Nick Forrester - The narrator of the story. At 26 years old, he runs a fairly successful web design business with his friend Jay. He's recently ended his relationship with his long-term girlfriend, and still struggles to come to terms with it. Following a one-night-stand (which he regrets immediately) he realizes he's ready to get back out there. Soon after he becomes smitten with Alli Conwell and they start dating.
Alli Conwell - A Starbucks barista and up-and-coming singer/songwriter who starts dating Nick after he sees her opening for the band Candlepin. She's only nineteen years old, but extremely talented, and hopes to support herself entirely with her music. She's innocent and shy, and very secretive about her life before moving to Boston.
Devon O’Connell - Nick's promiscuous roommate who's responsible for setting Nick up with her friend Emma to help him get over his ex. She's a professional photographer who takes her camera with her almost everywhere. Her personality often clashes with Alli's.
Jay Wright - Nick's friend and business partner. They used to work for the same company. When they were laid off they started their own business. They don't always agree on business decisions, but their business is growing. He's and his roommates are avid gamers with an affinity for retro video games.
Blake Kelly - Keyboardist for the band Candlepin. He helps Alli make connections to advance her music career and occasionally shows up at her gigs, making Nick suspicious of his intentions.
Lacy Walker - Nick's teenage half-sister. Nick has struggled to connect with her because of the twelve-year difference in their ages.
Lauren Petrakis - Nick's ex-girlfriend. When Nick proposed to her on New Year's Eve she was overwhelmed with guilt for having previously cheated on him and tells him about the infidelity, prompting him to end their relationship.
Emma Burke - Devon's friend who has a one-night-stand with Nick. She's going to school to be an architect and waitresses on the side