Tear Jerker / Harvest Moon: A Wonderful Life

• Courting and becoming engaged to one potential love interest, only to turn around and marry a different one results in said love interest — and, in Celia's case, Marlin — to drop by the farm and basically call the player character out over their behavior and leave after a "You suck!" speech.
  • Especially bad for Muffy. Another Wonderful Life and the DS games reveal that she tends to have bad luck with guys and was dumped repeatedly, leading to her lines to the player character over this betrayal to sting even worse.
    Muffy: I thought I didn't want to see you again. But I had to go and do something stupid. Coming here... I was serious about you.
• Nina dying in the interval of Chapter 1 and 2. The player has just seen a very adorable cutscene of their character having gotten married, and a toddler to care for now, and then plays the game. There's a new house near Vesta's farm, and talking to Galen only leads to silence and a very sad expression. It's easy for the player to not even realize that Nina has died for a while.
  • It's just seeing the usual gruff and snarky Galen unable to muster up the energy for a conversation when you go to visit him that's truly heart wrenching.
• It's possible to get a Non-Standard Game Over by neglecting your farm sales in the second year, resulting in your spouse leaving you and taking your child, and Takakura calling you out.
• No matter which girl the player chooses to marry, the others will end up miserable. Muffy remains a single waitress and can be seen going to the beach at night, crying about not having found love, having lost her beauty over the years that might attract a man to her, and never having a child. Celia becomes bitter and a man-hater, who seems to give Marlin hell on the farm. And Nami runs out of money and has to leave the valley and return to living with her deadbeat father, but there is a scene where the player can get her to return for the rest of the game. And she spends most of her time drinking herself into a stupor at the bar.
• Watching your child grow into an adult is bittersweet. You won't have much direction over life choices in later chapters, and (s)he will occasionally lash out at you.
• Among the final cutscenes of the game, the player character's wife will talk about how many years have passed and they have both grown old, and how she doesn't feel as glamorous as she did back then. The player character's line is heartwarmingly painful.
  You're still beautiful.
• The ending of the game has the player character die of old age. Given how this thing never happened before, or has happened since, it's quite a shock to players. Especially the first time around. And while Another Wonderful Life and the Special Edition give a post-credit chapter to play, this wasn't the case in the original version. After that ending, the game was done. No Playable Epilogue or anything.

---