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Games Like A Date With Chester 2

60+ similar titles based on shared tags and player behavior. Themes include Visual Novel, Dating Sim, Romance, Singleplayer.

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  1. #1 PockeDate! - Pocket Dating Simulator
    97% matchOverwhelmingly Positive97% of 2,324 reviews2024
    Dev: TERNOX
    Windows

    Your Pocket-Sized Dating Simulator! Every launch brings a new date with unique dialogues! Spend endless hours with your adorable, love-struck virtual girlfriend.

    Why similar: Dating Sim 36.9%, Visual Novel 22.6%, Romance 20.5%, Multiple Endings 8.2%, Horror 6.1%

  2. #2 Date Everything!
    96% matchVery Positive94% of 6,867 reviews2025
    Dev: Sassy Chap GamesPub: Team17
    Windows
    Median: 5.1 hrsMean: 11.2 hrs≥1hr: 82%

    Date Everything! is a sandbox dating simulator set in the comfort of your own home, featuring 100 fully voice acted datable characters! Let the romance flow between your bed, smoke alarm and… Overwhelming Sense of Existential Dread? Are you ready to Date Everything?

    Why similar: Dating Sim 38.1%, Romance 22.8%, LGBTQ+ 16.6%, Visual Novel 10.9%, Multiple Endings 8.7%

  3. #3 Find Love or Die Trying: Til Death Do Us Part
    96% matchMixed69% of 162 reviews2025
    Dev: Sunseeker Games
    Windows · Linux

    The afterstory to Find Love or Die Trying is here! Continue your romance with your chosen partner in the world beyond the killer dating show. Will your love survive, when the world turns against you?

    Why similar: Dating Sim 41.1%, Romance 25%, Visual Novel 21%, Multiple Endings 8.8%, 2D 2.2%

  4. #4 A Date with Death
    95% matchOverwhelmingly Positive98% of 13,259 reviews2023
    Dev: Two and a Half Studios
    Windows · Mac · Linux
    Median: 3.0 hrsMean: 7.9 hrs≥1hr: 72%

    Fight against & romance the one hunting for your soul in A Date with Death, a romance chat simulator where you date(?) the Grim Reaper himself. Create your own character, decorate your apartment, and chat away with the charming yet dangerous Grim Reaper through text and video calls.

    Why similar: Dating Sim 44.1%, Romance 19.8%, Visual Novel 18.1%, LGBTQ+ 12.7%, Multiple Endings 5.3%

  5. #5 Monster Prom 2: Monster Camp
    94% matchOverwhelmingly Positive96% of 6,101 reviews2020
    Dev: Beautiful Glitch
    Windows · Mac · Linux
    Median: 5.0 hrsMean: 8.8 hrs≥1hr: 89%

    "Monster Prom 2: Monster Camp" brings you more of the world's best (and maybe only?) multiplayer dating sim; but in a way you've never expected!

    Why similar: Dating Sim 35.6%, Romance 17.7%, Visual Novel 15.6%, LGBTQ+ 13.6%, Multiple Endings 11.1%

  6. #6 A Date in the Park
    94% matchVery Positive88% of 1,998 reviews2016
    Dev: Cloak and Dagger Games
    Windows
    Median: 48 minMean: 3.1 hrs≥1hr: 36%

    A short and mysterious free point and click adventure game, inspired by the feeling of oddness in an everyday situation.

    Why similar: Romance 42.6%, Point & Click 18.1%, Horror 11.7%, Exploration 9.1%, Adventure 8.1%

  7. #7 Friendsim 2
    93% matchVery Positive88% of 102 reviews2022
    Dev: Studio June
    Windows · Mac

    In this episodic visual novel, follow the adventures of MSPA Reader as they return to Alternia once more to save their friends... and realize that nothing is as it seems.

    Why similar: Visual Novel 23.9%, Cartoon 16.4%, Aliens 16.4%, Multiple Endings 15.5%, LGBTQ+ 13.7%

  8. #8 My Furry Protogen 2 🐾
    91% matchOverwhelmingly Positive96% of 528 reviews2024
    Dev: Dirty Fox Games
    Windows
    Median: 3.2 hrsMean: 16.1 hrs≥1hr: 84%

    After every night comes a new dawn, filled with hope and light. As the adventure of our heroes continues, let’s discover what lies ahead!

    Why similar: Dating Sim 41.5%, Visual Novel 26.2%, Romance 20.5%, Adventure 8.6%, Singleplayer 3.2%

  9. #9 Bloody Painter Dating Sim
    91% matchVery Positive90% of 1,598 reviews2024
    Dev: DeluCat Productions
    Windows

    You have unfortunately been captured by a serial killer, and you must increase your chances of survival within seven days. Your choices will determine how he treats you and the outcome of your relationship. What will your final relationship with him be...?

    Why similar: Dating Sim 44.6%, Visual Novel 19%, Romance 14.7%, Cartoon 7.4%, Multiple Endings 5.9%

  10. #10 Purrfect Date - Visual Novel/Dating Simulator
    92% matchMixed60% of 470 reviews2017
    Dev: Bae TeamPub: Bossa Studios
    Windows
    Median: 30 minMean: 6.7 hrs≥1hr: 38%

    As Cat Island’s newest arrival, it’s not long before you realise something’s seriously amiss, or should we say… amorous! A blend of mystery, intrigue and wickedly black humour, will you discover your Purrfect Date before it’s too late? Remember, curiosity killed the cat...

    Why similar: Dating Sim 44.4%, Visual Novel 19.8%, Romance 17%, Multiple Endings 9%, Adventure 6.1%

  11. #11 Sucker for Love: First Date
    89% matchOverwhelmingly Positive98% of 2,933 reviews2022
    Dev: AkabakaPub: DreadXP
    Windows
    Median: 2.3 hrsMean: 5.2 hrs≥1hr: 69%

    Put the 'love' in 'Lovecraftian horror'! Perform terrifying rituals to win the affections of eldritch horrors and smooch 'em... at any cost!

    Why similar: Dating Sim 30.2%, Romance 24.6%, Visual Novel 17.1%, Multiple Endings 11.4%, Point & Click 6.3%

  12. #12 My First Femboy Date
    90% matchVery Positive86% of 325 reviews2022
    Dev: owlyboi
    Windows

    You've matched with a cute femboy on an app. The date is set and you meet him at the amusement park.

    Why similar: Visual Novel 31.7%, Romance 28.9%, LGBTQ+ 24.3%, Adventure 7.8%, 2D 5.2%

  13. #13 Two Beasts Or Not To Beast!
    89% matchVery Positive100% of 63 reviews2026
    Dev: TokinokogiriPub: FAKKU
    Windows

    With the day filled with abundant temptations, can you resist the seductresses around you and impress your crush, or will you give in to their flirtations? This furry lovers’ dating sim dream is about to begin!

    Why similar: Dating Sim 35.3%, Romance 26%, Visual Novel 19%, Multiple Endings 8.2%, Adventure 6.4%

  14. #14 A Warmer Shade of Summer
    88% matchMostly Positive76% of 117 reviews2021
    Dev: 52.6 Productions
    Windows

    You return to the family farm to find it in disrepair. Maybe you have what it takes to bring it back to its former glory? Who knows who you'll meet on you're way? An old friend? That special someone? Anything is possible in Summerset.

    Why similar: Dating Sim 41.1%, Visual Novel 28.9%, Romance 26%, Singleplayer 2.4%, Indie 1.6%

  15. #15 a completely normal dating simulation that is definitely completely sweet, innnocent and normal: SOMETHINGETH ANIVERSARY EDITION
    86% matchVery Positive90% of 219 reviews2022
    Dev: Educated Child GamesPub: Educated Child Games but it's a publisher
    Windows · Mac

    a fun dating sim where you get to date stick figures! but... is that all it is? i doubt it. why don't you find out? find out just how much more there is in this game than simply a fun dating sim where you get to date stick figures? spoiler: there is also a baguette

    Why similar: Indie 100%

  16. #16 Superstorm Melon Date
    87% matchVery Positive91% of 74 reviews2021
    Dev: A. Hagen
    Windows · Mac

    It's date night in the dystopian future. You're going out with Mel, a half-melon person with psychic powers. They seem a little weird, but at least they're cute. Choose where to go, what to do, and what to say in this highly interactive, romance visual novel.

    Why similar: Dating Sim 32.9%, Romance 30.2%, Visual Novel 22.5%, Multiple Endings 12.4%, Indie 1.3%

  17. #17 Sucker for Love: Prelude
    86% matchOverwhelmingly Positive97% of 515 reviews2021
    Dev: AkabakaPub: DreadXP
    Windows
    Median: 36 minMean: 12.6 hrs≥1hr: 29%

    Preform a series of scary rituals to win over an eldritch cutie and win a smooch!

    Why similar: Dating Sim 70.3%, Multiple Endings 15.7%, Horror 9.6%, Singleplayer 2.8%, Indie 1.6%

  18. #18 Sucker for Love: Date to Die For
    84% matchVery Positive95% of 1,247 reviews2024
    Dev: AkabakaPub: DreadXP
    Windows
    Median: 4.3 hrsMean: 4.5 hrs≥1hr: 82%

    Put the ‘love’ in 'Lovecraftian horror!' Avoid the fanatical cultists and survive dangerous rituals to escape the Black Woods with your life in this 90’s anime inspired visual novel!

    Why similar: Dating Sim 39.7%, Visual Novel 22.3%, Romance 12%, Point & Click 7.1%, Horror 6.7%

  19. #19 Date Ariane Remastered
    85% matchMostly Positive75% of 62 reviews2022
    Dev: Date Ariane Games
    Windows

    The original western dating sim updated and bigger than ever before. The first dating sim made with 3D rendered graphics became a viral web classic back in 2007. This new "remastered" version allows players to play as a male or female for the first time.

    Why similar: Dating Sim 33%, Romance 22.3%, Visual Novel 19.3%, LGBTQ+ 8.3%, Point & Click 7%

  20. #20 From Madness with Love
    83% matchVery Positive91% of 496 reviews2023
    Dev: JamsanpoidPub: VampireK.K.
    Windows

    This is a dating sim with guys you will never be on the same page with! For some reason, you just can't communicate with the guy you like... An unusual yet extraordinary experience with a cute pixel art style, fully voiced in Japanese.

    Why similar: Visual Novel 28%, Romance 25.1%, Multiple Endings 14.9%, LGBTQ+ 14.5%, Dating Sim 8.6%

  21. #21 Arcade Spirits: The New Challengers
    84% matchVery Positive89% of 186 reviews2022
    Dev: Fiction Factory GamesPub: PQube
    Windows · Mac · Linux
    Median: 3.3 hrsMean: 6.4 hrs≥1hr: 93%

    Arcade Spirits: The New Challengers is the follow-up to 2019's Arcade Spirits, a visual novel of love and pixels, in which you seek friendship and romance while working in an arcade. Now the tables are turned, as you seek friendship and romance while PLAYING in an arcade!

    Why similar: Dating Sim 29.2%, Romance 23.6%, Visual Novel 20.8%, LGBTQ+ 14.5%, Adventure 6.1%

  22. #22 Courtin' Cowboys
    82% matchVery Positive95% of 62 reviews2024
    Dev: Mrfishess
    Windows · Mac · Linux

    It's 1863 and you, the player, are traveling through the small western town of Summerfair. Meet up to 7 love interests and discover their deliciously dark pasts... as well as their current horrifying misdeeds.

    Why similar: Dating Sim 31.2%, Cartoon 19.3%, Visual Novel 17.8%, Romance 10.1%, LGBTQ+ 7.8%

  23. #23 Find Love or Die Trying
    80% matchOverwhelmingly Positive97% of 12,005 reviews2021
    Dev: Sunseeker Games
    Windows · Mac · Linux
    Median: 1.6 hrsMean: 19.6 hrs≥1hr: 59%

    Welcome to the only killer dating show where ending up single means ending up dead! Date or die, it's up to your choices!

    Why similar: Dating Sim 41.5%, Romance 24.2%, Visual Novel 21.1%, Multiple Endings 9%, 2D 1.9%

  24. #24 Tender: Creature Comforts
    82% matchVery Positive90% of 106 reviews2021
    Dev: Kenny Sun
    Windows · Mac

    Tender is a narrative game that explores connection and rejection in the era of swipe culture. It’s a story told by and through the modern interface for finding love.

    Why similar: Dating Sim 30.6%, Cartoon 17.8%, Visual Novel 16.3%, Romance 11.1%, Aliens 10.4%

  25. #25 Coming Out on Top
    81% matchOverwhelmingly Positive96% of 1,392 reviews2017
    Dev: Obscurasoft
    Windows · Mac · Linux
    Median: 4.4 hrsMean: 13.1 hrs≥1hr: 82%

    The acclaimed gay dating sim. Have a sweet, sexy, or bizarrely comedic adventure with the man of your choice!

    Why similar: LGBTQ+ 39.7%, Dating Sim 30.9%, Romance 12%, Visual Novel 11.1%, Multiple Endings 5%

  26. #26 Yuri Dating Agency
    81% matchVery Positive89% of 99 reviews2023
    Dev: Red bean Taiyaki
    Windows · Mac

    Yuri Dating Agency - a speed dating simulator for WLW. You're a girl who likes girls, walking into this Yuri dating agency to find yourself a date. Here, you will be able to get to know lots of girls. Will you be able to win their hearts?

    Why similar: Visual Novel 27.2%, Dating Sim 27.2%, LGBTQ+ 23.8%, Multiple Endings 14.6%, Horror 7.2%

  27. #27 Bliss Valley
    79% matchVery Positive98% of 54 reviews2025
    Dev: Amusement Studios
    Windows · Mac · Linux

    While running errands, you'll meet three cute furry characters that you can potentially date, romance, and eventually seduce. This game contains explicit sexual content.

    Why similar: Visual Novel 37.5%, Romance 25%, LGBTQ+ 17.9%, Multiple Endings 9.1%, 2D 7%

  28. #28 Fetish Locator Week Two
    78% matchVery Positive87% of 1,858 reviews2021
    Dev: ViNovella Games
    Windows · Mac · Linux
    Median: 4.2 hrsMean: 10.4 hrs≥1hr: 84%

    The second installment of the Fetish Locator Trilogy is here! Find out what's next for our protagonist as he's thrown into a lewd frenzy with over 20 girls! How will your prior choices ultimately affect things? Test your limits as you seduce and romance your way to the top in Fetish Locator!

    Why similar: Dating Sim 32.8%, Visual Novel 26.7%, Romance 18.5%, LGBTQ+ 12.5%, 3D 7.2%

  29. #29 Lust Academy - Season 2
    78% matchVery Positive83% of 692 reviews2023
    Dev: Bear in the Night
    Windows · Mac · Linux
    Median: 6.5 hrsMean: 26.1 hrs≥1hr: 89%

    Continue your adventure in Cordale Academy, following up on your previous choices and experiencing all-new content, including: Story, Animations, Locations, Quests and more!

    Why similar: Dating Sim 25.2%, Romance 22.9%, Visual Novel 21.2%, LGBTQ+ 13.8%, Multiple Endings 10.6%

  30. #30 Friendship with Benefits 2
    76% matchVery Positive94% of 186 reviews2025
    Dev: TwistedScarlett60
    Windows · Mac · Linux

    Arcadia has changed, but its gorgeous ponies haven’t. In this eroge, explore a new world, unlock over 40+ explicit scenes, and romance 25+ unique girls, all eager to share their deepest desires with you. Where will you begin in this new world?

    Why similar: Dating Sim 59%, Visual Novel 34.6%, 2D 5.8%, Singleplayer 0.6%

  31. #31 Lunar's Chosen - Episode 2
    77% matchMostly Positive76% of 76 reviews2024
    Dev: PTGames
    Windows · Mac · Linux

    Lunar's chosen introduced a world of magic, danger, romance and sex. With a whole host of changes and improvements, animations and HD renders, the story continues in Lunar's Chosen Episode 2!

    Why similar: Dating Sim 32.8%, Romance 25.3%, Visual Novel 18.8%, LGBTQ+ 12.1%, Hidden Object 7.4%

  32. #32 Emily is Away Too
    77% matchVery Positive93% of 6,144 reviews2017
    Dev: Kyle Seeley
    Windows · Mac · Linux
    Median: 3.2 hrsMean: 15.1 hrs≥1hr: 85%

    Emily is Away Too is a brand new story featuring new characters and multiple different endings. Message your friends, surf the web and choose your path through this branching narrative.

    Why similar: Dating Sim 47%, Visual Novel 18.7%, Multiple Endings 15.5%, Romance 7.8%, Adventure 4.2%

  33. #33 Blossoms Bloom Brightest
    79% matchMixed70% of 207 reviews2017
    Dev: Reine Works
    Windows · Mac · Linux
    Median: 18 minMean: 8.0 hrs≥1hr: 26%

    A sci-fi, yuri visual novel with a dollop of mystery.

    Why similar: Romance 23.1%, Visual Novel 19.9%, Dating Sim 17.8%, LGBTQ+ 14.4%, Multiple Endings 7.4%

  34. #34 Lovers of Aether
    76% matchVery Positive94% of 1,586 reviews2019
    Dev: Dan FornacePub: Aether Studios
    Windows · Mac
    Median: 1.2 hrsMean: 27.7 hrs≥1hr: 57%

    Are you tired of fighting? Lovers of Aether is the game for you! This is a wholesome animal dating simulator set in the world of Rivals of Aether.

    Why similar: Dating Sim 58.6%, Visual Novel 26.2%, Romance 8.4%, Indie 2.3%, LGBTQ+ 2.1%

  35. #35 Fling with a Tiefling
    74% matchVery Positive92% of 83 reviews2024
    Dev: Kristi Jimenez
    Windows · Mac · Linux

    Fling with a Tiefling is a short fantasy romance visual novel that follows you, an adventurer whose journey is about to come to an end. With tonight potentially being the last night with your treasured Tiefling companion Karrus, how will you spend it with him?

    Why similar: Dating Sim 26.2%, Romance 22.8%, Visual Novel 21.1%, LGBTQ+ 14.3%, Multiple Endings 10%

  36. #36 The Man in the Park 2: The Second Man in the Park
    73% matchVery Positive90% of 87 reviews2025
    Dev: Elliott Dahle
    Windows

    It's been so long. You've tried to forget, however tonight you must walk through the park again. Now there are two men in the park. Will you help one, or both? Who will you trust?

    Why similar: Multiple Endings 39.5%, Adventure 21.8%, Horror 19.6%, 3D 12%, Indie 3.9%

  37. #37 Mission: It's Complicated
    75% matchVery Positive93% of 230 reviews2020
    Dev: Schell Games
    Windows · Mac

    Mission: It’s Complicated is a narrative-based, visual novel where you match super-awesome superheroes to go on missions during the night and dates during the day. The more compatible the pair of superheroes are, the more likely that they will fall in love and save the world.

    Why similar: Dating Sim 29.7%, Romance 22.8%, Visual Novel 18.2%, LGBTQ+ 11.8%, Cartoon 7.1%

  38. #38 The Femboy Next Door Thinks I'm Cute
    73% matchVery Positive79% of 61 reviews2024
    Dev: owlyboi
    Windows

    Coming home on a Saturday from the grocery store with little expectations, your roommate informs you that the femboy next door was looking for you...

    Why similar: Dating Sim 34%, Romance 21.4%, Visual Novel 20.5%, LGBTQ+ 13.7%, Adventure 4.7%

  39. #39 Monster Prom 3: Monster Roadtrip
    71% matchOverwhelmingly Positive97% of 3,273 reviews2022
    Dev: Beautiful Glitch
    Windows · Mac · Linux
    Median: 4.8 hrsMean: 7.2 hrs≥1hr: 93%

    Embark on a road trip like no other in this co-op narrative survival adventure. Visit fun locations, meet wacky characters, and manage your resources wisely. And yes: you still can date some hot monsters ;)

    Why similar: Dating Sim 33.1%, Visual Novel 19.9%, Romance 18.7%, LGBTQ+ 14.1%, Multiple Endings 10.6%

  40. #40 GemCrusty
    73% matchVery Positive89% of 134 reviews2023
    Dev: RedSensationGames
    Windows

    Dig, Discover, Date! Gemcrusty is a casual mining game, where precious gemstones are actually gems in human form.

    Why similar: Dating Sim 41.4%, Visual Novel 21.6%, Romance 17.8%, Adventure 11.6%, 2D 3.8%

  41. #41 Her World
    72% matchVery Positive97% of 481 reviews2022
    Dev: TALESSHOP Co., Ltd.
    Windows

    We invite you to experience this chillingly sweet romance.

    Why similar: Dating Sim 36.8%, Romance 24.2%, Visual Novel 23.2%, Horror 6.6%, Adventure 3.1%

  42. #42 Heirs And Graces
    75% matchVery Positive90% of 83 reviews2016
    Dev: Winter Wolves
    Windows · Mac · Linux

    Play as Marcel and determine whether or not he has the skills to become Lord Sandor's heir and whether or not he forms a romantic attachment to one of four potential love interests: an ex-gladiator turned gardener, a perfectionist butler, the local doctor, or a mischievous elven Lord.

    Why similar: Dating Sim 27.6%, Romance 21.7%, Visual Novel 18.2%, LGBTQ+ 14.5%, Multiple Endings 8.4%

  43. #43 Tri City Monsters
    71% matchVery Positive97% of 70 reviews2024
    Dev: Studio Peaches
    Windows · Mac · Linux

    Tri City Monsters is a supernatural, monsterlovin' visual novel where you can romance and/or de-pants 3 demonic love interests. Navigate a dangerous urban jungle with their help and maybe you'll get a taste of what it means to be a monster.

    Why similar: Dating Sim 30%, Romance 23.1%, Visual Novel 18.3%, LGBTQ+ 11%, Multiple Endings 9.2%

  44. #44 Love Sucks: Night Two
    70% matchVery Positive98% of 330 reviews2024
    Dev: Art Witch StudiosPub: Critical Bliss
    Windows · Mac · Linux

    This is Love Sucks:Night Two, the second part in your mission to get laid and not die doing it. When sexy monsters are out to kill you for their own mysterious goals, it's date or die! You've survived the first night, but can you survive your second?

    Why similar: Dating Sim 33.1%, Romance 23.4%, Visual Novel 18.7%, LGBTQ+ 12.7%, Adventure 5.4%

  45. #45 Paradise: Musubi
    70% matchVery Positive98% of 58 reviews2026
    Dev: PIL/SLASHPub: JAST
    Windows · Mac · Linux

    The first sequel to the Boys Love visual novel Paradise. Play through the continuation of the original game's good endings, and unlock flashbacks to the first Paradise from new perspectives. Contains new CGs, characters, and lots of romance!

    Why similar: Dating Sim 26.7%, Romance 24.5%, Visual Novel 22.4%, LGBTQ+ 17.1%, Adventure 6.2%

  46. #46 taking my Dark Knight Girlfriend to the corner store
    69% matchVery Positive99% of 293 reviews2025
    Dev: ForeverFuture Games
    Windows · Mac · Linux

    A beautiful Dark Knightess from another world enlisted me in her quest to slay a rogue wizard, and now we're dating! But what if she finds out I have no idea who the Gray Wizard is?!

    Why similar: Romance 34.1%, Dating Sim 21.8%, Visual Novel 19.8%, LGBTQ+ 16.7%, Adventure 5.9%

  47. #47 Extra Case: My Girlfriend's Secrets
    72% matchVery Positive86% of 173 reviews2022
    Dev: Sounding Stone / 老奉毊
    Windows

    Your girlfriend seems to be hiding something. Will you respect her privacy or pry into her secrets? Don't worry, though. This is a horror dating sim with a time loop, so you can try again...and again...and again...

    Why similar: Dating Sim 40.2%, Visual Novel 21.7%, Romance 16.9%, Adventure 6.1%, Horror 5.3%

  48. #48 Doodle Date
    74% matchMostly Positive73% of 338 reviews2018
    Dev: Nicholas Lives
    Windows
    Median: 2.2 hrsMean: 2.7 hrs≥1hr: 73%

    Romance, seduce, and even marry your own drawings! Forget about finding true love; In Doodle Date, you create it!

    Why similar: Dating Sim 33.8%, Romance 23.1%, Visual Novel 17.8%, LGBTQ+ 11.3%, Multiple Endings 10.2%

  49. #49 Furry Shades of Gay 2: A Shade Gayer
    71% matchVery Positive94% of 1,000 reviews2021
    Dev: Furlough GamesPub: Furlough Games PBS
    Windows
    Median: 3.9 hrsMean: 12.2 hrs≥1hr: 84%

    Furry Shades of Gay 2 builds on the first installment of the series to bring you even more love, more puzzles and more hot gay sex! Experience 6 new stories with an elaborate web of branching paths. Explore each one, win match-3 challenges, and get ready for hot animated VOICED sex scenes!

    Why similar: Dating Sim 25.7%, Romance 22%, Visual Novel 17.9%, LGBTQ+ 15.6%, Multiple Endings 11.8%

  50. #50 MindMindMind
    70% matchVery Positive97% of 76 reviews2024
    Dev: ChattercapPub: Chattercap LLC
    Windows · Mac · Linux

    A dark, psychological romance VN about a British ghost who has haunted you since childhood. When you get close to a new boy at college, he starts to get possessive, and the mind games begin!

    Why similar: Dating Sim 35.8%, Visual Novel 19.6%, Romance 17.9%, LGBTQ+ 13.8%, Multiple Endings 8.4%

  51. #51 I got STICKY with a FEMBOY
    69% matchVery Positive89% of 70 reviews2024
    Dev: owlyboi
    Windows

    Anticipation makes the "heart" grow fonder.

    Why similar: Dating Sim 33.1%, Visual Novel 22%, Romance 19.7%, LGBTQ+ 14%, Adventure 5.9%

  52. #52 boyfriend or cake??
    66% matchVery Positive94% of 112 reviews2025
    Dev: Nolan TaylorPub: Tactical Toad LLC
    Windows · Linux

    alternatively: caring romantic partner or delicious confectionery dessert?

    Why similar: Dating Sim 34.7%, Visual Novel 26.1%, Cartoon 18.7%, Romance 13.7%, 2D 4%

  53. #53 Something Strange
    69% matchPositive91% of 66 reviews2022
    Dev: Ethan ZimmerlePub: Mr. Hand
    Windows

    Go about your normal every day life and meet new friends in this short visual novel!

    Why similar: Visual Novel 59.6%, Horror 13.7%, 2D 11.1%, Adventure 8.9%, Singleplayer 3.8%

  54. #54 Plenty of Fish in the Sea
    67% matchVery Positive95% of 75 reviews2025
    Dev: Nullblade Studios
    Windows

    Plenty of Fish in the Sea is a cozy narrative-driven dating sim where you engage in heartfelt conversations with charming salmon and take them on delightful underwater dates.

    Why similar: Dating Sim 35.4%, Romance 22.3%, Visual Novel 14.8%, LGBTQ+ 14.4%, Multiple Endings 6.6%

  55. #55 Speed Dating for Ghosts
    68% matchOverwhelmingly Positive96% of 544 reviews2018
    Dev: Copychaser Games
    Windows · Mac
    Median: 3.3 hrsMean: 3.9 hrs≥1hr: 91%

    Branching dialogue! Hard choices! A cemetery's worth of phantoms, wraiths, and poltergeists lookin' for love in all the blight places.

    Why similar: Dating Sim 37.1%, Visual Novel 21.3%, Romance 19.8%, LGBTQ+ 14.9%, Horror 5.2%

  56. #56 Chair F*cking Simulator
    67% matchVery Positive94% of 1,076 reviews2020
    Dev: SoSorrySoft
    Windows
    Median: 18 minMean: 16.8 hrs≥1hr: 29%

    Use our innovative patented funky fresh ChairF*cker simulation tech to meet the chair of your wildest dreams.

    Why similar: Dating Sim 42.9%, Romance 30%, LGBTQ+ 16.9%, Horror 7.4%, Singleplayer 2.7%

  57. #57 Psycho地雷InLove : 싸이코지라이 인 러브
    67% matchVery Positive96% of 283 reviews2022
    Dev: 유진게임즈
    Windows

    A simulation of an outcast romance!

    Why similar: Dating Sim 44.6%, Visual Novel 24.7%, Romance 19.8%, Multiple Endings 5.9%, 2D 5%

  58. #58 My Cute Roommate 2
    66% matchMixed65% of 55 reviews2026
    Dev: Astaros3d
    Windows

    A wild 18+ visual novel about a guy with a huge cock, a snarky inner voice, lots of sexy girls, explicit scenes, spy intrigue, and crazy minigames. A new story in the MCR universe!

    Why similar: Romance 25.6%, Dating Sim 24.7%, Visual Novel 20.6%, Multiple Endings 12.4%, LGBTQ+ 9.9%

  59. #59 Trick and Treat - Visual Novel
    67% matchVery Positive90% of 3,613 reviews2016
    Dev: Eternal Night StudiosPub: Alberto Herrera
    Windows · Mac · Linux
    Median: 42 minMean: 5.1 hrs≥1hr: 41%

    Trick & Treat is a Visual Novel that test your instincts by making choices that can get you out from the cursed forest or drive you to death… or maybe just maybe your choices can guide you to something more?

    Why similar: Visual Novel 42.7%, Romance 21.5%, Dating Sim 19.6%, Horror 7.1%, Multiple Endings 3.8%

  60. #60 Paradise Lust 2
    65% matchVery Positive83% of 169 reviews2025
    Dev: Flexible Media
    Windows · Mac · Linux

    Continue your adventures on Tuvatuva island in a sultry 2D point-and-click adventure where romance blooms, puzzles are solved, and passion ignites in paradise.

    Why similar: Dating Sim 26%, Romance 22.8%, Cartoon 18.8%, Visual Novel 14%, Point & Click 7.6%

A Date With Chester 2 cover art

Games Like A Date With Chester 2

Based on tag similarity + player behavior
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