Amber Portwood’s fraught relationship with daughter Leah has been documented on Teen Mom over the years.
Portwood gave birth to her baby girl in 2008 with then-boyfriend Gary Shirley. The former couple split three years later, with Shirley going on to wed Kristina Anderson, with whom he shares daughter Emilee.
As for Portwood, the MTV personality is also the mother of son James with Andrew Glennon, whom she lost custody of in 2022 following a three-year court battle over a 2019 domestic violence incident.
Her relationship with Leah, meanwhile, has been strained over the years due to Portwood’s substance abuse issues, mental health problems and previous prison time.
“I feel like I’m never going to win,” Portwood said during a September 2021 episode of the MTV show, claiming that her daughter 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:
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.”
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.”
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.”
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!!"
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."
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."
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
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."
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?"
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.'"
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."
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."
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.’”
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.’”