Michael met his future wife Amanda when she was working as a stripper at a strip club. After flirting with each other, the couple started a romantic relationship. Using money earned from illicit activities, Michael was even able to buy Amanda some breast implants, which would help with her stripping career, as well as her stint as a prostitute. This led to Michael creating his own prostitution racket. After a few months of dating, Amanda became pregnant with their two children Jimmy and Tracey while living at a trailer park in the Midwest. A few months later, they got married. Michael began to see that he had a lot more to lose if he was ever killed or imprisoned and started to keep to himself over time as a criminal and was much more careful much to Trevor's annoyance, who saw Michael as "soft". A few years later, Trevor met Brad Snider, a fellow crook and future accomplice of Michael and Trevor. Michael and Brad would never show any empathy for each other and would often express distaste or distrust when working together. According to Trevor, Brad planned at one point to cut off Michael and work solely with Trevor.

While living in North Yankton, Michael had a stronger bond with his loved ones and they were able to get along with each other. But after relocating to Los Santos, Michael's obsession with living the Vinewood Dream along with his depression about having to abandon his criminal lifestyle made him neglect and alienate his family, while he himself became egocentric, selfish and conceited. Early within the storyline, Michael will be seen constantly fussing, bickering and arguing with his family up until the mission Did Somebody Say Yoga?, where they'll abandon him in search for a more peaceful living. After Michael reunites with his family in the mission Reuniting the Family, Michael will be seen bonding with them much more often than before, as they all promise to fix up their relationship with each other before things become disastrous. While hanging out with Amanda, Michael admits that he thought he lost his family for good once they left him and that made him eager to change his ways.