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Jill is a hot mess. It's up to YOU to navigate through a series of awkward moments that either leave her somewhat dignified or even hot-messier. That Moment When is an interactive comedy from Eko, starring Milana Vayntrub as Jill Stepanov, and created by Sandeep Parikh.

In season 1 (7 episodes), you make choices to help Jill pull her shit together before her 10 year high school reunion. Season 2 is on its way.

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That Moment When provides examples of:

  • Alpha Bitch: Stacey Defoe is characterized as this by Jill throughout the series, leading up to her appearance in episode 7, where she definitely lives up to it. She mocks Jill for being homeless, tells her that she's going to go after her ex-boyfriend, and then tries to humiliate Jill in front of everyone by giving her an "award" for "Person Who Traveled the Least Furthest to Get Here", announcing to everyone that Jill gets the award because she lives in her car.
  • Arch-Enemy: Stacey Defoe is Jill's. Several times throughout season 1, Jill mentions how horrible she is, and the importance of not looking bad at the Class Reunion because "she'll chew me up and spit me out".
  • Basement-Dweller: Jill's brother is portrayed as this. He manages to be even more of a manchild than she is. He lives with his parents, he whines constantly, he spends all his time sitting on the couch playing video games, and one of several possible bonus scenes is for him to try to eat an orange the way one would eat an apple, then call out to his mom that "this food is broken" and he wants some chips.
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  • Beauty Is Never Tarnished: Sometimes Jill's clothes or hair suffer a little from the events of the episode, but it never goes beyond Unkempt Beauty; and her makeup is always perfect, even when she's living in her filthy car.
  • Bedmate Reveal: The "bedmate" aspect is the premise of episode 7; the goal is to get to the "reveal".
  • Class Reunion: A 10-year high school reunion is the setting of the season 1 finale, which all the preceding episodes are ultimately building up to.
  • Creepy Child: The sick child in episode 6 seems to be the one running her household, with her father being more of a servant than anything else. She calls her bedroom her "ready room", speaks in Creepy Monotone, and is way too Wise Beyond Her Years. She gives off Diabolical Mastermind vibes.
  • Cruel Mercy: When Stacey tries to humiliate Jill in front of everyone at the high school reunion, Jill has three sequential choices for how to respond, each with an "angelic" option and a "devilish" option. If she picks only the angelic options, she first thanks Stacey for the "award"; then admits that it's true that she's been living in her car; then tells Stacey that she feels sorry for her for trying to ruin her night instead of just having a good time, followed by admitting that she wanted to do the same, and apologizing for that. By the end, everyone is cheering for Jill, and Stacey's petty nastiness has been thrown into full relief.
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  • Dirty Old Man: At the Class Reunion in episode 7, Jill's former English teacher tries very hard to hit on her and/or feel her up.
  • Easy Come, Easy Go: In season 1, the middle episodes end with Jill abruptly losing whatever she spent the episode fighting for. In episode 3, if she nails the interview with Brooke, she'll accidentally let the dog run off, and Brooke immediately revokes the apartment in anger. In episode 4, if she convinces Olivia not to fire her for playing sick, Olivia's boss shows up and fires her — and everyone in her department, including Jill — because she's also playing sick. In episode 5, if Jill convinces her parents to lend her some money, she suddenly decides to tear up the check and declare she'll figure things out on her own. These three failures culminate in her living in her car in episode 6.
  • Foe Romance Subtext: At the end of episode 7, it's strongly implied that Jill had a threesome with her ex-boyfriend Jack and her high school nemesis Stacey.
  • Grey and Gray Morality: Jill is no saint, but most of the people she's up against (arguably, even most of the people she encounters, period) aren't the greatest, either. In episode 3, Brooke is a self-important control freak with unreasonable standards; in episode 4, Jill's boss Olivia is pretty rude, and a hypocrite to boot; in episode 5, Jill's parents are vulgar and overbearing, while her brother demonstrates that it is in fact possible to be more of a manchild than she is; in episode 6, the sick child is actually a Creepy Child with Diabolical Mastermind vibes, and furthermore knew the puppy in her possession belonged to someone else; and in episode 7, Stacey Defoe goes out of her way to humiliate Jill.
  • Heel–Face Turn: If the Threesome Subtext / Foe Romance Subtext at the end of episode 7 is anything to go by, Stacey turned over a new leaf in quite a hurry.
  • Jerk with a Heart of Gold: Jill does some hilariously shitty things, but usually it's not out of malice. Sometimes it's out of recklessness or immaturity; sometimes it's out of sheer desperation to salvage a bad situation, or a purely amoral bid to get something she really wants or needs. When she's not driven by one of these, she's usually quite friendly and seems to want to do the right thing, for whatever that's worth. For example, after jumping through several hoops to convince her parents to lend her some money, she suddenly decides that she should just work things out on her own, and rips up the check.
    • Jerk with a Heart of Jerk: On the other hand, on the few occasions Jill actually does something kind or sweet, it's almost always because she gains something from it. (She buys her boyfriend an expensive jacket so he can help her look good at the Class Reunion; she compliments her mother because she needs to borrow money; she kills Stacey Defoe with kindness to make her look bad; etc.) As for ripping up the check, that was as much an act of pure impulse as anything else she does, and she immediately regrets it.
  • Lives in a Van: In episode 6, Jill is living in her car because she lost her chance at a new apartment, then lost her job, then decided not to borrow money from her parents. In episode 7, Stacey Defoe mocks her mercilessly over this.
  • Loser Protagonist: Jill is deliberately portrayed as a "hot mess" who "attracts awkward moments". First, she runs into a guy from her college days and spends the evening pretending she remembers him; then her boyfriend breaks up with her; then she tries to secure an apartment by surviving the owner's crazy interview, only to lose it when she accidentally lets the dog run out; then she's caught playing sick by her boss and is fired; then she has to ask her parents for money, only to rip up the check and decide to work it out on her own; then she's reduced to living in her car, and subsequently reduced further to knocking out a clown, stealing his costume, and sneaking into a party so she can steal the dog back from a sick child to regain the apartment; then she spends an evening trying to avoid utter humiliation from Stacey Defoe, dodge her creepy teacher's advances, and gain the approval of a theatre troupe, only to remember none of this the next morning because she drank so much. But even these are broad details that don't fully capture how pathetic or ruthless Jill can be in pursuit of her goals.
  • Nice Guy: For the brief amount of time we see him, Jack is mostly a kind and levelheaded person. When he breaks up with Jill, he does his best to be gentle with his criticisms. It isn't until Jill literally commands him not to go easy on her that he starts venting more serious frustrations in a harsher tone — and they're all pretty fair complaints. (She stayed home watching a TV show when she was supposed to be picking him up from the airport; she used their joint bank account to rent a cotton candy machine for a ludicrous amount of money; etc.)
  • Not Staying for Breakfast: Jill attempts this after discovering she slept with her ex-boyfriend Jack, but he comes out of the bathroom just as she's about to leave.
  • N-Word Privileges: See Refuge in Audacity.
  • Ow, My Body Part!: In episode 4, when trying to appear sick to her boss, one method Jill can use is to cry "Oh, my spleen!" When her boss then has to appear sick to her own boss, she attempts the same tactic.
  • Precision F-Strike: Each episode begins with an establishing scene with credits, followed by a woman's voice Title Dropping the episode and explaining your end goal. Every single one of these contains the f-word somewhere. Example: "That Moment When You Got Too Drunk To Remember Your High School Reunion. Help Jill remember what the fuck she did last night."
  • Refuge in Audacity: In episode 6, Jill impersonates a clown at a child's party. When questioned by the father (who's suspicious about her lack of clown makeup), she can claim to be a "classical clown", and will say "Honky honky honky!" to support this. The father protests that "honky" is a derogatory term for a white person, and Jill replies that classical clown practice is "firmly rooted in the civil rights movement". He buys it to the point that he's apologetic for questioning her. Then, when he jokingly says "honky", she retorts that only classical clowns can say that word.
  • Shout-Out Theme Naming: The main character's name is Jill; her erstwhile boyfriend's name is Jack.
  • Three-Way Sex / Threesome Subtext: Heavily implied in episode 7, which ends with Jack being revealed as the guy Jill slept with last night…only for Stacey to also emerge from the bathroom and declare what a "weird night" it was.
  • What Did I Do Last Night?: The premise of episode 7, titled "That Moment When You Got Too Drunk To Remember Your High School Reunion". Jill spends the episode recalling bits and pieces.
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