Amber Portwood’s Dating History & Past Relationships with Ex-Boyfriends

Amber Portwood

Instagram "Teen Mom OG" star Amber Portwood has been engaged twice and introduced several boyfriends on the MTV reality show.

Teen Mom OG star Amber Portwood has been engaged twice and introduced several boyfriends on the MTV reality show. Her new beau, Dimitri Garcia, traveled from Belgium to be with her in Indiana, but the mother-of-two isn’t sure if she’s ready to trust him. Last week, she made him take a lie detector test to prove his intentions with her were pure. During a therapy session on Tuesday’s episode, Portwood reveals shes struggled with her relationships throughout her life.


Gary Shirley Was Portwood’s First Fiance

Portwood’s first serious boyfriend was Gary Shirley, who proposed to her while she was still pregnant. The couple shares 11-year-old daughter Leah together and starred on 16 and Pregnant during its first season. They had a volatile relationship together, which included Portwood physically assaulting Shirley while MTV cameras were rolling in August 2009.

Leah, who was 1 at the time, was present at the time of the assault. Portwood pleaded guilty to two felony charges of domestic battery and stayed behind bars for nearly two years, the Indy Star reported.

They struggled with their relationship throughout the years as they tried to co-parent Leah, but recently Shirley and his wife, Kristina Anderson, have become one of Portwood’s biggest supporters. Shirley has helped take Portwood to therapy sessions and invited her over to family dinners.


Portwood Nearly Married Matt Baier

According to Who’s Dated Who, Portwood and ex-fiance Matt Baier dated from 2013 to 2016. The couple met on Twitter and had an on-again, off-again relationship. Baier tried to get Portwood to agree to elope in Las Vegas, but the star ultimately backed out.

Throughout their relationship viewers accused Portwood and Baier of showing abusive behavior toward each other. In a 2018 episode of Marriage Boot Camp, Baier took a polygraph test after Portwood claimed Baier allegedly hit her.

“You’ve never had my back,” Portwood said at the time, as noted by People magazine. “You’re just a childish person. You can act that way you want, try to depict me as the liar. I would like my exes to come out and say amber’s never put a hand on me.”

They both went their separate ways after the show, with Portwood dating Andrew Glennon and Baier marrying Jennifer Kathleen Conlon. The split wasn’t amicable, but Baier doesn’t harbor any ill feelings toward his ex.

“We spent three years building a life together and they were the three happiest years of my life,” Baier told E! News at the time. “I wouldn’t trade them for anything.”


Portwood Allegedly Attacked Glennon With a Machete

When Portwood’s son James with Glennon was 1, the two got into a fight in July of 2019 over fireworks. The argument escalated, with Portwood allegedly using a machete to get through a door Glennon was behind while he was holding the baby.

Portwood pleaded guilty two felony charges of domestic battery and intimidation in October. She was sentenced to more than 900 days of probation, the Indy Star wrote.

Since Portwood has talked about the incident on Teen Mom OG, producers wanted to give Glennon the chance to state his side. But Glennon wanted equal pay. None of the partners on Teen Mom–except to original dads like Shirley and Tyler Baltierra–get paid the same as the main mothers, The Ashely wrote. With substantially less pay, Glennon wasn’t willing to appear on camera and quit the MTV reality show.

“The ONLY way I would consider continuing the same show with the person who inflicted the pain, who inflicted such pain and abuse upon James and I, would be if we were paid the same as our abuser,” Glennon said in an exclusive statement to The Ashley. “Seems only fair. Anything else would be wrong on so many levels and an insult. That was my price for continuing to be their punching bag.”

Nearly six months after her split from Glennon, Portwood began to date Garcia. It’s unclear if they’re still together, since Portwood went on a social media hiatus in November.

I have to be done with this for myself to evolve and move forward. This is not worth me or my family’s stress. We are moving on while I am getting the help I need to better myself and live a healthy life. In the end it is all irrelevant because we are all human and make mistakes. Own up to them and try to become the person you want to be truly. Sending love to all the beautiful souls trying for a better life.

To find out what happens next, don’t miss Teen Mom OG when it airs Tuesdays at 8 p.m. ET on MTV.

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