Amber Portwood’s Boyfriends: Everything To Know About ‘Teen Mom’ Star’s Dating History

Amber Portwood has been engaged twice and had several high-profile relationships since she began appearing on 'Teen Mom' in 2009!

Reading Time: 4 minutes
Amber Portwood Gary Shirley
View gallery
Image Credit: SplashNews

Amber Portwood, 31, has been through a series of very public relationships since she first appeared on MTV’s enormously successful reality series 16 and Pregnant in 2009.  The Teen Mom OG star has lived her life in the public eye since then, gaining fan and media attention for her sometimes-volatile personal life. And while she was only engaged twice, (to baby daddy Gary Shirley, now 35, and boyfriend Matt Baier, now 50), it’s clear that each of her five relationships have shaped her current life in different ways.  Here’s everything you need to know about Amber’s five serious relationships.

Gary Shirley

Amber Portwood and Gary Shirley
Amber Portwood is seen walking with Gary Shirley.

Gary was Amber’s first, and is still perhaps the most recognizable, of her relationships since becoming a teen mom. Amber became pregnant with Gary in 2008, and by November 12 of that year, the couple had become parents to daughter Leah Leann Shirley. They were briefly engaged, but ultimately separated in 2011, with Gary getting full custody. The separation followed a shocking incident of domestic violence aired on MTV in September 2010, showing Amber assaulting Gary by punching, choking, and kicking him, which resulted in injuries. A major investigation followed, and Amber was charged with three counts of domestic violence against Gary. The duo struggled to peacefully co-parent Leah, with Gary marrying Kristina Shirley, having daughter Emilee Grace Shirley, and becoming a police officer, while Amber went on to date a series of other men.

Over the years, all three have become supportive of each other, with Amber sending out supportive messages in March 2022 after Gary underwent surgery for carpel tunnel syndrome. “Please send all of your love positivity and encouraging words for me, my family, and especially @itsgarytime @kristina_shirley3 for his recovery from bilateral carpal tunnel surgery,” she wrote via Instagram on March 4, alongside a photo of neon angel wings. “Let’s send them all the light and love for the ease of any pain and pray that he can get back to the things he loves most super soon!”

Matt Baier

Amber Portwood and Matt Baier
Amber Portwood and Matt Baier in Los Angeles. (SplashNews)

Amber took to social media for her next relationship, meeting DJ Matt Baier through Twitter. Matt and Amber reached across an enormous age difference to find common ground, as Matt is nearly two decades older than the Teen Mom OG star. When the two started dating in 2014, Amber was only in her mid-20s, and Matt was in his mid-forties. They were engaged in 2015 but ultimately broke up while in the middle of filming Marriage Boot Camp in 2017, their last attempt to make it work before a planned wedding date that October. It didn’t help that Amber discovered he’d cheated on her during the relationship. Matt took the blame for the June 2017 split and expressed regret. “I’m trying to do a lot of work on myself because I realize now the downfall of our relationship was my fault,” he told E! News in August 2017. “When you’re thrust into the spotlight like that, it can affect you. My mistake was taking our relationship for granted.”

Andrew Glennon

Amber Portwood and Andrew Glennon
Amber Portwood and Andrew Glennon arrive at the MTV VMA Awards on August 27, 2017 in Los Angeles. (SplashNews)

Amber moved on to Andrew Glennon, now 37, a Southern California cinematographer, in the summer of 2017, and it wasn’t long before she became pregnant with her second child. Their son, James Andrew Glennon arrived on May 8, 2018. She gushed over their connection, telling Us Weekly in May 2019 that he was her “soulmate” and calling him a “beautiful person,” but it wasn’t long before Amber ran into trouble with the law again — a fight ove fireworks between the two on July 4, 2019, resulted in her arrest and again, three felony charges against her. She accepted a plea deal in the case, but after a nasty custody battle, Andrew was awarded primary physical custody of little James.

Dmitri Garcia

Amber was next seen cozying up to Belgium native Dmitri Garcia in January of 2021, following the very public split with Andrew. The two kept a low profile, but a source told HollywoodLife in October 2021 that the couple are no longer together but keep in contact. “Amber is still talking to Dimitri but he’s overseas right now,” the source said. “If he comes back to the U.S., it could happen that they get back together. That’s the only guy she’s speaking with. They are still close, but Amber‘s been super focused on working on her own growth.”

More From Our Partners