'Teen Mom OG' Star Amber Portwood's Messy Relationship History

Highlights

• Amber Portwood has been in multiple tumultuous relationships, including with exes Matt Baier, Andrew Glennon, and Gary Wayt.
• Portwood's relationships have been marked by legal issues and drama, with her tumultuous personal life frequently making headlines.
• Despite Portwood's engagement to Gary Wayt, their relationship appears to have ended abruptly after Wayt was reported missing following a fight with Portwood.

Teen Mom OG star Amber Portwood is no stranger to controversy. She first appeared on our TV screens as a pregnant teenager on the MTV show, 16 And Pregnant, back in 2009. And since then, we’ve watched as Portwood struggled with motherhood, sobriety, legal woes and various romantic entanglements.

Since splitting with Gary Shirley, the father of her daughter, Leah, Portwood has been involved in a number of relationships with sometimes questionable men. She also lost custody of both of her children: Leah, 14, and James, 6.

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Most recently, Portwood made headlines after her now ex-fiance, Gary Wayt, went missing following a fight between the couple. Wayt’s missing person’s case was closed after police said he had been located three days after the initial report.

Here's a look back at Portwood’s relationship timelines.

5 Gary Shirley

Dated From: 2008-2011

Shirley and Portwood met as teenagers in Anderson, Indiana. After Portwood became pregnant at 18, the two were featured on the MTV docu-series that chronicled the lives and struggles of young parents. Shirley famously proposed to Portwood with a ring he purchased at Wal-Mart, but the two ultimately called off their engagement. Due to Portwood’s substance abuse and legal issues, Shirley was granted full custody of Leah in 2011. Since then, Shirley went on to marry Kristina Shirley and have another daughter, Emilee.

Portwood and Shirley have gone through their ups and downs as co-parents, but Shirley always made an effort to keep Portwood in Leah’s life. At times, Leah has been reluctant to form a healthier bond with her mother, since Portwood has been in and out of her daughter's life. Leah has seemingly lived a stable life with her father and stepfather. Her relationship with her mother continues to be a work in progress.

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4 Matt Baier

Dated From: 2014-2017

Portwood debuted her new boyfriend, Matt Baier, in 2014. Baier was 19 years older than Portwood. The two famously met on social media, with news that Baier had allegedly reached out to multiple stars of the docu-series putting a bit of a damper on their romance. Baier appeared on episodes of Teen Mom OG while allegations about Baier’s personal life, including the fact that he fathered multiple children unbeknownst to Portwood, coming to light.

Their relationship was tumultuous, with cameras catching many of their disagreements. They became engaged in 2015 before calling it off in 2017 after appearing on Marriage Boot Camp Reality Stars: Family Edition.

3 Andrew Glennon

Dated From: 2017-2019

Portwood rebounded from her failed romance with Baier with Andrew Glennon, a production member on Marriage Boot Camp. Glennon also appeared on the MTV show as Portwood's partner. But, in true Portwood fashion, the relationship was anything but stable.

The couple welcomed a son, James, in 2018, but by 2019, Portwood was in hot water with the law again following a terrifying incident where Glennon accused Portwood of domestic assault after she reportedly chased him with a machete while he held their son. The couple's relationship ended the same year and, in 2022, Glennon was given full custody of their son.

During an appearance on Teen Mom OG in 2020, Glennon explained to producers that he chose to resume filming so that he could tell his side of the story.

"I was never given any kind of outlet to share the other side of the story," he said. "We all make mistakes — I’ve made mistakes. I think in this whole process, all I wanted was ownership, honesty — mental illness is real."

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At the time, Portwood told US Weekly that despite her struggles, her children remain her priority, saying, "I’ve worked so hard to better myself and improve my relationships with my children. 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. I’ll never stop fighting for my children who I love more than anything.”

2 Dimitri Garcia

Dated From: 2020-2021

Following in the footsteps of Portwood's previous paramours, Dimitri Garcia also appeared on the MTV show as the long-distance partner of Portwood in 2021. Garcia, who lives in Belgium, appeared mostly through video chatting during his time on TV. However, Portwood's international romance was not meant to be. The couple split in 2021 amidst her complaints that Garcia was controlling.

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1 Gary Wayt

Dated: 2024

Fans barely got a glimpse of Portwood's latest beau, Gary Wayt (affectionately known as Gary 2.0), on the latest season of Teen Mom: The Next Chapter. Portwood gushed about her latest relationship with Wayte, showing photos of her new boyfriend to her daughter and ex, Shirley. Their engagement was announced in June of 2024. However, days later, on June 9, Wayte was reported missing in North Carolina following a fight between the couple. The couple had just attended the wedding of Portwood's brother, Shawn, but reportedly argued following the event. Wayte reportedly left the cabin he and Portwood had rented without taking his cell phone.

On June 11, according to US Weekly, Portwood appeared on a podcast to plea for his safe return. "This is a huge deal, his parents, everybody is very worried. I am worried. There was not a big blowout fight or anything like that. He is a missing person right now.”

By June 14, police announced Wayte had been found and the missing person's case was closed. While the couple haven't officially announced their split, it seems imminent given the whole missing person's case.

Teen Mom

Teen Mom (retitled Teen Mom OG) is a reality-drama TV series created for MTV that follows a growing cast of several young mothers who experience teenage pregnancy and must navigate the challenges of having a baby at a young age. The show follows their growth while focusing on the drama and complicated family dynamics that emerge.

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