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.

Malcolm and Sofia, two determined teens from the Bronx, are the ultimate graffiti-writers. When a rival gang buffs their latest masterpiece, they must hatch a plan to get revenge by tagging an iconic NYC landmark, but they need to raise $500 to pull off their spectacular scheme. Over the course of two whirlwind, sun-soaked summer days, Malcolm and Sofia travel on an epic urban adventure involving black market spray cans, illicit bodegas, stolen sneakers, a high stakes heist, and a beautiful, stoned girl whose necklace is literally their key to becoming the biggest writers in the City.