Rachel Boston

When notorious womanizer Connor Mead attends his brother Paul's wedding, he is forced to re-evaluate his behavior as he comes face-to-face with the ghosts of girlfriends past, present, and future, along with his deceased uncle. The experience changes his attitude and allows him to reconnect with his first and only love, Jenny.

Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.