Amber Portwood

Amber Portwood/Facebook

Last August, life was going so well for Amber Portwood it felt like a good time to mend some fences.

Sure, she and Farrah Abraham had come this close to physical blows while filming a 2016 Teen Mom OG reunion special and exchanged countless curse words and pointed fingers throughout the two-minute scuffle, but, "I still love her to death," Portwood insisted during an appearance on E!'s Daily Pop. The only reason they were ever at odds, she explained, was because they both have a "very strong mind and strong opinions. Plus, she's crazy." Still, said Portwood, "I'm ready to let everything go."

Abraham was following a different script. Talking to E! News days later she rebuffed Portwood's olive branch. "In the same sentence she wants to be friends with me, she always says I'm crazy," says Abraham. So would she answer her call? "I believe she's blocked."

Okay, so not everything in Portwood's life has changed for the better. But the reality star has made an impressive turnaround since her days of chewing on fentanyl patches and lashing out at on-again, off-again love Gary Shirley—two habits that earned her a 17-month stint in Indiana's Rockville Correctional Facility. "I think I've changed a lot," the mom to 9-year-old Leah told E! News in 2015. Though if she's being honest, she can't truly be certain. "It's hard to think about my past because I can't remember half of it," she added of her drug-induced haze. "Now [I'm] living a sober life and trying to do good things. I'm trying to be normal."

For her, that means nurturing a months-long relationship with cinematographer Andrew Glennon, 33, and prepping for the May 13 arrival (one day before her 28th birthday!) of their son James Andrew. "I have a really calm, chill life," she recently told Us Weekly, "and I'm happy for the first time, genuinely."

Amber Portwood

MTV

This shiny, happy Portwood may have a hard time recognizing the pregnant 18-year-old who called Shirley "kind of an a--hole" as they filmed their audition tape for MTV's 16 and Pregnant. "I was so f--king mean," she admitted while watching the tape back on her 2015 Getting to Know special. "I was a bad kid, I really was."

The Anderson, Indiana teen and the certified nursing assistant three years her elder (he'd been in the same class as her older bro Shawn) had been dating for three years when her mom Tonya heard the network was casting for young mothers.

With the help of Tonya's camcorder they got to work. Though Portwood admits he didn't exactly put her best face forward. "I didn't think it was real," she conceded. "They didn't have a name for it yet because it was a pilot for it. So when I did it, I didn't take it serious. Like, I didn't do anything they wanted. I answered the questions, that was about it."

Her attitude didn't really improve when MTV decided to spin the success of their freshman series into a new docudrama. On the smash hit Teen Mom, viewers watched in horror as Portwood and Shirley's relatively harmless tiffs over money and Shirley's video game habit escalated.

Teen Mom, Amber Portwood

MTV

Even the most casual of fans is aware of that fight. The one that saw an enraged Portwood hit and punch Shirley, then attempt to push him on the stairs, all while then-1-year-old Leah toddled nearby.

Fueling her rage, she later admitted on Dr. Phil in 2013 was her fentanyl abuse. "I would eat the patch. It's, like, a three-day patch. It's very dangerous," she explained to Dr. Phil McGraw, adding, "Every time you see me on that show, I am high."

The behavior led to the most devastating of lows. Because of her on-camera brawl, Portwood was investigated by both local authorities and Child Protective Services (domestic violence in front of a child is a felony in Indiana) and eventually pled guilty to two felony counts of domestic battery in June 2011. But while she faced up to three years in prison, she was slapped with just two years' probation and mandatory anger management counseling.

That could have been the end, but the drama was just ratcheting up. While combing through her house, authorities uncovered opiates and she was charged with felony possession of a controlled substance—and violating probation—that December. She rang in 2012 in jail, but after pleading guilty, was told she could avoid a five-year prison sentence with court-ordered rehab.

Amber Portwood

E! Entertainment

Several months and a skipped drug test later, Portwood made the choice that stunned her fans: Rehab just wasn't for her; she'd take the prison sentence, thanks. 

Portwood credits that choice with saving her life. "In my situation, I felt in the program there were a lot of eyes on me. And it was very uncomfortable. I was not using my anti-psych medication even," she explained in a June 2012 ABC News jailhouse interview. "You know, I was very depressed, all alone, all bitter at everybody. I felt like that wasn't the life I wanted to live, I felt like I'd rather do my time, and get it over with, and make the best out of the situation that's been handed to me."

It wasn't necessarily the program that was the problem, per se, "It was the fact of being alone," she said. "It was personal. You know being alone, feeling like you're hopeless, you have nothing, feeling like an addict and you're never going to change, even though in your mind you're working so hard but every time you get to court it's not good enough."

At the depths of desperation, she had attempted suicide—twice—swallowing 30 tablets of Suboxone, a medication used to treat opiate addiction, in three days. "There's nothing lower than trying to kill yourself. That's why it's probably hard to understand why I did what I did," she said. "But when you mentally know that, you're not right. You're 22, and you tried to take your life twice. And you're 22, and you're still here, you don't want to mess that up."

Amber Portwood

Kamil Krzaczynski/INFphoto.com

True to her word, she applied herself during her year and a half in prison, earning her GED and participating in a substance abuse program. She also learned some lessons in the art of not taking the bait. "A lot of people know who I was and I would get women yelling across the yard some crazy things at me," she told E! News of her time in prison. "But I would say after five to six months, everything seemed normal…You just get used to it and you just learn to live in there. You want to do your time and you want to get out."

When she re-entered society, she'd learned it had moved on without her. Shirley, who she thought would remain committed during her sentence, was happily ensconced in a new romance with now-wife Kristina. Hurt, Portwood floundered her way through a series of relationships before finding love with former Montana radio DJ Matt Baier.

Amber Portwood, Matt Baier

Instagram

By the time Teen Mom returned in 2015, Portwood was sporting a sparkler from the Boston transplant and gushing about her forever love.

"Our relationship is completely different than what mine and Gary's was," she told E! News. "There's not really fighting or anything like that. It's not perfect, but we're so happy together. I never thought I could find another man that could make me feel love again."

Portwood was so enamored with the 46-year-old that she adopted a stand-by-your man attitude towards his somewhat alarming past. Sure, he'd fathered five (or was it six?) children with four different women. And, yes, his previous drug problems meant he'd been a less-than-ideal husband and father. However, reasoned Portwood, wasn't she, a former felon and drug addict, living proof that a person can change?

Amber Portwood, Matt Baier

Courtesy of DateBox

Still, years of playing defense wore on Portwood. There were cheating rumors and that time he embarrassed her on camera, hissing to a producer, "I will not marry her. I will not marry her now, ever!" after she rejected his plan to elope in Las Vegas. Perhaps the most egregious moment came when he offered costar Catelynn Lowell a Xanax from his stash—despite his insistence he'd been sober for years.

"Honestly, you just get to a point when you're done hearing things and you just start to not care in a relationship," Portwood explained on a "This Life #YouLive" episode with Dr. Drew Pinsky, "and I think that's what started happening to me and him. I started not to care anymore about the relationship like you should. I put a wall up so I wouldn't get hurt again pretty much."

By the time they signed up for a 2017 appearance on Marriage Bootcamp, their oft-delayed vows had been officially canceled and Portwood was touting their appearance on the reality show as Baier's last chance.

When he didn't rise to the occasion—after yet another relationship-ending fight, he skipped out on filming and jetted to Las Vegas—Portwood threw in her cards for good.

Baier insists he wasn't folding, simply escaping to Sin City "to get my head around the split," he explained to E! News. "Ultimately my hope was to get a place where Amber could come visit me and we could work on our issues. Obviously that didn't happen."

Andrew Glennon, Amber Portwood, MTV Video Music Awards 2017

Alberto E. Rodriguez/Getty Images

Instead, he gambled on a new romance, marrying mom of two Jennifer Conlon. And Portwood turned to Glennon, the 6-foot-7 teddy bear of a man who comforted her on the WE tv show's set.

Crew member Glennon admits to an instant infatuation. "The first day of filming, I was in the interview room with her and that's when I think I learned the most," he confessed to MTV producers on the Jan. 1 episode of Teen Mom OG. "From that point on, I'd try and place myself in the house where you were to hear more because I wanted to know even more."

Amber Portwood

MTV

When filming wrapped, his fascination kept rolling, so he reached out to Portwood to reconnect. A visit to Indiana turned into an extended stay for the Malibu native and, soon, as the newly minted couple were celebrating their love in Hawaii, Portwood discovered she was expecting.

"When I first found out, I was a little scared," she admitted to Us Weekly last year. "I just kind of sat down and thought about it and realized that it was a big step in my life and it was a good thing actually, and I was really happy within 30 minutes."

After all, she reasoned, this was something she wanted. With Baier, she used her borderline personality and bipolar disorder diagnosis as a reason why they couldn't have kids. "I can get pregnant, but it would mess up the fetus," she explained on an episode of the MTV hit. "If I do not have medication, I will not be normal. I would have...crazy mood swings.

Amber Portwood, Halloween 2017

Instagram

But with Glennon, she took a chance, weaning herself off her medication. "I needed to see where I was in my head," she explained to Us Weekly, "and it's a beautiful thing because I just feel better. I feel happier and not so depressed." (She's since resumed a medication "that's safe for pregnant women" she told the outlet.)

Being with Glennon, the man she credits with easing her post-Baier depression, has been her healthiest union to date. Any squabbling, say, over whether they should learn the gender of their baby, can be attributed to pregnancy hormones, says the founder of online boutique Forever Haute. And as they inch toward her May due date, they're proving to be a strong team.

Glennon has proved to be a doting partner, scrambling for ways to ease her nausea and helping to renovate her Indiana home with new carpet, flooring and a custom nursery, notes Portwood, now appearing with her mom on WE tv's Marriage Boot Camp: Reality Stars Family Edition. After James' arrival, they'll nest in a new spot, decamping to L.A. where Glennon will be producing a show from mid-June to late August. Then, she tells E! News, "We're going to figure it out."

Her wait-and-see attitude extends to marriage plans. While she says Glennon has dropped "little hints here and there," about a potential proposal they haven't discussed an engagement timeline. "Right now, we're happily leaving together," she says, "and seeing where everything goes."

So far, things are moving in the right direction.

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