She's ''generally spiritual'', not religious. Also, she is throwing a ''party'' in "Born Dead", not organizing a get-together.
* IShallTauntYou: She notices that Lindsay and Edgar's ditzy Trivial Pursuit answers are annoying Jimmy (who is sitting on the other side of the room with his laptop), and she deliberately turns it UpToEleven during her turn.
-->'''Lindsay:''' (reading from card) Who was the first man in space?\\
'''Jimmy:''' ''Easy''.\\
'''Gretchen:''' Hmmm... I know Louis Armstrong... [[WesternAnimation/ToyStory Buzz Lightyear]]... for some reason Kurt Loder is coming to mind...\\
'''Jimmy:''' (standing up) ''Yuri Gagarin!'' It was [[PunctuatedForEmphasis Yuri. Gagarin.]] Louis Armstrong was a jazz trumpeter, Buzz Lightyear is a ''cartoon'', and Kurt Loder was a VJ for MTV, about whom the only connection to space travel is the fact that the network's logo was a man in a space suit!\\
(Jimmy sits back down, game continues)\\
'''Edgar:''' Charles Dickens wrote this novel about the plight of street urchins.\\
'''Gretchen:''' (staring directly at Jimmy) ''Annie''.\\
'''Jimmy''': ''Wow!'' (slams laptop shut, stomps out of room)
* LikeASonToMe: She makes jokes of this nature about Sam, calling his group her "dumb rapper babies".
-->'''Gretchen''': Look, I love my client like the black son I aborted in high school.
* LineOfSightName: In "Finish Your Milk", she makes up an excuse this way to prevent Jimmy from meeting her parents, in a clear ShoutOut to ''Film/TheUsualSuspects''.
* LoveMakesYouStupid: "The heart is a dumb-dumb."
* MotorMouth: In "Crevasses", when a department store employee asks what she needs to buy.
-->'''Gretchen''': ''Everything''. I just moved in with my boyfriend and I don't have any stuff. Except for a food processor and like nineteen ''thongs''. Because of course at first I was like "I am not wearing ''that''", but the patriarchy has convinced us that visible panty lines are unacceptable so I've just grown used to the feeling of a fabric rope against my actual asshole all day. Oh yeah and even if I did have all of this stuff there's nowhere to ''put'' it, because I'm not convinced this guy actually wanted me to move in with him, because I'm an irresponsible monster who burned down her apartment with her ''vibrator''.
* NightmareFetishist: The only one of the main four to actually ''enjoy'' the extreme haunted house in "Spooky Sunday Funday".
* NoMedicationForMe: Deconstructed. She has clinical depression but has never gotten any kind of treatment for it ("Shit no, I don't want to lose my edge"), despite the fact that she becomes entirely nonfunctional when it flares up. Refreshingly, antidepressants are treated as neither evil nor a magic cure-all. In an interesting spin on this trope, Gretchen is far more resistant to [[TherapyIsFortheWeak therapy]] than to actual pills.
* NoodleIncident: "[[OrphanedPunchline ...and that's how I got crabs from my guidance counselor]]."
* TheOneWhoMadeItOut: The Season 4 episode, "Not a Great Bet", plays with this.
* OohMeAccentsSlipping: In "Equally Dead Inside", when she imitates Jimmy's accent
-->'''Gretchen''': I listened to you blathering on about "ooh, me da".\\
'''Jimmy''': That's ''Irish'', dumb-dumb.
* PottyFailure: A combination of a nasty green health-food smoothie and uncharacteristic jogging results in her having to hose off her legs in a stranger's garden. Still less humiliating than accepting a marriage proposal that didn't happen and wasn't going to.
-->'''Gretchen''': I shit myself earlier, and that is only the ''second'' most embarrassing thing that has happened to me today!
* PuttingTheBandBackTogether: Subverted in "Born Dead". She invites four of her friends to a party, expecting to have crazy irresponsible fun like they used to. One has a baby, one is pregnant (Gretchen makes exceedingly unwelcome jokes about "getting rid of it" before being informed that this is an intentional pregnancy), and one is a born-again Christian and member of Alcoholics Anonymous. The fourth has nosedived in the other direction and is a total trainwreck who steals Jimmy's stereo when she leaves.
* TheReasonYouSuckSpeech: She unloads a gloriously vicious one on Jimmy in the pilot (funny and true and mean, his favorite kind of speech). And then in "There Is Not Currently A Problem", she does it to nearly ''the entire cast''.
* RunningGag:
** Stealing booze from every place she visits.
** Writing absurdly long texts.
* SarcasticConfession: Played with at the end of "PTSD" when she and Jimmy snark that they should just be exclusive if they're both so bothered by each other sleeping with other people. Gretchen has to clarify that they actually are both saying they want this and are not just being sarcastic anymore. Jimmy admits he lost track, but they are officially exclusive from that point onward.
* SanitySlippage: In the Season 4 premiere, [[spoiler:she's gone manic, [[{{Hikikomori}} holing herself up in Lindsay's apartment]] for the full three months since Jimmy left her on that hill back in "No Longer Just Us". Her self-destructiveness has gotten to the point that she happily bought crack from a neighbor]].
* SelfDeprecation: A significant element of her sense of humor.
* SeriousBusiness:
** In "What Normal People Do":
-->'''Gretchen''': This could end tomorrow, who knows. But until then, if there is ''any'' chance of breakfast and you do not wake me up? I will never touch your dick again with any part of my body.
** She and Jimmy have a screaming meltdown when they come upstairs in the morning in "Crevasses", because Edgar has left the house without setting up the usual Sunday Bloody Mary bar.
** Also in "Side Bitch" when Jimmy accidentally takes her to a water bar, the concept of which offends her on a very personal level
-->'''Gretchen''': I am going to go to the bathroom, and when I get back you are going to take me to a real bar and give me cheap whisky until I forget about that time I became unable to have sex with my boyfriend because he took me to a ''bar that only serves water''.
* SkewedPriorities:
-->'''Gretchen''': What am I gonna do, just bend down and wash my legs? Who has the time?\\
'''Jimmy''': Yesterday, you spent two hours ''drawing a maze''.\\
'''Gretchen''': Yeah. And how do you think I had time to draw that sick-ass maze?
* SleepCute: Occasionally with Jimmy. In "Try Real Hard", the sleep cute gets ruined when his phone falls out of his hand and lands on her face.
* SmokingHotSex: She and Jimmy occasionally share a post-coital cigarette on the steps outside.
* StepfordSnarker: She has clinical depression and a razor sharp wit. She even initially refused getting treatment because she didn't want to "lose her edge".
* ThisIsGonnaSuck: In "Fists and Feet and Stuff", after Jimmy's speech in her apartment about how important she is to him.
-->'''Gretchen''': Shit. We're gonna do this.\\
'''Jimmy''': Shit.\\
'''Gretchen''': Even though we both ''know'' how this ends. Whether in a week or twenty years, there is horrible pain and sadness coming and we're ''inviting'' it.
* TrashOfTheTitans: Her apartment is a massive disaster, which probably has something to do with her depression. [[NeatFreak Jimmy]] is horrified the first time he sees it. After she moves in with him, she seems to be able to keep her space under control, but she still needs help. And she still adamantly ignores the mail because bills are scary and she might find a check from her grandmother which would [[MoodWhiplash make her feel guilty for never calling her and then Gretchen wouldn't be able to get out of bed for a month]].
* WellDoneDaughterGirl: She's so scared of disappointing her parents that she presents a largely fabricated alternate life and personality when in their presence. When Jimmy [[CallingTheOldManOut calls them out and says they don't know Gretchen at all]], she's both furious and terrified.
* YouAreWhatYouHate: She fears that only people who secretly ''are'' sweater people fear ''becoming'' sweater people, "[[ArmouredClosetGay like how homophobes actually want all the dicks in their mouths]]."
[[/folder]]

[[folder:Jimmy Shive-Overly]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/jimmy_0.jpg]]
->'''Played By''': Creator/ChrisGeere\\\
''"I'm an adult. Do you know what that means? It means that I'm beset upon at all times by a tsunami of complex thoughts and struggles, unceasingly aware of my own mortality, and able to contemplate the futility of everything, and yet still rage against the dying of the light."''

A selfish and insensitive British writer living in Los Angeles. Jimmy excuses his insensitive behavior as merely "telling it like it is", but it's clear he has a nicer side buried deep underneath.
----

[[folder:Edgar Quintero]]
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/edgar_5.jpg]]
->'''Played By''': Creator/DesminBorges

Jimmy's housemate, an Iraq War veteran struggling with PTSD.

* {{Adorkable}}: It pops up when he's really enthusiastic about something. Specifically, his Halloween costume in "Spooky Sunday Funday", and his cheesy ragtime performance at the speakeasy in "The Last Sunday Funday".

* {{Adorkable}}: His relationship with Amy in season 2 is pretty cute, and apparently his goofy personality was one of the things that attracted Lindsay to him.

* YourCheatingHeart:
** Played with in "PTSD". Neither he nor Gretchen wants to admit they want an exclusive relationship, so they goad each other into sleeping with other people.
** From "Spooky Sunday Funday" through "Other Things You Could Be Doing", Nina appeals to him because Gretchen's [[HeroicBSOD depression]] is making her incapable of offering him any kind of support. He turns Nina down when she starts actively flirting with him, but almost sleeps with her at the end of "A Rapidly Mutating Virus" after Gretchen tells him to go away. [[spoiler:He and Nina stop at the beginning of "Other Things You Could Be Doing", and despite Gretchen telling him he should give up on her because she’s broken, he stays]].

* ReallyGetsAround: Before getting married, and [[YourCheatingHeart after realizing she's unhappy in her marriage]]. Becca calls it "cockaholism".

* YourCheatingHeart: In her own words, there's wife!Lindsay who supports her husband, and adulteress!Lindsay who just wants to [[ReallyGetsAround sit on everyone's faces]]. RealityEnsues big time in Season 3, where her "cockaholism" finally [[spoiler:takes its toll on her and Paul's marriage, and Paul aims to leave her with as little as possible in their divorce]].

* HiddenDepths: All over the place. Most recently, he was revealed to have extensive knowledge of ragtime music and its history.

* EmotionlessGirl: In "A Rapidly Mutating Virus", Gretchen apathetically lets Sam, Honey Nutz, Shitstain, and Lindsey get beaten up by three female gangsters before walking up to one of the attackers, leveling a gun at her head, and saying, "Run." Her expression never shifts from deadpan. She admits to Lindsay later that all she felt was ''bored''.

* PopCulturalOsmosisFailure: He's never seen ''Disney/TheLionKing''. Gretchen amuses herself trying to make him say song lyrics.

'''Gretchen:''' Did you just quote ''Disney/TheLionKing'' to me?\\

* BiTheWay: She instigates a threesome bringing in her "work wife" Dana when Jimmy is upset in "Equally Dead Inside". She mentions that she's always been terrible at interacting with girls, lamenting that she can't believe she finally made another female friend outside of Lindsay and immediately tried to bang her. Gretchen also flirts with and tries to kiss Nina, and in season 4 [[spoiler:has sex with her boyfriend Boone's ex-wife while blackout drunk]].

* HeterosexualLifePartners: With Lindsay (Gretchen is [[BiTheWay definitely not straight]], but Lindsay seems to be).

* BiTheWay: Expresses attraction to women but also sleeps with a gay gossip writer.

* BiTheWay: Aside from bedding a decent amount of women, he's also seen kissing Boone (who's male).

* FatalFlaw: Has two of these. First is his lack of consideration for the needs of others. The second one is his inability to self-reflect. Jimmy often gets called out for projecting his worldview and opinions on others, without caring about how that affects the people around him. Yet, he rarely takes those opinions into consideration and rarer still is he ever critical of his own behavior without prompting. This second flaw becomes ''the'' central issue in his relationship with Gretchen because she is often willing to move past or forgive him if he would just apologize, but that would take him admitting he did something wrong in the first place, which, again, requires him to reflect on his actions.

** In "There is Not Currently a Problem", he excitedly asks Gretchen (who is in the throes of a big meltdown) to give him a TheReasonYouSuckSpeech and gets disappointed when she says he's not worth one.