'Teen Mom' Amber Portwood Has Had a Rocky Relationship Past — Here's a Breakdown of Her Dating History

Anyone who follows the world of MTV reality stars is likely to know quite a bit about Amber Portwood. Amber first shot to reality TV fame in 2009, after she and then-boyfriend Gary Shirley appeared on 16 & Pregnant. They went on to star in the spinoff Teen Mom, but TV stardom wasn't all smooth sailing.

Over the course of her time on the series, viewers got a close look at Amber's tumultuous relationship with Gary. Unfortunately, after they split up, her relationship struggles only continued. She's since gone on to face numerous failed engagements, domestic violence arrests, and custody battles.

Here’s a look at the Teen Mom: The Next Chapter star's relationship history from then to now.

Amber began dating Gary Shirley when she was still a teenager in high school. The duo got pregnant in 2008, which landed them their spot on the show. They welcomed their baby girl, Leah Leann Shirley, in November of that same year.

Despite the fact that Gary proposed to Amber before their daughter was born, things ultimately didn’t work out. In Season 1 of Teen Mom, viewers witnessed Amber choke and slap Gary, leading Child Protective Services to investigate Amber. Eventually, the domestic issues between them got so bad that Amber lost custody of their daughter to Gary in 2011.

After more legal troubles that involved time in jail for probation violation and drug possession, Amber was ready to move on with her life. According to Us Weekly, in 2014, she got into a relationship with DJ Matt Baier, who she met via Twitter. Matt popped the question in November of that year and Amber said yes.

Unfortunately, Matt's past caught up with him and it wasn’t a great look. He admitted to having many children with multiple different women. In an attempt to save their relationship, the duo appeared on Marriage Boot Camp Reality Stars: Family Addition in 2017. Though Matt took the blame for his past actions, as well as cheating on Amber during their relationship, it wasn't enough for them to move forward. She called off their engagement while still filming the show.

While Marriage Boot Camp was wrapping up in 2017, Amber began dating Andrew Glennon, who worked as a cinematographer on the series. They got pregnant almost immediately and welcomed their son, James, in May of 2018.

By 2019, however, their relationship had crumbled. Amber got arrested once again for domestic battery, as well as recklessness with a deadly weapon, when she allegedly used a machete to break into a room where Andrew was holding their son. Andrew issued a restraining order against Amber and began the process of seeking full custody. After a long battle, Andrew was eventually granted primary custody in July of 2022.

Amber's next love interest, whom she met on social media, was a Belgium native by the name of Dimitri Garcia. Their relationship sparked at the beginning of 2020 and pressed on to 2021. Dimitri even appeared by Amber's side during Season 9 of Teen Mom OG. Though the two reportedly split at some point during 2021, The Sun reported in July 2023 that the two had rekindled their long-distance relationship as Amber was dealing with custody issues with Andrew Glennon. It's unclear what exactly happened next between Amber and Dimitri, but we know now that they didn't make it in the end.

According to Us Weekly, Amber met Gary Wayt on a dating app around September 2023. He lived near her Indianapolis home and was reportedly in his late 30s with no kids of his own, but was apparently "very family-oriented," according to the mag's source. And unlike some Amber's exes, he'd supposedly never seen Teen Mom. She later introduced him to her castmates via Zoom in an episode of Teen Mom: The Next Chapter that aired on June 6, 2024.

The two reportedly got engaged in either late May or early June 2024, but in mid June, Amber reported Gary as missing while they were in North Carolina for her brother's wedding, after she and Gary had an argument. (He was reported as located a few days later.) Later that month, they called off their engagement.