Hear me out… 10 Unhinged Dating Sims for a Wild Ride

All romance starts with a little intrigue. A first glance, a flicker of awkward tension, and the classic will-they-or-won’t-they before a happily ever after. These titles take the same formula and run through it with wild abandon.

As a general rule: there’s one character who wishes to find romance and that’s you.

That’s all the normalcy these titles can offer, as they can truly go off the rails. They not only break stereotypes of who and what can be romanced, but also how. 

The experience can be an avenue to explore the spectrum of love, but opt more towards absurdism with a golden, gooey heart at the core.

Note that these titles are not appropriate for all ages. Ratings are based on current ESRB or Steam scores. Tread with caution. 

Whether the strangeness stares right in your face, or hides in the shadows when you’ve fallen too deep, there’s much to discover about the mysteries of courtship in these 10 unhinged dating sims that has to be prefaced with: Okay, hear me out…

Sucker for Love: First Date (Teen)

Available on PC (Windows, macOS); Consoles (Steam Deck, Switch 1/2)

The package finally arrives. Within the box is a book feared by the wisest and strongest mortals. But something’s a bit different here because the ancient grimoire is bright-pink. The forbidden text containing rituals and ways to summon horrors from beyond the veil is… a lovely color!? 

What follows is an innuendo-filled spin on eldritch horror where instead of climbing out of a crypt at midnight, a flirty tentacled entity (that you) recently summoned is ready to give you a kiss. But not without a tiny little insignificant favor where defiance could only mean the collapse of all reality. No big deal.

Of course, you oblige. It’s the curse of the fourth dimensional curves talking. (Besides the other voices whispering in your ear.)

Try to keep your sanity intact in this meet-cute creature feature in a time of horrors beyond comprehension. 

Kaichu – A Kaiju Dating Sim (Teen)

Available on PC (Windows, macOS); Consoles (Steam Deck, Switch 1/2)

Breaking news: a kaiju has landed near the North Pole. This time, it’s not destruction they’re after, it’s love. Meet Gigachu, a skyscraper-sized monster with a heart big enough to fit another city-stomping sweetheart. 

The benefits of dating as megabeasts are pretty clear: international travel anywhere, anytime. Fancy a date by the Eiffel Tower? Or maybe a spiritual experience at Angkor Wat? Distance is no obstacle when continents are a few strides away. 

Since kaiju don’t talk at all, courtship involves flattening famous monuments and fighting a robotic menace. A pair of news anchors report their every move and assist with the seismic flirtation to see if the two colossals are compatible. 

An uncomplicated, light-hearted experience where the spectacle of dating leaves rubbles behind. 

Date Everything! (Mature 17+)

Available on PC (Windows, macOS); Consoles (Steam Deck, Switch 1/2, PS5, Xbox Series X/S)

You’re staring at the ceiling at 3 AM, feeling lonely. Every wish you could… just maybe… date… the ceiling?! Or, if you’re feeling bold, how about the stairs? 

Through a fresh pair of special lenses, house objects become ‘dateables’. You can also build relationships with intangibles like, say, Overwhelming Sense of Existential Dread or even Electricity. There’s 103 characters that you can meet in your own house.

While the premise pushes the boundaries, some routes sneak in moments of sincerity, giving a glimpse into what it means to connect, be seen, and be taken or taken for granted. 

Home is a place to build love, friendship, and even hatred across a cast of fully-voiced, quirky personalities. Now, is the vent happy to see you or is it just air blowing through?

This is the latest title in the list, alongside Monster Prom 4.

Boyfriend Dungeon (Teen)

Available on PC (Windows, macOS); Consoles (Steam Deck, Switch 1/2, PS5, Xbox One, Xbox Series X/S)

Apart from the object of desire being a weapon of destruction that can turn human, this title is a dating sim and dungeon crawler in one. Go against antagonists using a variety of weapons that you can wield and woo at the same time. 

Enter the dungeon to face your fears, earn affection, go on dates, return to another dunj, and drink some boba tea. The more you romance each weapon, the more powerful they become in battle.

In this fantasy, love is a force that you can wield according to your preference. Like any battle, it’s necessary to keep your armor up, because relationships here can be double-edged. 

Best to listen to advice from Mom when she says: “Stay on your guard, okay?”

Hato Moa, whose brainchild is Hatoful Boyfriend, is one of the character designers for this title.

Dream Daddy: A Dad Dating Simulator (Teen)

Available on PC (Windows, macOS); Consoles (Steam Deck, PS4/PS5, Switch 1/2); Mobile (Android/IOS)

Finally, a dating sim where you get to spend time with an emotionally available father (non-derogatory). You play as a pretty good single dad yourself to a teen named Amanda. The two of you just moved to a new city.

Between settling in, walking around town, and asking what a meme is to which you’ll get the you just don’t get it, dad, you’ll meet other dads who may or may not become more than just neighbors. 

Dad jokes and puns aside, conversations lean into cool dad territory: art shows, record collections, and obscurish references. But who’s the daddiest of them all? A cute minigame might sort it out. Otherwise, let your vulnerability take you to parts perhaps previously unknown.

In proper dad manner, always stretch before doing anything physical. Your knees aren’t what they used to be. (In reference to being invited for golf…)

Speed Dating for Ghosts (Teen)

Available on PC (Windows, macOS); Consoles (Steam Deck, Switch 1/2, Xbox One); Mobile (iOS)

In hell, drinks are free. Before that, take a long sip: death here is not a topic that’s off the table. Even for a first date.

This charming yet dark experience is an existential spin on speed dating. Meet a set of initially scary-looking dates, where familiarity removes the spook factor and what you’re left with is a set of fun, stirring stories that can also break your heart. 

A little bit like Vampire Therapist, where even in the afterlife, the dead crave for insight and connection, romantically or otherwise. 

It’s a great way to try out speed dating where the worst that can happen, which is to literally pass away during a date, is already out of the way. There’s much to discover here even when everyone’s dead.

If death is a touchy subject or if you’re grieving, it’s best to shelve this for now.

Doomsday Paradise (Mature 17+)

Available on PC (Windows, macOS); Consoles (Steam Deck, Switch 1/2)

Speaking of the afterlife, this title sits right on the cusp of it. The world ends in a matter of days, but no one in Sunset Town seems too bothered. No need for panic when you can grill meats and crash parties that could lead to romantic entanglements right before it all comes crashing down.

You’ll mingle with a colorful mix of characters with a solitary essence they keep throughout the (end of) time. Is it simply denial or a flair for hedonism evidenced in a general lack of shirts and/or pants? Or perhaps it’s willful acceptance? 

Doomsday could be a block party with a multiplayer option. It also has deck-building mechanics and high replayability. There’s over 100 different endings, with countless branching scenarios.

The end is nigh, and romance is ticking down to the final seconds. 

Monster Prom 4: Monster Con (General Mature Content)

Available on PC (Windows, macOS); Consoles (Steam Deck, Switch 1/2)

Ahh, a setting teeming with so many possibilities: a monster convention. Returning with its fourth installment, the Monster Prom series reunites you with familiar faces Zoe and Liam, while introducing four new characters to romance.

Chase your nerdiest fantasies by winning a heart before the Con wraps up. Like any con, time runs short with countless distractions. The romance unfolds through a whirlwind of cosplay, contests, attending panels, and snack-fueled encounters. 

Choose wisely to gain stats that progress the plot towards a desired outcome, or it can all come to a close.

Charming, hilarious, spicy. Among the boldest of the bunch, featuring suggestive language, often with a bonus for the more… visual learners.

Purrfect Date (Unrated, most likely 12+)

Available on PC (Windows, macOS); Consoles (Steam Deck); Mobile (IOS)

You’ve been hired as a research assistant for the team assigned to work on mysterious Cat Island. Up to that point, you were a broke student living off baked beans. 

Closer now, the black land mass from the distance is coming within reach. A secret location isolated from most of humanity, populated by more felines than human counterparts. Totally normal, nothing suspicious about that at all!

But almost immediately after arriving, your fate will have been decided. 

Between working as a researcher and finding the solution to your predicament, you will also talk with a number of felines. First as friends, then later if you’re lucky, maybe a life partner. 

A visual novel with an interesting storyline and lovable characters, feline and human alike. Play for a love of cats that transcends mere servitude.  

Hatoful Boyfriend (E10+)

Available on PC (Windows, macOS); Consoles (Steam Deck)

What began as a concept for an April Fool’s joke on July 31, 2011 became an enduring presence in both the visual novel and dating sim genres. It was then released as a remake in 2014 on Steam. 

You are the only human attending St. PigeoNation’s Institute, where you’ll meet potential avian love interests as a student. Bump beaks with schoolmates of your fancy, and find out what it feels like to flirt with feathered faculty members. 

You’ll be accompanied by your beady-eyed friends even on the long, twisting journey into a dystopian future of bird supremacy. 

If pigeons don’t do it for you, fall in love instead with the sheer audacity of the premise and exceptional writing of this visual novel that nonchalantly shifts from aww to ha-ha to what the—!

A masterclass in parody that soars into an experience worth remembering. 

Risk it all for the unconventional romps in these titles. If you decide to take the plunge, do it with all your heart (sanity optional). Don’t worry… no judgement here.