Two of his friends help him improve his life and outlook. He is first introduced to Maria, a divorced mother and struggling writer to whom he eventually becomes engaged. Sadly, this relationship fails, and Eddie then focuses upon building his own specialized insurance business. Andy, one of his friends, a health IT specialist with a shady past, tries to help Eddie by illegally supplying private health information about potential clients to help him build his business. At first Eddie is reluctant to accept Andy's help, but eventually, his desire to succeed, his past struggles, and Andy's constant encouragement and belief that he is only helping Eddie help others turn Eddie into a passive recipient of information he should not have had. And this where the plot thickens.

Beyond the shocking details of how easily hospital employees can access private health information for nefarious purposes, Rainy Day Comrades is an introspective look at one man's challenging journey through life, and the relationships that have shaped it.

While his business begins to take off, Eddie begins a relationship with Flora, also a health IT specialist who works with Andy. Flora falls deeply in love with Eddie and is horrified when she eventually learns of Andy's scheme and Eddie's role in it. She breaks off the relationship and Eddie is left very much where he had been before meeting her. Having failed once again, Eddie decides to give up on life in Chicago, and decides to return to Guam, where he feels more comfortable surrounded by family and without the pressure to succeed. Eddie then feels the heavy loss of Flora, and persists in trying to reconnect with her, eventually succeeding, and finding peace.

Beyond the shocking details of how easily hospital employees can access private health information for nefarious purposes, Rainy Day Comrades is an introspective look at one man's challenging journey through life, and the relationships that have shaped it.