Amber Portwood: "Messy" Relationship With Andrew Glennon Exposed!

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When Amber Portwood first met Andrew Glennon, she was still engaged to Matt Baier.

One month after the couple began dating, Amber got pregnant with her second child.

Shortly thereafter, Glennon abandoned his life in LA in order to move to Indiana to be with Amber.

Needless to say, these two don't believe in wasting time, but just because their relationship has been moving quickly, that doesn't mean either of them are actually happy with their circumstances.

In fact, those who know their situation best say Amber and Andrew's relationship is "messy" at best and downright disastrous at worst...

1. The Not-So-Happy Couple

The Not-So-Happy Couple
Amber and Andrew have done a stellar job of keeping up appearances on social media, but Teen Mom OG fans know their short relationship has already experienced its fair share of rough patches.

2. An Inauspicious Start

An Inauspicious Start
Andrew was a producer on Marriage Boot Camp, and he apparently hit it off with Amber during her time on the show. When Portwood's then-fiance, Matt Baier, took off for Vegas, Amber and Andrew began a relationship.

3. Red Flags Everywhere

Red Flags Everywhere
Fans were hopeful that after a decade of strife, Amber might finally find some stability in her relationship wth Andrew. Unfortunately, they began their relationship just days after she broke off her engagement with another guy, and that wasn't the only cause for concern.

4. A Sketchy Past

A Sketchy Past
It wasn't long before media outlets began unearthing evidence of Andrew's seriously troubling past. Suddenly, fans went from hopeful about the future of her new relationship to deeply concerned for her safety.

5. Cause For Concern

Cause For Concern
Two of Andrew's exes have obtained orders of protection against the former television producer. One woman claimed that he stalked and harassed her when she broke up with him after just a few weeks of dating.

6. History Repeats Itself...

History Repeats Itself...
Now, one person who was there from the very start of Andrew and Amber's romance says it looks as though both parties are repeating the destructive mistakes that doomed their previous relationships...

7. Dr. Ish Sounds Off

Dr. Ish Sounds Off
In the latest issue of In Touch Weekly, Marriage Boot Camp therapist Dr. Ish Major shared his thoughts on Amber and Andrew's relationship. And it seems he's not too optimistic about the couple's future.

8. A Rocky Beginning

A Rocky Beginning
It seems Dr. Ish believes that Amber and Andrew would have to put in serious work in order to make up for the impetuous way their relationship began - and they're simply not doing it. “The issues with [her new relationship] is the impulsivity of it,” Dr. Ish told the tabloid.

9. A Messy Situation

A Messy Situation
"You are in a program designed to get you some closure and move forward in your life, in wherever direction that takes you — but while you’re in the program, the guy you came with doesn’t work out, so you end up with another guy, and you ended up getting pregnant — it’s a mess," Ish continued.

10. Throwing Shade?

Throwing Shade?
Many have believe Dr. Major meant to suggest that Andrew had overstepped his professional boundaries in becoming involved in a relationship with Amber. But it takes two to tango, and Portwood never seemed to have any doubts about Glennon.

11. No Angel

No Angel
Amber has a rather checkered past of her own, which includes multiple arrests, assault charges, and even some time behind bars. Major believes the combination of the two strong, impulsive personalities might result in a powder-keg situation.

12. Know Thyself

Know Thyself
“I think she should’ve stayed single longer and really gotten to know herself and get over someone before getting with someone else — because that’s how you do it, man,” Ish said. “The correct way. You don’t need someone to make you feel like you’re living.” Sounds like Dr. Ish hasn't watched a whole lot of Teen Mom OG.

13. Another Reason to Be Worried

Another Reason to Be Worried
Amber has struggled with addiction throughout her life, and she recently revealed that she was frequently less than sober on the Marriage Boot Camp set.

14. Mixing Meds

Mixing Meds
“I was heavily drinking on top of my bipolar and borderline medication,” Amber tweeted of her time on the show. “Obviously something you shouldn’t do with medications like that. However, it happened and I went through hard times in order to be truly happy finally.”

15. Quick to Forgive ... Herself

Quick to Forgive ... Herself
Amber basically reveals and justifies her behavior in the same breath with that tweet. It's the sort of behavior that's always infuriated fans, and many believe her delusional narcissism has been with her since childhood, forever supported and defended by the most important man in her life...

16. Shawn to the Rescue

Shawn to the Rescue
Shawn Portwood is Amber's beloved brother. And many Teen Mom OG fans consider him to be her number one enabler.

17. The Containment Factor

The Containment Factor
"When I said that Andrew ‘contains her’ in a sense, I mean it,” Shawn said in a recent interview with The Ashley's Reality Roundup. “Her mood and her behavior has chilled out a lot since they’ve been together. I have never shied away from the fact that I believe she moves really quickly, but I think this is one move that she made that has benefited her health and her family situation.”

18. Dr. Ish Doesn't Know Ish

Dr. Ish Doesn't Know Ish
Shawn also stated that he has zero respect for Dr. Major's professional opinion: "I am sure from a medical standpoint he probably has some reason to believe what he said but I do not think that it was correct for him to say that,” Shawn told The Ashley. “He only got 10 days to know my sister. I have known her for 27 years.

19. Cram It, Doc!

Cram It, Doc!
Shawn went on to say that Dr. Major “doesn’t know crap about how she is now," adding, "I know my sister and I can say with certainty that Andrew has helped turn her attitude around. She is a much more pleasant person to be around now.” He added that he believes Amber "is doing better now than she has in 15 years.” For the sake of her growing family, lets hope he's right.

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Amber Portwood Biography

Amber and Leah (Teen Mom)
Amber Portwood is a star on MTV's Teen Mom. She is the mother of Leah Leann Shirley, whose father is Gary Shirley, Amber's on-off fiance... More »
Anderson, Indiana
Full Name
Amber Portwood