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Trial-Period Dating

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A common set-up in the romance genre, this trope covers when two characters date with an explicit deadline or for a pre-determined finite period of time to see if they are compatible. Typically this is done because one of the parties does not know whether or not they actually have romantic feelings for the other. Instead of accepting a rejection, the Love Confessor asks the confessee to give dating a try for a few weeks to allow the confessor a chance to properly woo them with the hope that by the end of the trial, the confessee has developed feelings for them and wants to continue dating. Frequently, the Love Confessor will frame this proposition as a challenge ("Give me one month to win your heart and if I fail, I'll leave you alone forever"). Regardless, the mechanics of the trope remain the same: one of the two sets an end date for their relationship as part of the condition to even start dating in the first place.
The Will They or Won't They? question inherent to this trope is the source of the dramatic tension, made ever more real because of the ticking clock on the whole thing. It forces a confrontation between the two about their feelings and a resolution on the relationship for better or for worse, averting No Romantic Resolution in the process. The pair is also likely to have some conflict or confusion about what should/shouldn't be included in the trial as far as physical affection goes; after all, if the trial is to be an effective gauge of compatibility, why not actually do what a real couple would, physical affection and all? Rife for Belligerent Sexual Tension, but can also be played straight and relatively drama-free for more naturalistic stories. And even when the love interest decides to reject the proposer at the end of the trial, it's rarely for long, leading to a Break-Up/Make-Up Scenario and eventually a Relationship Upgrade.
Sister Trope to Fake Relationship, though there's no deceit in this relationship and the end goal (at least for one of the involved parties) actually is to date their partner long-term. Also compare Test Kiss and the romantic version of The Bet. Arranged Marriage might overlap if the engagement period has a firm end date and is non-binding. Can also overlap with a downplayed version of Pity Sex, if the person being asked out only agrees to the trial because they feel too bad to turn their suitor down. See also Speed Dating and Forever Fling, in which two people only date for a short period of time due to factors outside of their control, then separate and reconnect later in life. Not to be confused with Testing the Love Interest, which usually shows that a character is in love with the person they aren't dating.
Note: Full context examples must explain the arrangement by including the enforced duration of dating.
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In the Clear Moonlit Dusk: Yoi is a Bifauxnen high school girl who has never really been approached by guys because of Attractiveness Isolation. Big Man on Campus Ichimura Kohaku takes an interest in her, and one day casually brings up the idea of the two of them test dating to help her get used to guys. Much to his surprise, she accepts and the next day she pulls out a Comically Wordy Contract to impose rules on the whole arrangement, the first of which is that they would only do it for a period between two weeks and a month. When the time to end things comes, they have both begun to develop genuine feelings for each other and decide to continue dating.
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The Lobster: A major part of the dystopian society of the film, in which every adult must be married. Singles are sent to a hotel where they must find a partner in 45 days or be turned into an animal of their choosing. Every guest at the hotel goes on a series of trial dates during their stay in order to find a "matching" mate.
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In Hokuou Kizoku to Moukinzuma no Yukiguni Karigurashi, after being proposed to by the the wife-seeking Count Ritzhard Salonen Revontulet who fell in Love at First Sight with her icy and dignified countenance, rather than rejecting him, retired career soldier Lieutenant Sieglinde von Wettin suggests to Ritz a trial marriage of one year to test for compatibility in the relationship and see if she can adapt to married life. The story follows how their romance develops.
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The Big Bang Theory: Leonard and Penny attempt a relationship "Beta Test" in the fifth season. They had previously dated in the third season but struggled to communicate because of their very different personalities, as Penny usually dated idiots and Leonard tended to date other academics. Leonard proposed open communication instead of just hanging out, while also giving each other more time to modify unattractive behaviors. While open communication had its own struggles, it ended up working as intended as they became more familiar with each others' preferences. Notably they didn't start having sex again and consider themselves fully back together until about six months later.
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365 Days: Massimo Toricelli, an Italian mob boss, kidnaps Laura, a Polish sales executive vacationing in Italy who Massimo saw on a beach in a hallucination a year ago and fell in love with. In the most aggressive and one-sided form of this trope, he tells her he's going to hold her captive for 365 days in order to make her fall in love with him, but that if she doesn't at the end she's free to go. Amazingly, in some combination of Fetishized Abuser and All Girls Want Bad Boys, this works.
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Black Mirror: In "Hang the DJ", this is enforced seemingly as part of a Bureaucratically Arranged Marriage. Under "The System", people are assigned partners to date but are told exactly how long the relationship will last. Frank and Amy are given only one night to be together before they must part ways. It's revealed it is all a part of a dating simulation that aims to discern which people are best fit to be together. Those who seek to defy the system and try to escape, as Frank and Amy eventually do, are actually the most compatible.
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Sports Night has a variation in its second season. Dana and Casey have had UST during their first season after his divorce (and even though she was dating Gordon). They finally have a Big Damn Kiss in "Special Powers", but by the following episode, Dana goes to a bachelorette party and realizes the bride-to-be is marrying the only person they ever dated - and when Casey did that before the series it ended in a nasty divorce. She returns and tells Casey she wants him to see other women for six months so that he's sure about her, and then they can get back together. Unfortunately for Dana, this backfires, as Casey no longer seems interested in her, and she realizes she made a mistake. The two do become friends again by the end of the season.
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Boy Meets World: Commitment-phobic Shawn implements a version of this trope in the high school seasons, where he has a 2-week rule in which he does not date any girl longer than 2 weeks and does not date the same girl twice, regardless of how he feels about them, to avoid getting hurt. This all changes when he realizes the mystery girl he's fallen for solely from the contents of her purse is Angela, a girl he's already dated and broken up with, something Cory had previously berated him for because of how well-suited they were for each other.
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Digger: The wombats are so pragmatically minded that their standard marriage contract has a fixed term with the option to renew.
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The Titan's Bride: Ordinary High-School Student Koichi is summoned to another world called Eustil to be the bride of Caius, the prince and future ruler of Tildant, land of the titans/giants. Due to a prophecy that promised destruction should Caius marry someone from his own world, he had to summon someone from another and that just happened to be Koichi. Koichi is, naturally, against the whole idea. Caius then proposes that Koichi gives him a month to make Koichi fall for him; should he fail, he'll send Koichi back to his own world. Koichi accepts.
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A Condition Called Love: Oblivious to Love Hotaru is baffled and initially turns Serial Romeo Hananoi down when he confesses his love to her and asks to date her after talking to her for the first time yesterday, but after she sees how much effort he puts into getting her to fall for him, she proposes that they date until Christmas in a few weeks, so she can find out if even she can fall in love just like everyone else.
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In Seven Days (2007), popular student Touji Seryou goes out with every girl who asks him out, but only for the duration of seven days. The plot revolves around the trial dating between him and another male student, who asked him out on a whim to see how he would respond.
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In Date Me, Bryson Keller, Bryson is dared to go out with someone new each week, namely the first person who asked him out on Monday morning and continues to do so until Friday afternoon. Since he never specified the suitor's gender, fellow male student Kai asks him out. After their Big Damn Kiss on Friday, Bryson calls off The Bet and they start going out for real.
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The following is a list of statements referring to the current page from other pages.

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Dating Tropes
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Flirting and Courtship
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Narrative Devices
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Trial-Period Dating
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Trial-Period Dating
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Trial-Period Dating
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Trial-Period Dating