Western Crossover: The Dating Game

Dear Cybella,

You're trapped in a virtual dating game. To return to reality, you have to achieve five perfect Happy Endings. The way to clear the game is simple: get every suitor's affection for you up to 100%.

The producer has three reminders for you:

1. It's a dating game, but you're the one being pursued.

2. It's a dating game, but it's Soulslike.

3. The characters are random. The final reckoning begins after you achieve 100% affection five times.

The first character to appear is: [Roman Sionis (Black Mask)]

Cybella: ...?

Cybella: How do I fall for a disfigured, masked villain like this? Teach me.

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I'm going straight for a crossover extravaganza, with a chaotic, all-over-the-place world that may not make complete sense. For now, I'm planning to include The Boys, John Wick, Fight Club, Twilight (?), and My Week with Wayne (???).

One more friendly reminder from the producer:

1. The characters who appear may or may not be the main character of that round.

2. The remaining four unlucky guys are yet to be decided.

3. This game is as hard as Bloodborne (yes, it's a dating action game).

4. More to be added as I think of it.

Theme: Ruin yourself by falling in love