The Most Entertaining Dating Sims, Ranked

Sometimes you seek out a video game to escape from real life and explore a fantasy world that you could never experience in reality. Sometimes people choose to play games that are so similar to their own lives that they allow players to live out their wildest dreams in the most realistic setting possible.




10 Best Dating Sims That Are Available For Free

There is a wide variety of free dating sims you can try without worrying about stressing your wallet!

The latter type comes to life in the form of the simulation genre of games. These titles mimic a version of real life which allows its players to live out their dizziest daydreams. One of the most popular sub-genres in the simulation world is the dating simulation. Here are the best ones available.

Updated on December 24, 2023, by William Quick: Dating can be an awkward, stressful, and embarrassing experience that’s not for everybody. Video games provide an alternative by turning such an experience into a series of fun, comical, weird, unexpected, wild, and more, experiences that you can enjoy from the comfort of your home.

Some of them are worth playing just to see what kinds of things people can come up with and why you would want to date certain beings. Here are some of the most entertaining titles to try.

24 Sucker For Love

Find Love With A Dark God

Sucker For Love Title Art Showing Cthulhu

When Lovecraft was plotting out the content that would form the Cthulhu Mythos, it’s doubtful that romance was one of his primary concerns. That’s why strange game designers have to swoop in with surprising experiences like Sucker For Love.

You play as some sort of shut-in who has developed an interest in the occult. Desperate for a relationship, you resolve to spend all your money on a bunch of accessories, tools, and texts which end up summoning Cthulhu in a feminine form. Since you’re willing to put all reality at risk for love, you may as well enjoy the ride and humor the curvaceous cosmic horror.

23 Boyfriend Dungeon

Date And Dungeon Crawl With Transforming Weapons

Boyfriend Dungeon Art Showing Three Partners Wielding Weapons

If the dating sim genre has proven anything, it’s that you can date absolutely anything if you put your mind to it. Another piece of evidence for this point is Boyfriend Dungeon, which lets you date a variety of fantasy weapons.

Well, to be fair, you’re able to date humans that have the unusual ability to turn into weapons. As the new single person in town, you decide to explore the nearby dungeon that has tailored dangers to your mental state. While there, you find weapons that quickly take on the form of attractive people. Outside the dungeon, you can bond and date to strengthen your relationship, so you can become a stronger team in the dungeon.

22 Hooked On You

Relax And Unwind On An Island With Killers

Hooked On You Title Art Showing The Trapper

Dead By Daylight is a fun multiplayer slasher-inspired game about Survivors trying to escape a menagerie of psychotic Killers. Someone looked at a few of these psychopaths, gave them a makeover, and created Hooked On You.


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You’ve been washed up on a mysterious island where things aren’t what they seem, but thankfully, there’s a resort where you’re a welcome guest. It’s just that the other guests happen to be Dead By Daylight Killers who have let their hair down and want to unwind. You’ll get a chance to talk and connect with all of them before deciding which will be your killer match.

21 Speed Dating For Ghosts

Find New Relationships In The Afterlife

Speed Dating For Ghosts Title Art Showing Two Ghosts

Forming relationships is one of the most significant and time-consuming activities in life. Someone thought that this might carry on into the next life and that’s why we’ve got the Speed Dating For Ghosts event.

Welcome to the afterlife where you’re a ghost and you’re a lonely ghost. That’s why you’ve decided to check out a speed-dating event for other ghosts looking to meet new ghosts. Whether you’re looking for romance, friendship, or just pleasant conversation, each ghost has something going on, and you might help them realize things about life and death in the short time you’ll have together.

20 Love Language Japanese

Fall In Love And Learn A Language

Love Language Japanese gameplay

Ever wanted to learn Japanese and fall in love at the same time? Well, Love Language Japanese is the perfect way to combine those two elements. As many would expect, this dating sim is set in a school for young adults where you meet girls to make friends with or date while learning Japanese.

It’s an adorable if slightly erotic simulator where you get to feel like a real student in Japan who learns and hangs out with friends during the week. Nevertheless, this game is entertaining and educational yet still brings all the elements you know and love from the best dating sim games.

19 Crush Crush

Take Time To Meet And Date A Colorful Cast

Crush Crush gameplay

Crush Crush takes all the typical elements from a traditional dating simulator and adds an idle genre to it. You get to flirt, text, buy gifts, and take anime-style girls out on dates. However, it doesn’t take itself too seriously, and you will end up going out on dates with cat-girls and actual bears.

That being said, this is a great game that will keep you wanting more throughout and fits well for anyone who’s a fan of both the dating sim genre and the idle genre. Click to your heart’s content as you take on more jobs and interesting hobbies to impress the girls you meet along the way.

18 Helltaker

Brave The Depths Of Hell For A Demon Harem

Helltaker Modeus character

Where Crush Crush combines idle clickers with dating sims, Helltaker does a similar thing with puzzle adventures and dating girls from hell. It’s a relatively short game, so you won’t be romancing any girls from hell for too long, but it has great replayability and is free to enjoy.


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It’s the dating simulator where you end up dating demons and have to complete puzzles to try and stop them from killing you and falling in love with you instead. It’s the kind of experience that doesn’t take itself too seriously yet is still fantastically entertaining.

17 I Love You, Colonel Sanders! A Finger-Lickin’ Good Dating Simulator

Learn The Secret Recipe Of Chicken And Love

I Love You, Colonel Sanders! A Finger-Lickin' Good Dating Simulator

For the most part, many will play a dating simulator to get a taste of real life, which is mixed with a touch of ridiculousness and a hint of hidden desires. It’s the perfect recipe for an effective dating sim.

So, if one of those hidden desires is to date Colonel Sanders, then this is the sim for you. It’s simply a game in which you romance someone who looks a little different from how many will imagine him. It’s a classic dating sim mixed with fantastic artwork and a story that will keep you laughing and engrossed throughout.

16 Purrfect Date

Cats Waiting To Say, “Ask Me-owt”

Purrfect Date

Most of the time, you look for a dating simulator with well-drawn, relatively attractive characters and a decent story to keep you playing. This has some well-drawn characters and a story that doesn’t take itself too seriously, but this time it’s combined with sometimes adorable cats.

This is any cat lover’s dream. It’s a game where you get to make choices and take cats out on dates to get them to fall in love with you. It’s a classic love story between an animal and a human that is wrong in so many ways that it makes the game hilariously entertaining to play.

15 Obey Me!

Develop Bonds With Demon Students

obey me - leviathan talking

Obey Me! is a mobile dating sim that’s a cross between a visual novel and a card-based RPG. After a strange dream where a mysterious voice asks you to save them, you suddenly find yourself an exchange student at an all-demon school.


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There, to develop a better understanding between humans and demons, you’re sent to live with seven demon brothers, with whom you have to form pacts to be able to command them. The game has a lot of different paid “gacha”-like events to win cards that unlock outfits and stories for the different characters.

14 The Arcana

Fate And Love Lie In The Cards

the arcana - purple haired woman at a piano

The Arcana is a mobile dating sim created by Nyx Hydra. Mixing the usual elements of dating sims with a mystery and the magic of Tarot cards makes The Arcana a one-of-a-kind dating sim. You can romance six characters and journey through the story in 22 “books” that all relate to Major Arcana on a standard Tarot deck.

You can earn either the Upright End or the Reverse, depending on which choices you make.All routes and endings are free to play with the option to pay for extra content, like CGs and side stories.

13 Amnesia: Memories

Travel To Other Universes To Remember Connections

amnesia memories - talking to orion

Amnesia: Memories is a visual novel game (which means that it occurs in chapters and follows a strict plot that you cannot deviate from). In this game, each choice leads to a new parallel universe in which the heroine pursues a single male character.

The end goal is to regain the heroine’s memories through these interactions and figure out who she was and where she belonged before she lost her memories while becoming acquainted with the selected gentlemen.

12 Akash: Path Of The Five

A Literal Coming-Of-Age Story About Possible Relationships

akash path of the five - talking

Akash is a beautiful visual novel where you take on the role of Aurora. Aurora is an elemental within a village of other elementals and is the first female one within 200 years of the village’s history. This puts a lot of pressure on Aurora with her upcoming coming-of-age ceremony, as well as the tensions between her village and a human settlement nearby.


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11 Katawa Shouju

Go To School And Get Acquainted With Your Fellow Students

Katawa Shouju - main characters

Katawa Shouju is a dating sim that follows the hero’s recovery from a lengthy hospital stay as he transitions into a new school filled with students with a range of different abilities. While adjusting to his new life, the hero also can pursue a romantic relationship with some of his new peers.

However, it is important to note thatthe outcome of these interactions is very dependent on the success of the hero’s attempts to woo his peers, and sometimes the game could end with him just as single as he was at the start of the game.

10 LoveChoice

A Short And Cute Story Of New Love

LoveChoice - character sitting on couch

LoveChoice is a brief dating sim (only around 2 hours long) but that doesn’t have any less impact. LoveChoice is drawn in a very simplistic way, reminding you of the childlike whimsy and the ease of new love.

As the title suggests,this game is all about the choices that people make in their romantic relationships – every scene matters. As a result, it also has some replayability value, extending the 2-hour playtime by a bit.

9 True Love

Fight To Have A Social Life Among Schoolwork

true love - player is offered food

True Love is one of the original dating simulation games. Though it was released in Japan in 1995, it did not receive a North American release until 1999. You can experience the story from the perspective of a high school boy who is finding his coursework far more difficult than expected, as well as trying to juggle maintaining an active social life.


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The game occurs within a set time frame and is molded by player choice. The game also has high levels of replayability, as you can simply follow a new path and receive a unique experience.

8 Riddle Joker

Be A Secret Agent In A School Of Magical People

riddle joker - ayase with a muffin

In Riddle Joker, you play Arihara Satoru, a seemingly ordinary guy who’s a secret agent. In the game world, magical abilities have been proven real when scientists discovered a special particle, called the “Astron.”

The company you work for uses people who can control Astrons. You’re sent to attend a famous academy that teaches these magical people,known as “Astrals” – but you’re found out! Turns out, the students have secrets of their own.

7 Monster Prom

Try To Get A Date With A Monster For The Dance

monster prom - cover of teen wolf magazine

Monster Prom is a sweet, quirky, and fun dating simulator that allows you to play as one of several monsters as they navigate the uneasy waters of high school.

You’ll have numerous chances to boost certain stats to woo different monsters (as each monster has a preferred personality for potential partners) in time for the prom (which comes at the end of the game).

The majority of the gameplay is centered around helping your monster peers with their problems. High school is never easy for anyone.

6 Max Gentlemen Sexy Business

Rise Up In Business And In Love

max gentlemen sexy business! - talking to battle butler

For Dating Sim fans who want humor and shenanigans with their romance, Max Gentlemen Sexy Business! is the game for you. It’s part Dating Sim, part Business Tycoon, as all of your romantic options are also other business executives who will help you return your family business to its former glory.

Based in Victorian-era London,you can customize not only your “Gentsona”, but you can also unlock outfits and items to customize your executives. The game also allows you to control what content you want to see with a spoiler tag system and character-specific settings.

5 Doki Doki Literature Club

Get Involved In An Innocent Club With Seemingly Innocent Members

all of the girls from Doki Doki Literature Club taking a selfie. Pictured is Yuri, Natsuki, Monika, and Sayori

The best dating sims are the ones that go against convention and surprise you. Doki Doki Literature Club is a dating sim that rose in popularity due to the intense twist that occurs halfway through the game.


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Though the game appears to be a typical cutesy and rose-colored dating sim, it slowly devolves into an intense and brutal psychological horror. This twist led to a surge in popularity in streaming communities as people wanted to see their favorite creators react to each element of the game from start to finish.

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