Oldest paid games for macOS tagged Dating Sim

Explore games for macOS tagged Dating Sim on itch.io. Dating sims (or dating simulations) are a video game subgenre of simulation games, usually Japanese, with romantic eleme · Sell your games for macOS on itch.io to have them show up here.

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A tale of unrequited e-mail.

Oh, a Rock! Studios

Visual Novel

Destiny Fails Us: A New Life

$10

It's time to start a new life.

Strawberry Dagger Studio

Visual Novel

Bitch Shark

1€

A complicated love story between you and a mutant-shark-girl

RisingPixel

Visual Novel

Play in browser

Serafina's Crown

$7.99

Rule Darzia. Face the gods. Follow your heart.

Woodsy Studio

Visual Novel

Blind Love

A man struggling with love without sight.

Michaela Laws

Visual Novel

Social Interaction Trainer

Learn how to conduct yourself in social situations.

googumproduce

GIF

Aurora Memoria + Original Soundtrack

$3.99

What is love to the digital soul of a species?

Priz Tats

Visual Novel

GIF

A Wild Catgirl Appears!

$2.99

A Romantic Catgirl Adventure!

NewWestGames

Visual Novel

Seduce Me 2: The Demon War

$4.99

The Sequel of Seduce Me the Otome, where you not only deal with romance, but with a full-fledged World War...

Michaela Laws

Visual Novel

GIF

Snow Cones: Episode 1

$2.70

-10%

A frozen treat dating simulator

TeamLazerBeam

Simulation

My Lady

A short story of a lady in love with her butler...

Michaela Laws

Visual Novel

Hustle Cat

$20

A Dating Sim in a Cat Cafe with a Magical Twist

datenighto

Visual Novel

Celestial Crossing

$3.99

Would you get along with your game character?

Touwaku

Visual Novel

GIF

Wrestling With Emotions

$2.70

-10%

Quest For The Perfect Match

TeamLazerBeam

Simulation

GIF

Dress To Express Dancing Success

$1.80

-10%

An awkward dancing, dating simulator about trying to fit in.

TeamLazerBeam

The Rock and The Rock

Two Rocks — One Attraction

Kevin Roark Jr

Interactive Fiction

Rose of Winter

$10

Four handsome fantasy princes need to cross a mountain pass, and you, Rosemary, are the knight for the job!

pillowfight

Visual Novel

SoulSet

$16.99

A Mystery/Romance Visual Novel, with pursuable male and female characters.

NoBreadStudio

Visual Novel

Chronotopia: Second Skin

$24.99

A unique rewriting of the Donkeyskin fairytale, a darker variation of Cinderella.

Traumendes_Madchen

Visual Novel

Blind Men

$3.50

A boys' love visual novel about a supervillain and the spies that try to stop him.

Man-Eater Games

Visual Novel

Valentine Panic!

A short romance visual novel/dating sim

Michaela Laws

Visual Novel

Wilder: Ran's Story

$3.99

a forbidden romance

sonnet009games

Visual Novel

IN THE ARMS OF THE NIGHT

£2.40

A novel-length "bat-romance" Twine.

polymer despair

We Know the Devil

$6.66

A Group Relationship Horror Visual novel.

pillowfight

Visual Novel

Demonheart

$19.99

Dark fantasy romance, lots of dialog choices.

Rolling Crown

Visual Novel

Ghosts of Miami

$15

A mystery VN set in 1980s Miami, featuring a softboiled detective with a heart of gold. Solve crimes, kiss ladies & men.

pillowfight

Visual Novel

GIF

Emily is Away Too

$4.99

Message your friends, surf the web and choose your path through this brand new narrative.

kyleseeley23

Visual Novel

Heaven Will Be Mine

$15

Joyride a mecha. Sext your enemies. Fight the pull of gravity.

Visual Novel

The World's greatest ice-cream-cone romance-saga continues!

TeamLazerBeam

Bionic Heart

$9.99

A mature dark sci-fi space opera with 24 different endings

Winter Wolves

Visual Novel

Always Remember Me

$17.99

An accident, amnesia and his ex. Will you fight back or date someone else?

Winter Wolves

Visual Novel

Never Forget Me

$14.99

Love stories don't end with marriage...can you reach your happily ever after?

Winter Wolves

Visual Novel

Spirited Heart Deluxe

$19.99

Winter Wolves

Visual Novel

Nicole

$18.99

Find romance and uncover the mystery of the missing girls

Winter Wolves

Visual Novel

C14 Dating

$19.99

Winter Wolves

Visual Novel

Flower Shop: Summer In Fairbrook

$9.99

Winter Wolves

Visual Novel

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Oldest paidGamesGamesToolsGame assetsComicsBooksPhysical gamesAlbums & soundtracksGame modsEverything elsefor macOS tagged Dating Sim (202 results)

New itch.io is now on YouTube!

Oldest paid
Games Tools Game assets Comics Books Physical games Albums & soundtracks Game mods Everything else
for macOS tagged Dating Sim (202 results)