Rise (2008)

After the untimely death of Andy (Randy Spears), he's shown his past in the form of a highlight reel. His guide for this unusual demonstration Melissa (Kaylani Lei) politely provides the monologue and tries to help him see his former shortcomings. You see, Andy was never successful in love. Whether it was insecurity, work ethic or the after effects of a broken heart, he never found true love. But maybe this time, in the afterlife, with Melissa's guidance, he can rise to the occasion...