So, you’re thinking about a date with Miss Fortune. Honestly, the Bilgewater Bounty Hunter isn't exactly the "dinner and a movie" type unless the dinner is grog and the movie is a high-seas execution.
Most people know Sarah Fortune from her dominant presence in the League of Legends bot lane. She’s the red-headed captain who single-handedly turned Bilgewater from a chaotic pirate den into something resembling an organized, if still terrifying, city-state. But the fan-made visual novel, Date with Miss Fortune, takes that intense lore and pivots it into something surprisingly charming and weirdly stressful. It’s not an official Riot Games product, but it captures the spirit of the character better than some of the actual cinematics.
What Is Date with Miss Fortune Exactly?
It’s a fan-made dating sim. Let’s just get that out of the way.
Created by a small team of dedicated fans, the game places you in the boots of a nameless protagonist who somehow survives an encounter with the most dangerous woman in Runeterra. You aren't playing as Garen or some high-ranking noble; you’re just a person trying not to get shot. The stakes feel high because, in the lore, Miss Fortune isn't "waifu" material in the traditional sense. She is a ruthless tactician who watched her parents get murdered by Gangplank.
The game leans into this. It isn't just fluffy dialogue. You have to navigate her moods, her distrust of outsiders, and the general lethality of the Blue Flame Isles. If you say the wrong thing, you don’t just get a "game over" screen; you get a flavor-text description of why your character probably shouldn't have come to Bilgewater in the first place.
The Bilgewater Aesthetic Done Right
The art style is the first thing that hits you. It stays true to the gritty, barnacle-covered aesthetic of the Burning Tides event from years ago. You can almost smell the salt and gunpowder. The developers clearly spent a lot of time looking at the official Legends of Runeterra card art for inspiration.
The backgrounds aren't just static images. They feel lived-in. You see the jagged cliffs and the precarious docks that make Bilgewater such a unique setting in fantasy gaming. It’s messy. It’s loud. It’s dangerous.
Why Do People Keep Playing It?
Complexity. That’s the short answer.
Writing a "date with Miss Fortune" could have been a lazy exercise in fanservice, but the writers actually respected the source material. Sarah Fortune is a woman defined by her trauma and her ambition. She wants control. She wants revenge. Trying to find a romantic angle in that mess of a psyche is what makes the game compelling.
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You aren't "fixing" her. That’s a tired trope. Instead, you’re trying to find a moment of peace in her otherwise chaotic schedule of hunting down remnants of the Jagged Hooks gang.
The dialogue trees are surprisingly branching.
One choice might lead to a conversation about the heavy burden of leadership.
Another might end with a bullet in the dirt near your feet.
It’s unpredictable.
The Mechanics of Courting a Captain
Most dating sims are basically "press A to win affection." This one feels more like a tactical RPG disguised as a visual novel. You have to pay attention to what she says about her past. If you ignore her mentions of her mother’s workshop or the specifics of her pistols, "Shock" and "Awe," you’re going to fail the later skill checks.
It’s about respect, not just flattery.
Miss Fortune hates weakness. If you act like a subservient puppy, she loses interest immediately. If you’re too aggressive, she sees you as a threat. Finding that middle ground—being a capable partner who can actually keep up with her—is the "win condition."
Addressing the Elephant in the Room: Is It Canon?
No. Absolutely not.
Riot Games has been surprisingly cool about fan projects lately, provided they follow the "Legal Jibber Jabber" policy, which basically says you can’t charge money for it or pretend it’s official. This allows projects like Date with Miss Fortune to exist in a grey area. While it doesn't impact the ongoing lore of League of Legends or the Arcane universe, it fills a massive gap for players who want more character-driven content.
Official games like The Ruined King: A League of Legends Story gave us a great look at MF’s leadership style, but it didn't give us the "after hours" perspective. This fan game tries to imagine what Sarah is like when the guns are (mostly) holstered.
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Common Misconceptions About the Game
A lot of people think this is just a reskinned version of other dating sims. It’s not.
The UI is custom-built to look like the League client. The sound effects are pulled directly from the game’s library, giving it an eerie sense of authenticity. When you hear the "ping" of a notification or the specific sound of a gold coin dropping, it triggers a Pavlovian response in any long-time League player.
Another misconception is that it’s purely adult-oriented. While the themes are mature—Bilgewater is a place of crime and violence, after all—the writing focuses heavily on the emotional connection and the power dynamics between the characters. It’s more of a "noir romance" than anything else.
The Technical Side of Fan Projects
Running the game can sometimes be a bit of a hurdle. Since it’s not on Steam or the Epic Games Store, you usually have to find it on itch.io or similar indie hosting sites.
- Compatibility: It’s mostly built on the Ren'Py engine.
- Performance: It runs on basically any potato laptop.
- Updates: Since it’s a passion project, updates are sporadic.
Don't expect a polished, bug-free experience like you’d get from a Triple-A studio. There are typos. Sometimes the music loops awkwardly. But the heart is there. You can feel the developers' love for the lore in every line of dialogue.
What This Says About the League Community
The existence and popularity of a date with Miss Fortune highlight a major shift in the gaming world. Players aren't satisfied with just playing a match for 30 minutes and moving on. They want to live in these worlds. They want to know what their favorite champions do when they aren't on the Summoner's Rift.
The community is essentially crowdsourcing its own expanded universe. While Riot is busy making billion-dollar TV shows, the fans are in the trenches writing 50,000-word scripts about pirate captains and their favorite beverages.
The Difficulty Curve
Honestly, the game is hard.
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Most people fail their first "date" within ten minutes. The game expects you to have a baseline knowledge of the Bilgewater lore. If you don't know who Gangplank is or why the "Harrowing" is a big deal, you’re going to be lost. It rewards the "lore nerds" while being a bit unforgiving to casual fans.
But that’s part of the charm. It feels exclusive. It feels like it was made for the people who read the short stories on the Universe page of the Riot website.
How to Survive Your First Encounter
If you’re going to dive into Date with Miss Fortune, go in with a plan.
First, don't be a sycophant. Sarah Fortune has enough people bowing to her in Bilgewater. She wants someone who can hold their own. Second, listen more than you talk. The game hides clues in the dialogue that come back to haunt you later.
Lastly, remember where you are. Bilgewater is a city built on the bones of sea monsters. Every choice carries weight. Even a "simple" date involves navigating the political minefield of the docks and the ever-present threat of a knife in the back.
Final Thoughts on the Experience
Is it the best game ever made? No.
Is it a fascinating look at how fans can expand a corporate IP into something personal and weird? Yes.
Date with Miss Fortune succeeds because it doesn't try to make Miss Fortune "nice." It keeps her sharp edges. It keeps her ruthlessness. It just allows you to stand next to her while she navigates it all. It’s a testament to the depth of the characters Riot has built over the last decade and a half.
If you want to try it, search for the latest build on community forums or indie game repositories. Just make sure you’re downloading from a reputable source, as fan projects are often mirrored on sketchy sites. Stick to the primary developer's pages on itch.io or their official social media channels to avoid any malware issues.
Actionable Steps for New Players
- Brush up on the lore: Spend twenty minutes reading Miss Fortune’s bio and the Burning Tides story on the official League of Legends Universe site. It will make the dialogue choices much clearer.
- Download from the source: Only use the official developer links (usually found on Twitter/X or itch.io) to ensure you have the most stable version of the game.
- Save often: The branching paths are real, and you will make a mistake that ends the story prematurely. Use multiple save slots before major dialogue decisions.
- Pay attention to the background: Sometimes the "correct" choice is hinted at by the environment or the subtle changes in Miss Fortune’s character sprite.
- Check for community patches: Since it's an indie project, fans often release small fixes or "quality of life" mods that make the UI much easier to navigate.