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Tear Jerker: Voltage Inc
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Pirates In Love
My Forged Wedding
Yuta's sequel, starting around chapter four, discusses the issue of long distance relationships, as Yuta is being asked to do a job in France, while the protagonist has just found a job she really loves and doesn't want to leave. The story ends with them having a sweet day-long date and promising to work hard both at their respective jobs and at their relationship, but it still hurts to see them parted.
Seduced In The Sleepless City
In Your Arms Tonight
In Ginnosuke's route, the protagonist makes up her mind to stand by Koichi, and Ginnosuke responds by bowing out and leaving the country indefinitely, he and the protagonist sharing a bittersweet farewell at the airport before his flight boards. All of this is already sad enough, but the real tear jerker comes afterwards, when Koichi - who has genuinely fallen in love with the protagonist and is doing his best to be a true husband to her - realizes that it's too late, and that her heart already belongs to someone else. As the protagonist apologizes in tears, he tells her that it's his own fault, and that if he'd loved and appreciated her sooner, he wouldn't have to lose her now.
Koichi's route is particularly hard on the protagonist (and Koichi once the Break the Haughty has started to set in) but the moment that takes the proverbial cake occurs after the protagonist, Koichi, and his mistress have an explosive confrontation at a company hiking trip. The protagonist — already suffering from the emotional strain of trying to keep her marriage together and enduring Koichi's cold attitude — gets lost in the nearby woods and eventually trips and falls. Instead of getting back up or finding her way back, as she would've done earlier in the story, she finally breaks down and isn't even sure if she's laughing or crying.
In Koichi's Another Story, after things really go south with the protagonist Koichi resorts to calling her at work at outright begging her to meet with him, promising to wait until she comes. She has no intention of showing up, and when it starts to rain an hour before the time he set, she's sure he won't be there either. Somehow, though, she ends up rationalizing her way into wandering out to the meeting place... and when she gets there, two hours after the appointed time, Koichi is there, standing in the rain.
Be My Princess
Love Letter From Thief X
My Sweet Bodyguard
In Subaru's route of the New Years side story, he and the protagonist end up meeting Goto during their New Years Day shrine visit, and accompany him to see a small waterfall... a place that Kazuki had introduced him to. He and Subaru spend some time quietly reminiscing about Kazuki. Throughout the conversation, Goto looks both fond and sad; before they part ways, he advises Subaru to always protect the protagonist even if she finds it annoying, and tells the two of them to always stick together. The encounter leaves the normally-confident Subaru shaken and subdued for the rest of the day, thinking about how easily that could be him, and about what he'd do if he ever lost the protagonist.
A Knight's Devotion
Every last one of the Normal Endings aside from Junya's has the protagonist and her guy acknowledging that they're in love with each other, only for the guy to gently but firmly explain that, for various reasons, he's decided that they shouldn't be together, and that it's better for them to remain strictly as co-workers and focus on business. In all such cases, it's painfully clear how much it hurts him to step back from their relationship, and the protagonist can only accept his reasons and try to find a way to deal with it.
Toranosuke's hits especially hard: he has to get himself drunk before he can bring himself to end things with the protagonist, and then there's the email that comes afterwards.
I haven't gotten this drunk in ages. To make it worse, I haven't slept in days... Do you know, I still can't sleep. I've been thinking about you and me. I think maybe if we'd have been in different companies, things might have turned out differently. But who knows... But thank you for everything. I'm still glad I got to meet you and I look forward to working with you still.
Ten Days With My Devil
Shiki, of all people, causes these by the boatload on the end of his route. He unexpectedly takes the protagonist away to see "the end of the world", which turns out to be a distant beach where the two of them watch the sun rise over the ocean. And then the other inhabitants of the Demon House show up to bring the two of them back. Turns out Shiki rewrote the protagonist's entry in the fate database to save her, which means he's broken two laws of the Demon Realm. The heartbreaking part is that everyone else is distraught over the turn of events, and snarky, growly, mistrustful Shiki is suddenly so very gentle with everyone about being okay with being wiped from existence because of his actions.
Shiki does it again on Kakeru's route: with Kakeru condemned to execution for his actions on behalf of the protagonist and her sister, helpless to save his friend or comfort the distraught protagonist, all Shiki can do is plead gently with the protagonist to accept him as Kakeru's replacement.
Kiss Of Revenge
Any time, on any route, when the protagonist asks her late mother's memory if it's okay for her to have a life and be happy. It's heartbreaking to witness someone so broken by circumstance that she thinks living for herself is a betrayal.
In an already fairly dark game, Issei's route will startle some tears out of you. The climax of the protagonist's revenge plot comes when she is invited to dinner at Issei's home. This is the perfect time to kill Issei, who the protagonist has learned was the doctor who made the fatal mistake in her mother's operation. She finds her chance when it appears Issei has passed out, and the protagonist has ready access to a knife. When she cannot bring herself to kill him, Issei reveals he was awake the whole time, and planned the dinner to give the protagonist a chance to have her revenge. He even encourages her to kill him, if it will give her peace.
A similar confrontation happens in Issei's Another Story, when he tells the protagonist he will kill himself if it will give her peace. It's pretty harsh for a game rated 12+.
Dreamy Days In West Tokyo
Class Trip Crush
In Homare's sequel, after the incident at study camp is all over and Homare and the protagonist have resolved the drama their relationship has been going through, life settles down to normal and they get back to focusing on studying for their exams... and then, the night before Homare's all-important university entry exam, his mother has a seizure and has to go into emergency heart surgery, from which she has at best a fifty-fifty chance of recovery. Mrs. Midorikawa asks to be taken off anesthesia long enough to talk to her children, who are all the more distraught at what she clearly intends to be her last words to them if the surgery doesn't go well. Homare is so devastated that he breaks down and cries for the first time since his father died... and he still has to go take his exam the next morning, because if he doesn't he'll lose his chance at getting the scholarship he needs to go to college.
Our Two Bedroom Story
Midway through Shusei's sequel, at the end of a pleasant day out just having fun together, Shusei's efforts to be patient and supportive start to slip - on a sightseeing boat, backlit by the sunset, he wistfully asks the protagonist if they shouldn't just stay on board the boat and sail off together somewhere far away, where (it's implied) they'd be able to escape the threat of society's judgment and all of the other things that are weighing so heavily onto their relationship. It's one of the first major signs of just how much the situation is hurting him... and because of the noise of the wind and surf, she doesn't fully hear him.
alternative title(s): Pirates In Love; My Forged Wedding; Seduced In The Sleepless City; In Your Arms Tonight; Be My Princess; Love Letter From Thief X; My Sweet Bodyguard; A Knights Devotion; Office Secrets; Ten Days With My Devil; Kiss Of Revenge; Dreamy Days In West Tokyo; Class Trip Crush; Our Two Bedroom Story; Kissed By The Baddest Bidder