New Yorker Jerry Needleman was married for over 40 years when his wife passed away in 2008. The devoted couple never had children, and now in his 80s, Jerry settled into a quiet life alone as a widower. Meanwhile in Florida, a woman named Sylvia is pursuing a relationship with a retiree. The man has spent thousands of dollars on his much-younger girlfriend. When they become engaged, the man's son steps in. In 2012, the family successfully sues Sylvia for fraud. One year later, Jerry is out for his daily walk when he comes across a distraught woman crying on a park bench. The woman is Sylvia. Jerry stops to see if she is OK, unknowingly embarking on what will be a four-year ordeal that includes a marriage, a divorce, a second marriage and annulment — and nearly $2 million lost to a romance scam.