Amber Portwood Reflects on 'Awkward' Reunion With Daughter Leah

‘Teen Mom OG’ star Amber Portwood shares her daughter, Leah, with ex-fiance Gary Shirley — details on their relationship

Highs and lows. Amber Portwood’s fraught relationship with daughter Leah has been documented on Teen Mom OG over the years.

The Indiana native gave birth to her baby girl in 2008 with then-boyfriend Gary Shirley. The former couple split three years later, and the police officer went on to wed Kristina Anderson in 2015 in Michigan. They share daughter Emilee.

As for Portwood, the Never Too Late author is also the mother of son James with Andrew Glennon. The exes have been coparenting their baby boy since her July 2019 domestic battery arrest and their subsequent breakup. The California native has primary physical custody, sharing joint legal custody with Portwood.

The 16 and Pregnant alum exclusively told Us Weekly in March 2020 that she saw James “fairly a lot,” saying, “I am trying to coparent the best way that I can. I get a lot of people tell[ing] me after my days with him: ‘I can tell that you saw James today because you just have that smile on your face.’ When I hear that, I’m like, ‘Yeah. It’s just the truth.’ Just something in my heart told me, ‘Amber, you’re going to be back with your son one day. And it doesn’t matter if it’s one day a week, two days a week, three days a week, four days a week. It was hard work in the beginning … I just kept trying to focus on myself and my son and my family and I got him back as much as I can right now.”

While Portwood felt “great” about her relationship with her youngest child at the time, she and Leah struggled more.

“I feel like I’m never going to win,” the Forever Haute creator said during a September 2021 episode of the MTV show, explaining that the preteen was “acting weird” and had “turned” on her. “I wanted us to have a great coparenting family that I thought we had until it became weird.”

Portwood added at the time: “This is not [Leah]. She does not ignore me like this. Even if I take responsibility for every single wrongdoing I’ve ever done, it just feels like it’s never enough.”

Keep scrolling to see the MTV personality’s evolving relationship with Leah over the years, from a birthday celebration in November 2019 to an “awkward” visit in October 2021.