Simon's life has been a remarkable rollercoaster of angst and emotion. Growing up, he was an awkward kid, and his diminutive stature made him a prime target for bullies and ridicule. He battled through depression, self-confidence issues, and a general inability to fit in. More intelligent than most, he spent his childhood buried in books and computers, but he always yearned to be a part of the crowd and make personal connections with people, especially women.

Now, Simon is a middle-aged, devoted family-man, and loss redirects his life. He is ripped from introverted safety and thrust into the modern dating world. What follows is a tragically hilarious and sometimes raunchy string of bad dates with the wrong women. These new life challenges will test Simon's ability to cope and persevere and will force his next transformation.

For good or bad, he will finally become the version of himself that he has always wished for.