Teen Mom OG’s Amber Portwood and Her Daughter Leah’s Ups and Downs Through the Years

Credit: Courtesy of Amber Portwood/Instagram

Teen Mom OG's Amber Portwood and Her Daughter Leah's Ups and Downs Through the Years

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." [jwplayer gONHPZGL-zhNYySv2] 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. [podcast_block]

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December 2015

"I hope he’s not saying s--t to her [about me]," Portwood said of Shirley during a Teen Mom OG episode. "If I ever find out he’s saying s--t to her, it’s on.”

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March 2018

"She’s getting older and it’s becoming to the point where she kind of decides when she wants to go back and forth and what she wants to do, which is a great thing," Portwood told Us. "Some weekends she wants to go and spend the night with her friends or do something else. I mean, she’s a kid so I can’t really get mad at that. But I do miss her a lot and I do explain to her that, even though she’s young, ‘Mommy still wants to see you more,’ and things like that. She understands, but she’s a kid. … As long as she knows that I love her and that we spend time together … that’s really all that matters. As long as she’s happy.”

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August 2019

"[Leah] knows a lot of what’s going on,” Anderson said of Portwood's arrest. “I think the only thing she’s said to me is, ‘If Mommy goes back to prison, what happens to James? Will James be taken away from me as well?’ I don’t have those answers.”

Credit: Courtesy of Amber Portwood/Instagram

November 2019

Prior to taking an Instagram hiatus, Portwood celebrated her daughter's 11th birthday, writing, "What an absolute beautiful day with family and this beautiful Birthday girl!!"

Credit: AMI/MEGA; Courtesy of Kristina Shirley/Instagram

March 2021

"I try to invest time with Leah all the time," Portwood said in an Instagram Live video. "It's all I ever do."

Credit: Courtesy of Amber Portwood/Instagram

April 2021

"I know you are going through a lot and there are many things I need to do to make things right," she captioned an Instagram selfie. "However, I will always love you, my beautiful daughter. Love you and Happy Easter."

Credit: Courtesy of Kristina Shirley/Instagram

September 2021

Portwood said during a Teen Mom OG episode that she hasn't seen Leah in a "long time," explaining, "Leah and I are still struggling with our relationship. My relationship with Leah has changed a lot. I haven't heard back from Gary or Leah if I can see her on Easter. I feel very stressed right now. A little sad. … All I do is text Leah all the time. I don't get anything back. Never. Not anymore.”

Credit: MTV

September 2021

The reality star cried over her relationship with her daughter on the show, saying, "It truly breaks my heart that Leah and I are drifting apart. I really think if I could go to therapy with Leah, it would bring us closer together. ... We've already talked about therapy for Leah, but Gary wasn't for it at all. Therapy is a good thing to get you and your mother back together and having that mediator can get you to open up and understand a bit. I think she'll be happier in life to understand a bit more of what the past was and how I am today. It's OK to have a mom that has been through these things. You shouldn't be ashamed about it. Therapy is something that needs to happen."

Credit: Courtesy of Amber Portwood/Instagram

September 2021

Portwood told producers that she hadn't been in contact with Leah in "a couple of months," explaining, "I can’t sit here and have her think things that aren’t true about me 'cause I am her mother. ... How many times do I need to apologize?"

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October 2021

Portwood reflected on an "awkward" reunion with Leah. "But I think with time, it will be a little better," she said. "I just try to explain to her, 'I've been there before, but today my mom is my best friend. You can hate me right now. That's OK. I understand.'"

Credit: Courtesy of Amber Portwood/Instagram

November 2021

Leah was “off” during her visit with Portwood in a Teen Mom OG episode, the reality star told one of the producers. “I already thought that was going to be that way," she explained. "The only thing that bothered me with Leah is she was kind of getting a little snappy at a point. Don't talk to me like that. Other than that, I was perfectly fine with everything. It felt good. I mean, it's been a little while since the last time I went there. I miss her, like, a lot. I miss little text messages, phone calls, Snapchat. The point is being there. Just showing up to her was a big deal. All I need to do now is just keep showing up no matter what she says and not push but just be present. Nothing's perfect."

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January 2022

Portwood's visits with Leah were going "a lot better," the So You're Crazy Too? author exclusively told Us, adding, "I can’t speak for Leah, but then we’re around each other now, it’s night and day. It’s just beautiful."

Credit: MTV

January 2022

Portwood admitted during Teen Mom: Family Reunion that she used her depression as “an excuse to not do anything” for her daughter and was trying to take “accountability” for her previous actions. “There's no excuse,” she said. “I was trying to keep Leah away from all of the bad s--t back in the day. I was trying to do this, trying to do that. And then I was like, 'Well, I could have went over there still though. Why didn't I go over there?' Like, 'I could have still did this, I could have still picked her up.’”

Credit: MTV

January 2022

Portwood admitted during Teen Mom: Family Reunion that she used her depression as “an excuse to not do anything” for her daughter and was trying to take “accountability” for her previous actions. “There's no excuse,” she said. “I was trying to keep Leah away from all of the bad s--t back in the day. I was trying to do this, trying to do that. And then I was like, 'Well, I could have went over there still though. Why didn't I go over there?' Like, 'I could have still did this, I could have still picked her up.’”

Credit: Courtesy of Amber Portwood/Instagram

September 2022

During the series premiere of Teen Mom: The Next Chapter, Amber attended Leah's 13th birthday celebration. After the drama-free party, the teenager told her father that she wanted to smooth things over with her mother.

"I want us to be friendly together and not have any issues or anything. I don't want to have any tension or for it to be awkward with her,” she said. "I feel like we're taking a big step. It is still awkward because I don't know what to say most of the time, but we're taking a big step into having something."

Meanwhile, Amber told MTV cameras she was "being patient" and "doing my best to be present for [Leah] while respecting her boundaries.”

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February 2023

During an episode of Teen Mom Family Reunion, Portwood reflected on her past parenting choices when it came to Leah.

"I knew that I was not doing everything that I could with Leah. Now, so much has changed," the reality star shared with Dr. Cheyenne Bryant — a.k.a. Coach B — at the time. “Back in the day I thought staying away was the best thing to do for Leah and it actually just completely backfired a couple years later."

To help heal her wounds, Coach B had Portwood plant seeds as a symbolic gesture of growth.

“The first seed that I’m planting is for the love the Leah did not receive from me a long time ago because I thought that she would be better off without me because I thought that I would just hurt her future and I want this to grow so that she will know that I never gave up on her," Portwood cried.

“There is nothing that I will ever be able to do to fix any of that stuff but I just have to keep going," she added in a confessional.