The Dating History of ‘Teen Mom OG’ Star Amber Portwood

Romantic highs and lows. Over the years, Teen Mom OG star Amber Portwood has seen her fair share of relationship drama, but she has never given up on love.

The reality star's first significant relationship was with Gary Shirley, with whom she had a daughter in November 2008. Shirley popped the question before Leah's birth, but the pair finally split in 2011 after their numerous heated arguments were shown on both 16 and Pregnant and Teen Mom OG.

After losing custody of her daughter in 2011, Portwood was sentenced to jail in 2012 for a cocaine conviction in December 2011. After her release in November 2013, she and Shirley decided to share parenting in 2015, provided he retained primary physical custody.

In 2014, Portwood met her next lover, Matt Baier, on Twitter; however, it was soon found that he had been texting other Teen Mom stars as well. While the television personality became engaged to the notorious DJ in 2015, the former pair had their share of turmoil, including the revelation that the native of Massachusetts had fathered at least five children.

Gary Shirley

After meeting in high school through Portwood's brother, the Teen Mom OG stars began dating and welcomed their daughter Leah in November 2008. Shirley acquired primary custody after many arguments and a 2010 confrontation that culminated in Portwood's detention.

The Dating History of Amber Portwood

Due to Portwood‘s legal difficulties, the couple struggled to co-parent Leah calmly, but they've managed to turn things around in recent years. In March 2022, when her ex underwent surgery for carpal tunnel disease, the television celebrity also sent him a message of support. In the process, she also mentioned his now-wife, Kristina Shirley.

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Matt Baier

After contacting Baier on Twitter in 2014, the MTV star moved on to Baier. Even though they became engaged in 2015, the Las Vegas native's questionable background was shortly revealed when he acknowledged fathering many adult children with multiple women. In 2017, the couple broke up while shooting Marriage Boot Camp Reality Stars: Family Edition.

The Dating History of Amber Portwood

In August of 2017, he told “I'm trying to do a lot of work on myself because I recognize that the demise of our relationship was my fault.” “Being forced into the limelight in such a manner might have repercussions. My error was taking our connection for granted.”

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Andrew Glennon

In 2017, Portwood met Glennon, who worked on the series, while filming Marriage Boot Camp. James was born to the reality star and the California native in May of 2018. The couple's relationship deteriorated in July 2019 when Portwood was arrested for domestic violence. In July 2022, Glennon was awarded sole custody of the child.

The Dating History of Amber Portwood

Following the verdict, Portwood expressed her sadness openly. “I have worked so diligently to improve myself and my relationships with my children. She told Us, “A person should have the opportunity to redeem themselves and not be chained to their prior faults.”

Dimitri Garcia

The 16 and Pregnant star began dating the Belgian in January 2020, and he appeared on Teen Mom OG for the ninth season in 2021. Even though Portwood told in February 2021 that they were not “boyfriend and girlfriend,” she insisted that they were still “talking” as a long-distance romance.

The Dating History of Amber Portwood

“My entire attention right now is on my personal development and my children,” she explained.

During a polygraph test scenario in Teen Mom OG season 7, it was discovered that while Baier was physically faithful during their relationship, he made sexual overtures toward an unknown lady. In the summer of 2017, Portwood ended her relationship as a result of these revelations while filming Marriage Boot Camp: Reality Stars Family Edition.

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During her time working on Marriage Boot Camp, the author of Never Too Late met Southern California cinematographer Andrew Glennon. As soon as the couple started dating, the MTV personality became pregnant with her second kid, James, who was born in May 2018. A year later, the 16 and Pregnant alum told Us that Glennon was her “soulmate” and described him as a “beautiful person.”

Portwood was arrested in Indiana during the Fourth of July holiday weekend of 2019 for allegedly assaulting Glennon while he was holding his son. According to the Indy Star, she pled guilty to two felony charges of domestic assault and intimidation.

Portwood subsequently accepted a plea bargain in the case, but in July 2022, Glennon was awarded primary physical custody of James following a violent custody fight. Additionally, he was permitted to relocate James from Indiana to California.

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