Anyone who enjoys whirlwind romances, charming and mysterious love interests, or even just illustrations of characters that are attractive and pleasing to the eye understand the allure of dating sim games. Whether people are in it for the art, the characters’ stories, or an escape from their own love lives, there’s no denying that dating games have earned a solid place in many players’ hearts.
However, along with the smiles and happy endings, there’s no shortage of tensions, broken hearts, and bad endings across the genre that can leave many players feeling betrayed or even punished for the choices they’ve made. While working for a happy ending is a common feature of the genre, some games take this a step further by punishing certain character choices entirely, intentionally or otherwise.
10 Love Island: Ex In The Villa
Inspired by the hit reality tv show Love Island, Love Island: Ex in the Villa is the fifth and latest installment of a series from Fusebox Games that aims to give players the experience of a Love Island contestant. In the latest season, Love Island: The Game takes on a different approach from previous seasons by bringing in a story that’s far more focused on the main character, as their ex is revealed to be another contestant on the season.
Unfortunately, this story comes with far more linear expectations of what the player wants, and should the player try to pursue anyone other than their ex, they’ll soon find out how much the story will punish them for deviating from that narrative.
9 Dream Daddy: A Dad Dating Simulator
Anyone who was a part of the dating game scene (and even people who weren’t) likely remember when this game came out, and for good reason. Offering a new and refreshing approach to the typical dating game formula – assuming the role of a single dad romancing other neighborhood dads – along with a colorful cast of charming and eclectic fathers and their families.
Among all the hot, single dads, Joseph stands out as the only married man on the culdesac. In addition to an infamous, far darker ending players could discover on his route, the inability to be Joseph’s first choice lead to many players feeling cheated and underwhelmed if they pursued him.
8 Hatoful Boyfriend
A game centered around being the only human in a school full of pigeons, Hatoful Boyfriend is a dating game that’s as strange as it is unforgiving. Considering every love interest in the game is a pigeon, it comes as no surprise that Hatoful Boyfriend doesn’t take itself too seriously, and many choices can have unexpected and often chaotic results, for better or (more frequently) for worse. In fact, players will find it is incredibly easy to take a wrong turn and fall victim to a terrible fate, whether it’s from failing to romance someone, or romancing the wrong person.
7 Sucker For Love: First Date
Blending romantic dating sims with eldritch horror, Sucker For Love: First Date takes players on the precarious tightrope walk of dating an eldritch deity without losing their sanity before the end of the world. This is especially true in the second part of the game, where players are caught in a love triangle between two deities.
Players who aren’t sure what they’ll want, or wish to pursue both characters at once should do so carefully: the wrath of a broken-hearted deity is not to be taken lightly, and trying to perform conflicting rituals will have horrible consequences.
6 Doki Doki Literature Club
Another classic in the intersection between dating and horror games, Doki Doki Literature Club became a quick classic that captured the attention of the internet when its unique approach to the genres first came out. Starting out as an otherwise cute and innocuous dating sim where a guy gets roped into joining a high school literature club, the story quickly takes a turn for the dark and horrifying as the player starts to connect with the characters.
Instead of punishing players for picking one character, Doki Doki Literature Club takes it a step further by punishing players for any character route they pursue to progress the story.
5 Mystic Messenger
Mystic Messenger put a unique spin on the dating game genre when it entered mobile app stores in 2016 as a dating game where all characters interact with the player’s character through the medium of a phone app, including chat rooms, phone calls, and email inboxes.
With a deep and mysterious story unwinding through a unique and immersive medium, players would learn more about the forces behind the story on each route. However, not all character routes are created equal, leading to some routes sacrificing story for romance, and others sacrificing a connection to the character for the overarching story.
4 Asagao Academy: Normal Boots Club
Originating from a successful Kickstarter Campaign, Asagao Academy: Normal Boots Club is a romantic visual novel featuring a group of Youtubers who are part of a group known as the Normal Boots Club, with each Youtuber as a possible love interest for players and fans to pursue.
For the most part, the game is a fun and evenly distributed experience of romance and laughs, however players should keep in mind that certain characters’ routes can harm their relationship with others if they choose to pursue them.
3 Vampire Knight DS
Based on a popular manga and anime by the same name, Vampire Knight DS was an otome game previously available only in Japanese, until an unofficial English translation came out in recent years. Stepping into the shoes of Yuki Cross, players can romance six different vampires from the series at Cross Academy, plus a seventh, secret love interest.
While there are plenty of enjoyable dark romances the vampire genre is well known for, not all characters are created equal and not all routes end with a happy couple. In fact in some cases, the love endings for certain characters have received complaints for having very little love in them at all.
2 Nightshade
Taking place in Japan during the Sengoku period, Nightshade follows two opposing ninja clans as they enter a period of tentative peace and one ninja in particular as she graduates from her training and leaves for her first mission only to get tangled in conspiracy.
With five different love interests and an interesting story with gorgeous graphics and music, players have a lot to enjoy while pursuing romance in Nightshade. That being said, the balance between romance and angst is far from evenly distributed, and some players have remarked that certain characters’ screentime suffers as a result, even on their own routes.
1 Dairoku: Agents Of Sakuratani
Dairoku: Agents of Sakuratani blends supernatural elements with a slice of life story as players romance a cast of characters in a story heavily inspired by Japanese myths and folklore. Instead of focusing on drama or intrigue, Dairoku: Agents of Sakuratani instead emphasizes easy gameplay and forming bonds with characters in a wholesome, low pressure setting; unless characters are in a lost or broken love ending, the storyline is safe with little prolonged conflict. Unfortunately, the romance of certain characters was disappointing, stilted, or felt unnatural and impossible to pursue, making their romantic routes suffer.