In the years since fans first met Amber Portwood on 16 & Pregnant, they have seen her experience some of life’s most beautiful moments — and been there for her hardest times too.
Three years into her relationship with boyfriend Gary Shirley, the Indiana native learned that they were expecting their first child in 2008. He popped the question shortly before daughter Leah Leann Shirley was born in November 2008. Their first few years of parenthood were chronicled on both 16 & Pregnant and Teen Mom.
However, their relationship soon turned rocky, with many of their fights, break ups and make ups playing out on reality TV. One of those fights, which was captured on camera, resulted in Portwood being arrested in December 2010 and charged with two felony counts of domestic battery, one felony count of neglect of a dependent and one misdemeanor count of domestic battery. She spent the night in prison and was barred from having any contact with Gary.
Over the years, Portwood has been open about her struggles with mental health and substance abuse. In addition to her domestic violence arrest, the MTV personality served 17 months in prison after violating her probation in her December 2011 drug possession case. “I have really horrible anger problems because I’m bipolar and borderline, which is not an excuse, but at the time I didn’t know it, so I wasn’t really taking care of myself or really understanding why I was feeling certain emotions,” she revealed during a 2018 interview with the “Dopey” podcast, adding that hard partying often led to her violent outbursts and that her TV money often went to drug dealers.
“When you’re making a lot of money, there’s more drugs,” Portwood explained. “Every time a drug dealer had a new stash, of whatever, they called me first because they knew I’d buy the whole [stash], because I had the money to do it. It never helps.”
Things seemed to turn around for her after she committed to getting clean, and she got engaged to on-off boyfriend Matt Baier in April 2015. Just over two years later, however, Portwood confirmed during an interview with Us Weekly that she and Baier had split. “We’re not together right now,” she exclusively revealed in June 2017. “At this point, I told him it’s pretty much up to him to save this relationship.”
While filming Marriage Boot Camp with her ex-fiancé, Portwood met cinematographer Andrew Glennon, who she later began dating. “We’re going slow and we’re just trying to be smart about everything, which is good to find somebody on your level like that,” she told Us in August 2017. “I think we just kind of fell into this groove really enjoying life with each other for a while, so it’s kind of fun and it’s kind of serious in a way as well. But we’re trying not to put too much pressure on a relationship.”
In November 2017, Us confirmed that the Never Too Late author and Glennon were expecting a baby boy. The couple welcomed son James in May 2018. “[Andrew] is such an amazing man and loves taking care of James,” Portwood gushed to Us one month later. “He was afraid of postpartum depression, so he’s always checking up on me. He just wants to make sure I’m loved. It’s almost perfect.”
Just over one year later, Portwood was arrested again on felony domestic battery charges after a disagreement with Glennon turned violent. She ultimately took a plea deal, receiving one felony charge for the incident and agreeing to one year of probation. In July 2022, Glennon was awarded sole custody of James after nearly three years of battling for custody.
“I’ve worked so hard to better myself and improve my relationships with my children,” the Indiana native told Us in a statement at the time. “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. I’ve spent years rebuilding bridges and did everything that was required of me, including submitting 21 negative drug tests and undergoing multiple psychological evaluations, if your road has not been perfect, but you’ve worked hard to become a better, more stable and caring person today, keep moving forward as I will.”
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Keep scrolling to relive Portwood’s ups and downs over the years: