He Shoulda Known

Craig fancies himself a romantic and yet he has never fully learned how to understand women. Oh, he thinks he does, but he has never been able to make a relationship work for long. He would say he's cursed with bad luck. Others, like his best friend, Brittany, would say he just has no idea what is good for him. She was one of his earliest failures. But at least she has stayed by his side as a confidant and occasional hook-up partner. Knowing she'll always have his back is why he entrusts her with what he feels is the perfect plan to win the heart of Raylen, the latest object of his desire. Everything is under control until their friend Erica, an essential part of the scheme makes a request to secure her cooperation. Craig finds himself in a dream scenario, a chance to be with not just two women, but one who had seemed like an impossibility for so many reasons. But all is not as simple as it first appears when the two women show up at his apartment. Before the first stitch of clothing is removed, it becomes clear that Craig isn't the only one with a plan in the works. He now finds himself in an emotional conflict as the innocent night of fun becomes something far more serious than he had ever expected.