The course of love never did run smooth. On again-off again lovers, Gia and Logan, find themselves at a crossroads when a long-distance relationship makes them to confront their innermost desires. When longtime bachelor, Ryan, finally decides to settle down and propose to his girlfriend, he is in for a surprise when she tells him that she thinks marriage is a bad idea. Derrick hatches a plan for a one-of-a-kind proposal after he falls desperately in love with his one-night-stand. After a series of roadblocks prevent Tyler from proposing to his Adria, he fears neither of them will ever have their "happily ever after."