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- Any time Nancy gets a Game Over sequence that results in death or injury is depressing in hindsight. Just thinking about Nancy's family and friends mourning her loss is enough to make you glad that Second Chance is a thing.
- The culprits. While their actions in-game are despicable, it's sad to see how it happens: ordinary people allow their emotions - be they anger, jealousy, desperation, and whatnot - to get the better of them, which in turn, drives them to do horrible things. Made even worse if they were your friend first.
- On a meta level, the delayed release of Midnight in Salem. Because of Her Interactive's decision to move to a new gaming system (and reportedly, internal trouble within the company itself), the game's release continues to get pushed back. As a result, both the company and the fans have experienced a four-year hiatus in which no new games have come out. Considering how Her Interactive used to release a minimum of two games per year, it's sad for fans who miss their favorite sassy detective.
Secrets Can Kill
- The death of Jake Rogers can be considered this. Even though he was widely regarded as a jerk whom nobody liked, the fact that he was killed at such a young age is rather pitiable. If nothing else, his parents are probably upset.
Stay Tuned for Danger
Message in a Haunted Mansion
Treasure in the Royal Tower
The Final Scene
- Joseph. The theater he's looked after and loved for so long is being demolished, and there's nothing he can do about it. His original plan afterwards was to move out to Arizona to be with his brother, until he gets a letter from a lawyer revealing that his brother has died. This makes his motives behind kidnapping Maya more understandable because he was desperate to save the place that had essentially become his home. In addition, he was so nice to Maya during her captivity that she is even willing to testify on his behalf.
Secret of the Scarlet Hand
- A bit of a Fridge Tear Jerker, but the Game Over sequence where Nancy suffocates to death in the monolith and her body isn't found until 700 years into the future. Even thinking about such a horrible fate for our favorite detective - dying all alone in a darkened room with only a rotten corpse for company - is enough to make anybody sad. The fact that her friends and family would never know what happened to her either is just beyond heartbreaking.
Ghost Dogs of Moon Lake
- William Akers' journal entries about how badly-off his family ended up after Mickey Malone's arrest are pretty heartwrenching to read.
The Haunted Carousel
- In the game, the side plot involves the late Daryl Trent's attempt to bring happiness to his repressed daughter, Joy, using a homemade robot called ''Miles the Magnificent Memory Machine." Throughout the game, Miles helps to purge Joy's anger against her late mother and remember how much she loved Captain's Cove theme park, and specifically, the carousel. The entire process is painful to watch, especially as Joy expresses regret for actions she can't even remember. However, this culminates in the discovery of a carousel horse Joy's mother bought for her as a child, along with the last remaining photo of her mother and a letter from Daryl telling Joy how much they both loved her.
- The historical backstory is pretty sad as well. Rolfe Kessler, the titular carousel's creator, was in love with and married a woman named Amelia, but his personality was so intense and moody that she could not live with him, although she loved him in return. As a result, they separated and he wrote letters to her, but never sent them. Eventually they reunited, only for her to die of tuberculosis shortly afterwards.
Danger on Deception Island
The Secret of Shadow Ranch
- The historical backstory for this game is just downright depressing: Frances, the sheriff's daughter, falls in love with the outlaw Dirk, and they begin a romance. When the sheriff finds out, Dirk is hanged, and Frances leaves Arizona forever without knowing about his final letters. In the end, the sheriff dies all alone, full of regret for driving away his beloved daughter. In fact, the paper his final diary entry was written on has stains left behind by his tears.
Curse of Blackmoor Manor
- There's a bit of a Fridge Tear Jerker when you recall how Jane's father talked about his father, and you realize that for roughly seven hundred years, the hidden rituals practiced by every other generation of the Penvellyn family have been causing its members to remain distant from their parents and children. All for a rock.
- Jane. Even though she appears content with both her studies and her hobbies, in reality, she is terribly lonely and bored most of the time. Case in point: The reason she's so happy to have Nancy around is because she finally has someone else to play with. Even her motive as the culprit can be pitied in some way, for the reason she tricked Linda in the first place was because she wanted her father and mother to get back together.
Secret of the Old Clock
- Emily. She's only seventeen years old, but she's just lost her mother and will be responsible for running the inn as well once she turns eighteen in a few months. She has one of her mother's old friends to help her out until then, but she's not sure if she can last that long due to the inn's money troubles and her own deteriorating mental health. Things get slightly better for her in the end when she realizes Jane/Marion was responsible for making her think she was losing it, but considering the game takes place during the Great Depression, she still has a long road ahead of her.
Last Train to Blue Moon Canyon
- Another game with a tragic historical plot. The train's owner, Jake Hurley, was a rich man who wandered through the Old West in search of gold - until he met the beautiful Frenchwoman, Camille Voulet. After they married, he commissioned a custom train to serve as their home, and they spent their time in happy travels. Then one day, Camille fell and hit her head. She seemed to recover, but then died unexpectedly.
- Not to mention Jake dying alone in the depths of a mine, and his train operator expiring from a heart attack while attempting to drive the train back to town, presumably seeking help because his boss hadn't come back.
Danger by Design
- The entire backstory of Noisette Tornade. She coded messages for the Resistance during World War II, and moonlighted as a French spy translating for the Germans. Out of an intense love for Paris and its art, she employed the help of her German lover, Hans, to steal and hide several pieces of beautiful stained glass so they wouldn't be destroyed during the war. After the war, when her countrymen discovered her liaisons with Germany, they immediately accused her of treason. Although she was acquitted, she remained bitter that the city she loved had turned so suddenly against her. This led her to never reveal the location of the stained glass windows, even during her time as Director of Public Works for the city. To top it all off, Hans went back to Germany and despite promising otherwise, Noisette never saw him again.
- The love triangle that exists between Minette, Dieter, and Heather (albeit unknowingly). To sum it up, Minette and Dieter dated until she broke it off, but he's still in love with her and unaware of Heather's feelings towards him. It's a sad situation all around.
The Creature of Kapu Cave
- Mike and Pua's reasoning for destroying the pineapple crops and blaming it on the Hilihili's research facility. As it turns out, Mike owes quite a bit of money to a local loan shark, and since he would be the first to inherit the Hilihili if it went out of business, he and Pua saw this as a way out of their dilemma. Not exactly an ethical plan, but knowing how desperate they were to find a solution makes their actions somewhat easier to understand.
- In addition to that, now that they've been arrested, how are they going to pay off their remaining debt?
The White Wolf of Icicle Creek
Legend of the Crystal Skull
- Henry Bolet. Think about it: his parents die in a car crash when he was eight, and having no other family, he's sent to live with a great-uncle who had no idea how to raise a little boy. This resulted in him shipping the young Henry off to boarding school, summer camp, military school, and college, leaving Henry to grow up feeling alone and unloved. This resulted in Henry having few friends and a horrible girlfriend as a result of a his inability to connect with other people. Gets slightly better at the end of the game when he discovers how much Bruno actually cared for him, and not just financially either.
The Phantom of Venice
The Haunting of Castle Malloy
- Kit. The ex he's still in love with is getting married to his best friend. That's got to be hard.
- Everything that happened to Fiona. After her parents were killed in the explosion, she was taken in by a hermit who lived on the edge of the bog. Growing up with little to no social contact impacted her mental and emotional development, and as a result, she had no idea how to interact with humans. Thankfully, after the police take her into custody and place her in a care home, she improves dramatically.
Ransom of the Seven Ships
- Watching George fall apart after Bess's kidnapping can be hard to watch, especially when she begins to display shades of It's All My Fault behavior. Considering how Bess is both her cousin and one of her best friends, it's easy to see why she's so upset.
Warnings at Waverly Academy
- Rachel's backstory. She's actually identical twins who, after their mother died, both pretended to be one person so they wouldn't lose their scholarship and potentially wind up in a foster home.
- The drama involving Izzy and Leela. To put it bluntly, Leela's boyfriend asked Izzy to an upcoming dance, and she accepted. That's enough to make anybody feel like garbage, and the fact that Izzy feels no remorse for it makes it even worse. Made slightly better by the fact that Leela appears to bounce back afterwards, but it's still a crummy thing to go through.
- Mel's reaction to being accused of plagiarism. When asking Nancy to help prove her innocence, she outright acknowledges how unpopular she is. Her statement on the matter is heartbreaking:
"Becca, look. I'm not anyone's favorite person at this school. The kids, the teachers - if I get kicked out, nobody's gonna care. But I don't deserve this, and I need help."
Trail of the Twister
Shadow at the Water's Edge
- Kasumi's death and how much everyone blames themselves for what happened. To clarify, she was supposed to go into the city that day to meet her American pen pal, but Takae pretended to be sick so she couldn't go. As a result, Kasumi wound up having to clean the older of the two bathrooms at the Ryokan, but because she didn't have as much experience as Takae, slipped and fell into the water. It's implied she hit her head as well, because she drowned and Yumi was the one who found her unconscious body. The reason that Takae, Yumi, and Miwako blame themselves so much is because they were all home at the time of her death, but did not realize what happened to her until it was much too late.
- Doubly so in Takae's case, when you consider the fact that her actions indirectly resulted in Kasumi's death. She faked her illness because she didn't want Kasumi getting ideas about leaving the Ryokan - and she never did.
- Miwako. On the outside, she acts like everything is fine for the guests, but it's clear that the troubles with the Ryokan are starting to get to her.
The Captive Curse
Alibi in Ashes
- Reading Alexei's old case diary. Watching what begins as a somewhat goofy and cheerful record of his cases suddenly switch to him detailing his downfall and how no one trusts him anymore is absolutely heartbreaking, particularly as he states he's writing in it again to try and find comfort in the youthful spirit he once had in his sleuthing.
- Watching the entire town of River Heights turn against Nancy for a crime she didn't commit. After all those years of doing favors for the townspeople, one false accusation is enough to make none of that matter.
Tomb of the Lost Queen
The Deadly Device
- Niko's murder. All he wanted to do was use his skills to make life easier for people, and someone killed him for it. He also has the heartbreaking honor of being the first murder victim in the game series since Secrets Can Kill.
Ghost of Thornton Hall
- The overriding atmosphere of the game isn't just fear - it's sadness. You never even meet Charlotte, but her death influences everything and everyone at Thornton Hall.
- The ending where Nancy chooses not to save anyone. You find out in her letter to Ned afterwards that as a direct result of her actions, Jessalyn and Harper have been hospitalized, Wade and Colton aren't returning her calls, and Clara still hasn't been found. She then admits she doesn't know what to say this time and wishes she could go back and do things differently. The regret she displays is utterly heartbreaking, especially when the actions that lead her there are so out of character for someone like Nancy. Thankfully you have two other endings to choose from so it doesn't have to be this way, but it's still sad.
- In relation to that, the ending where you choose to save Jessalyn and Harper, but not Clara. In this ending, the players find out that while the former two made it out okay, again, Clara still hasn't been found. Because of that, Jessalyn decides to take some space from the family, possibly permanently, and Wade has done the same. Even the letters Savannah wrote to try to reach him are simply returned to her unopened. In this version, there's also the added bonus of a girl telling Nancy she saw the figures of two women floating in the smoke above the island, implying that Clara did in fact perish in the fire. Even Nancy, who outright said she doesn't believe in ghosts, admits to feeling creeped out.
The Silent Spy
- The argument between Carson and Kate in one of the flashbacks is particularly heart-wrenching when you know it's very likely the last conversation they ever had before Kate's death.
- Nancy's letter at the end to her mother.
- Not to mention the letter from her mother to her.
- One of the flashbacks with Nancy and Kate. When Nancy asks if her mother will come back from Glasgow, Kate says that she's not sure and that she knows how unfair it is to not know. She may have been aware that going to Scotland was a one-way trip, but she felt inclined to go because she wanted to stop Revenant. By doing so, she knew she would be leaving her family behind and miss out on Nancy growing up, but she did it anyways because she wanted to keep the world - and by extension, Nancy - safe from harm. That's a hard decision to make for any parent.
The Shattered Medallion
Labyrinth of Lies
Sea of Darkness
- This game has a massive one: Gunnar wound up losing everything when his wife and child died in a boat accident, so he's become a grumpy old man whose only possessions are literally the clothes and box he holds. It then turns out that his daughter looks like Nancy. You WILL need tissues here.
- The whole backstory of the Captain of the Heerlijkheid.
- On a meta level, the fact that this is the last installment of the series to feature Lani Minella as Nancy Drew's voice actress. Considering she had been with the games ever since the first installment, a number of fans - many of whom had grown up hearing her voice - were heartbroken to hear the news, and considered it to be the end of an era. It didn't help that rumors surrounding her dismissal imply that it wasn't willing on her part.
- Nancy and Ned's breakup in "Two Points To Murder", book #8 of the "Files". It's quite wrenching in the first place, even more so if you've been reading the books since their first inception and all but grown up with this love story. Fortunately, they reconcile a few books later, but it's still hard to take.