Diego is a 16 year-old boy with a problem. He loves his girlfriend, Roxy. And when they suddenly break up due to Diego's insecurity issues, the boy is crushed. How ever will he win Shorty back? On the trusty advice of his (crazy) best friend, Diego invents an alter ego known as Dr. Truelove. A sex and relationship e-columnist, Truelove is smooth where Diego is gawky, skilled where Diego is clueless. Truelove is, quite clearly, the way back into Roxy's heart. Or so it seems...