The reality star’s first serious relationship was with Gary Shirley, with whom she welcomed daughter Leah in November 2008. Shirley popped the question before Leah was born, but the couple ultimately separated in 2011 after their many tumultuous fights played out on both 16 and Pregnant and Teen Mom OG.
After Portwood lost custody of her daughter in 2011, she was sentenced to jail in 2012 following a December 2011 drug arrest. Following her November 2013 release, she and Shirley agreed on splitting custody in 2015, so long as he retained primary physical custody.
Portwood met her next boyfriend, Matt Baier, via Twitter in 2014 — though it was soon revealed that she wasn’t the only Teen Mom star he had been messaging. While the TV star became engaged to the controversial DJ in 2015, the former couple had their fair share of drama, including when it came to light that the Massachusetts native had fathered at least five children.
During a polygraph test scene on season 7 of Teen Mom OG, it was revealed that while Baier was physically faithful during their relationship, he made sexual advances towards an unnamed woman. Following those findings, Portwood ultimately broke things off while in the middle of filming Marriage Boot Camp: Reality Stars Family Edition in summer 2017.
During her time on Marriage Boot Camp, the Never Too Late author met Andrew Glennon, a Southern California cinematographer who worked on the series. After the two began dating, the MTV personality quickly became pregnant with her second child, James, who arrived in May 2018. The following year, the 16 and Pregnant alum told Us that Glennon was her “soulmate” and called him a “beautiful person.”
Over the 4th of July weekend in 2019, Portwood was arrested in Indiana after allegedly becoming violent toward Glennon while he was holding their son. She pleaded guilty to two felony charges of domestic battery and intimidation, according to the Indy Star.
Portwood subsequently accepted a plea deal in the case, but after a brutal custody battle, Glennon was awarded primary physical custody of James in July 2022. He was also granted permission to move James from Indiana to California.
“We endured the nightmare,” Glennon told E! News in July 2022 after the official court ruling had been made. “Now we get to live the dream.”
For her part, the So You’re Crazy, Too? author told Us Weekly that she will “never stop fighting” for her kids whom she “loves more than anything.”
“While I’ve always been candid about my past substance abuse and struggles with mental illness, a person should have the chance to redeem themselves and not be tethered to their problems from the past,” Portwood argued, noting she had submitted “21 negative drug tests and under[went] multiple psychological evaluations” for the custody case.
Scroll down to find out more about Portwood’s dating history: