Amber Portwood’s Tumultuous Love Life: A Deep Dive into Her Relationships and Dating History

Since her debut on MTV’s ‘16 and Pregnant’ in 2009, Amber Portwood has navigated a highly public and often tumultuous romantic life. The ‘Teen Mom OG’ star, now 31, has lived under the constant scrutiny of fans and media, with her personal journey — including her relationships — unfolding on national television. While she has been officially engaged twice, her five most significant relationships have each profoundly shaped her life, contributing to her growth, challenges, and understanding of love and family. This comprehensive overview explores Amber Portwood’s major romantic connections, detailing the key moments, the public’s reaction, and the lasting impact each partner has had on her journey.

From the early days of young motherhood to navigating complex co-parenting dynamics and personal struggles, Amber’s relationships have consistently been a central theme in her narrative. Her openness about her struggles, including battles with mental health and legal issues, has made her story relatable yet incredibly dramatic. Each chapter of her romantic history offers insights into the pressures of fame, the complexities of love, and her enduring quest for stability and happiness.

Gary Shirley

Gary Shirley, now 35, holds a uniquely significant place in Amber Portwood’s history, not only as her first love interest on ‘16 and Pregnant’ but also as the father of her eldest daughter, Leah Leann Shirley. Their relationship began in 2008, leading to Amber’s pregnancy and Leah’s birth on November 12 of that year. The couple’s journey into parenthood, marked by their youth and the glare of reality television, was fraught with challenges. They were briefly engaged, a hopeful but ultimately short-lived chapter, as their tumultuous dynamic proved difficult to sustain.

The relationship’s volatility reached a critical point in September 2010, when MTV aired shocking footage depicting Amber assaulting Gary. This incident, which included Amber punching, choking, and kicking Gary, resulted in injuries and ignited a major public and legal firestorm. Amber faced three felony charges of domestic violence, leading to a period of intense legal battles and public scrutiny. Their separation officially occurred in 2011, with Gary being awarded full custody of Leah, a decision that profoundly impacted Amber and set the stage for years of complex co-parenting.

Despite their romantic separation and past conflicts, the co-parenting journey for Amber and Gary has evolved remarkably over the years. This evolution was not without its struggles, particularly as Gary moved on to marry Kristina Shirley and welcomed another daughter, Emilee Grace Shirley. Gary also embarked on a career as a police officer, establishing a stable family life that sometimes highlighted the ongoing challenges Amber faced. Initially, peaceful co-parenting seemed an insurmountable task, often strained by their personal history and Amber’s continued struggles. However, through perseverance and a shared commitment to Leah’s well-being, they have managed to forge a more respectful and even supportive relationship.

A testament to their improved dynamic came in March 2022, when Amber publicly expressed her support for Gary after he underwent bilateral carpal tunnel surgery. She shared a heartfelt message on Instagram on March 4, accompanied by a photo of neon angel wings: “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. 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!” This public display of solidarity underscored the deep bonds that still exist within their blended family, demonstrating a maturity and mutual respect that few might have predicted during their early, tumultuous years on television. Their journey from volatile young lovers to effective co-parents and supportive family members is one of the most compelling narratives within the ‘Teen Mom’ franchise.

Matt Baier

Following her separation from Gary Shirley, Amber Portwood ventured into a new relationship chapter, notably meeting DJ Matt Baier through social media, specifically Twitter. This connection quickly developed into a serious relationship, despite an almost two-decade age difference between them. When they began dating in 2014, Amber was in her mid-20s, while Matt was in his mid-forties, a dynamic that immediately garnered significant public attention and raised eyebrows among fans and her co-stars alike. The speed at which their relationship progressed was also a point of discussion; they became engaged in 2015, signaling a rapid progression towards what seemed like a permanent commitment.

However, the relationship with Matt Baier was plagued by numerous controversies and red flags from its inception. Public reports and investigations revealed troubling aspects of Matt’s past, including allegations of having multiple children he did not support, financial issues, and a history of pursuing other reality television personalities. These revelations often played out on ‘Teen Mom OG’, causing significant strain on Amber and Matt’s relationship and eroding public trust. Despite these challenges, Amber often defended Matt, hoping to build a stable future with him.

Their tumultuous journey culminated in their participation in ‘Marriage Boot Camp’ in 2017, a last-ditch effort to salvage their relationship ahead of a planned wedding that October. It was during the filming of this show that the full extent of their issues became undeniable. Revelations of Matt’s infidelity surfaced, confirming Amber’s suspicions and deeply betraying her trust. The experience on ‘Marriage Boot Camp’ served as the catalyst for their final split, which occurred in June 2017. The breakup was widely publicized, marking another high-profile romantic failure for Amber.

In the aftermath of their separation, Matt Baier publicly took responsibility for the demise of their relationship. In an interview with E! News in August 2017, he expressed remorse, stating, “I’m trying to do a lot of work on myself because I realize now the downfall of our relationship was my fault. When you’re thrust into the spotlight like that, it can affect you. My mistake was taking our relationship for granted.” This statement, while acknowledging his role, did little to soothe the disappointment of fans who had watched Amber endure significant emotional distress during their time together. The relationship with Matt Baier remains one of the most scrutinized and controversial chapters in Amber Portwood’s dating history, underscoring the complexities and pitfalls of seeking love in the public eye.

Andrew Glennon

In the summer of 2017, shortly after her split from Matt Baier, Amber Portwood met Andrew Glennon, a cinematographer from Southern California, now 37. Their relationship progressed rapidly, leading to Amber becoming pregnant with her second child. Their son, James Andrew Glennon, was born on May 8, 2018. During the early stages of their relationship, Amber often spoke glowingly about Andrew, describing him as her “soulmate” and a “beautiful person” in an interview with Us Weekly in May 2019. This period seemed to mark a hopeful new beginning for Amber, who appeared to find a sense of stability and happiness with Andrew.

However, this promising chapter soon took a dark turn. On July 4, 2019, an argument between Amber and Andrew concerning fireworks escalated into a domestic dispute that once again brought Amber into legal trouble. The incident led to her arrest and, alarmingly, three new felony charges. This arrest was a stark reminder of her past struggles with anger and domestic violence, echoing the earlier incident with Gary Shirley. The public reaction was one of dismay and concern, as many hoped Amber had moved past such destructive behaviors. The legal proceedings that followed were intense and emotionally draining for both parties.

Amber eventually accepted a plea deal in the case, but the repercussions extended far beyond the courtroom. The incident triggered a bitter and protracted custody battle over their son, James. Andrew Glennon sought and was ultimately awarded primary physical custody of James, a devastating blow to Amber. The loss of primary custody for her second child was a profound personal setback, highlighting the ongoing challenges she faced in managing her mental health and maintaining stable relationships. This outcome forced Amber to confront her actions and their consequences on a deeply personal level, further intensifying her journey of self-reflection and personal growth.

The relationship with Andrew Glennon, despite starting with such high hopes and the joy of welcoming a new child, ultimately ended in heartache and further legal complications. It underscored the persistent difficulties Amber faced in maintaining healthy romantic partnerships and managing her emotions under pressure. The public scrutiny only amplified the pain, as fans witnessed another cycle of promising beginnings turning into distressing endings, particularly when children were involved. This period of her life deeply impacted her public image and her personal well-being, pushing her to continue seeking therapy and focusing on her mental health journey.

Dmitri Garcia

Following the very public and challenging split from Andrew Glennon, Amber Portwood embarked on a new, notably more private relationship with Belgian native Dmitri Garcia. The two were first linked in January 2021, and their romance unfolded largely away from the intense glare of the cameras, a significant departure from Amber’s previous high-profile relationships. This period suggested a desire for a calmer, less dramatized personal life, especially after the tumultuous events surrounding her custody battle with Andrew.

Amber and Dmitri maintained a relatively low profile, which contrasted sharply with the extensive coverage of her past relationships on ‘Teen Mom OG’. This privacy allowed for a different dynamic, where the relationship’s progression was not immediately subject to public opinion or reality television narratives. However, by October 2021, sources indicated that Amber and Dmitri were no longer together as a couple. Despite the romantic separation, a source close to HollywoodLife revealed that the two maintained contact, suggesting a friendly or amicable parting. “Amber is still talking to Dimitri but he’s overseas right now,” the source stated. “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.”

This statement provided insight into the nature of their bond and, more importantly, highlighted Amber’s renewed focus on personal development. The relationship with Dmitri, while not leading to a long-term commitment, seemed to mark a period of introspection and a conscious effort to prioritize her well-being and growth. Unlike previous relationships that often involved dramatic public fallouts, the narrative around Dmitri suggested a more mature approach to dating and personal connections. It underscored a shift in Amber’s priorities, moving away from seeking immediate romantic fulfillment towards a journey of self-improvement and stability.

The possibility of a future reunion, as hinted by the source, suggests that there was no significant animosity or irreparable damage to their connection. Instead, the geographical distance and Amber’s commitment to her personal journey appear to be the primary factors in their current status. Dmitri Garcia represents a different kind of relationship chapter for Amber Portwood—one characterized by discretion, a focus on personal boundaries, and a continued emphasis on her ongoing path toward emotional and psychological health, even amidst the ever-present challenges of life in the public eye.

Amber Portwood’s journey through multiple high-profile relationships since her introduction on ‘Teen Mom’ has been a compelling and often challenging narrative. From her tumultuous beginnings with Gary Shirley, through the controversial chapter with Matt Baier, to the devastating custody battle with Andrew Glennon, and finally to her more private connection with Dmitri Garcia, each relationship has served as a significant milestone in her personal evolution. Her story is a testament to the complexities of growing up under intense public scrutiny, navigating personal struggles, and striving for stability as a mother and an individual.

While her romantic life has been marked by dramatic highs and lows, Amber’s narrative also reflects a persistent quest for self-improvement and mental well-being. The public has witnessed her raw emotions, her struggles with domestic violence charges, and her efforts to manage her mental health. Through therapy, personal reflection, and a steadfast dedication to her children, Leah and James, Amber continues to work towards building a more peaceful and fulfilling life. Her journey is far from over, but her experiences in these significant relationships have undoubtedly shaped the resilient, albeit imperfect, woman she is today, constantly striving for a healthier future for herself and her family.