Filling a Void (Kendall Jenner X Male Reader)

You're a man who's had a streak of bad luck when it comes to love. Nothing seems to work out, and everything always goes wrong in the end. You feel like there's nobody out there for you. But one day, a woman walks into the bar and it changes everything...

Inspired heavily by TattoedC3P0, who wrote a series much like this that seemingly was discontinued :((