Being Erica (2009)

"Therapist" Dr. Tom - who is constantly spouting famous and not so famous historical quotes - is Erica Strange's savior and worst enemy. Erica, a young adult woman, is having a bad life because of the bad decisions she's made. Erica provides Dr. Tom with a long list of those pivotal moments in her life that she feels have led to the bad state she is in today. Erica is initially unaware of what Dr. Tom is intending on doing with this list. What he does do is transport her back in time to each of those moments so that she, with all the knowledge of her present day life, can make better decisions to fix her life. Regardless of these new decisions, Dr. Tom hopes that Erica will come to the realization that although the opinions of others about her life do matter, it's what she thinks of her decisions and her life that are more important.