Rayna Jaymes and Juliette Barnes face personal and professional challenges as they navigate their paths as artists and individuals. Surrounding them, and often complicating their lives, are their family, friends and, in some cases, lovers, as well as the up-and-coming performers and songwriters trying to get ahead in the business.

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.