How Many Times Has Each ‘Teen Mom’ Girl Been Engaged? A Complete List of ‘Teen Mom’ Engagements

That's the look of true love, right there...
That’s the look of true love, right there…

Wedding bells will soon be ringing for a bunch of the Teen Mom franchise stars! Currently, three of the eight main girls from the franchise are engaged, as are several of the ‘Teen Mom 2’ dads!

With all of these ‘Teen Mom’ engagements and weddings taking place in recent months, The Ashley began to wonder which girls have been engaged the most. Here’s a listing of each ‘Teen Mom’ girl, in order of how many times they’ve been engaged.


jenelle evansJenelle Evans:    At least four engagements

‘Teen Mom 2’ star Jenelle sits at the top of the most-proposed-to list, as she has accepted proposals from at least four different guys in her short 24 years of life. While it’s rumored that Jenelle may be engaged to her current soulmate, David Eason, the ‘Teen Mom 2’ star has yet to confirm the news. Jenelle’s previous soulmates—Andrew Lewis, Gary Head, Nathan Griffith and Courtland Rogers (whom she eventually married)—all asked Jenelle to be their wife but the relationships eventually went sour.

amber portwoodAmber Portwood:    3 engagements 

‘Teen Mom OG’ star Amber Portwood is currently engaged to Matt Baier, but before meeting him, she accepted a proposal from her baby daddy, Gary Shirley, on two different occasions. (Who could ever forget Gary’s classic proposal-via-Walmart-ring, or the proposal in which Amber screamed at him on the beach! #GoodTimes) The Ashley is counting Gary’s proposals as two separate ones since the couple did break up and start over in their relationship between proposals.

Leah MesserLeah Messer:    2 engagements

Leah Messer has been engaged twice—and both times ended in her actually walking down the aisle! Leah, who accepted proposals from Corey Simms and Jeremy Calvert, is currently the only ‘Teen Mom’ franchise cast member to get married twice. Unfortunately for Leah, both marriages ended in divorce.


Maci BookoutMaci Bookout:    2 engagements

‘Teen Mom OG’ star Maci Bookout is currently engaged to Taylor McKinney, the man she plans to marry in October, but before meeting him, Maci was engaged to her first baby-daddy, Ryan Edwards. The couple ended up calling off their wedding before they could ever walk down the aisle.


chelsea houskaChelsea Houska:    1 engagement

Chelsea Houska will marry Cole DeBoer—her first and only fiance—in October. The ‘Teen Mom 2’ star was in a long, on-and-off relationship with her baby daddy Adam Lind (and even accepted a promise ring from him), but was never officially engaged to Adam. Chelsea has stated that she’s happy she waited until she found the right man before getting engaged.


kail lowryKail Lowry: 1 engagement

‘Teen Mom 2’ star Kail Lowry has only been officially engaged once—to Javi Marroquin, whom she married in 2012. Kail was in serious relationships with Jo Rivera and Jordan Wenner, but was never engaged to either man.  Although Kail’s marriage to Javi has soured, he remains the only man who Kail has accepted a proposal from.


catelynn lowellCatelynn Lowell:    1 engagement

‘Teen Mom OG’ star Catelynn is currently married to her junior high school sweetheart, Tyler Baltierra, and, although Tyler proposed on two separate occasions, he remains the only fiance Catelynn has ever had. (The couple never broke up; they simply “renewed” their engagement with a new ring after cancelling their wedding.)


farrah abrahamFarrah Abraham: 0

Farrah is the only ‘Teen Mom’ girl who has never been engaged. She recently confirmed that she has purchased an engagement ring (for herself, naturally), but she has yet to have a man slip an engagement ring on her hand.

Like this post? Check out some of The Ashley’s other fun reality TV lists here!

(Photos: MTV, Instagram)


  1. Actually Leah’s marriage to Corey ended in divorce. As far as anybody knows she’s still married Jeremy Calvert and they have their daughter Adalynn.

  2. Farragut tries to make out that her and Derrick were engaged and he was “the love of her life” but it’s easy to rewrite history when the other person isn’t around to tell their side of the story. In her episode of 16 & Pregnant she treated him like dirt and wanted nothing to do with him but yet that never gets brought up when she’s crying those crocodile tears whenever his name gets brought up. She should let the poor guy rest in peace and stop using his name to gain sympathy because it’s all an act!!

  3. Bahahahaha purchasing your own engagement ring???……….shows you how messed up she is right there, that’s soo hilarious because its so pathetic. OMG…lol

  4. I didn’t remember that Jenelle was engaged to Andrew. I barely remember seeing him on 16&P/TM2 let alone them being engaged. Was that before she was on TV?

  5. So the only reason anyone wanted Jenelle was free money and fame. She’s not relationship material as each has not only gone sour they went violently bad according to her. Not to worry tho this one won’t because he’s probably actually beating her. And she won’t call Bill on the truth

  6. I thought Kailyn and Jo were engaged briefly? I remember from their 16 and pregnant reunion they announced that.

  7. Derrick never proposed to Farrah…in fact he took the hard way out. Farrah needs a major attitude adjustment, not to mention getting some parenting skills. Sophia is becoming a carbon copy of Farrah…a bitch!!!

  8. Cue you need to change your attitude: when you are the only spinster who was never proposed to in a group, while the half of the others are definitely not such a good catch either.

      1. It’s pretty easy to make claims about someone who’s dead. She’s claimed they were each other’s “soul mates, loves of a lifetime” too.

        And, we all saw how SHE treated him on her 16 & Pregnant.

        I claim she wouldn’t have custody of Sophia, if he were still alive.

  9. I laughed seeing this article. What stats need to be shown is how many different relationships these girls have been on that the soul mate has met their child/children counting all the ones we see on the show and the ones we know about from social media that just didn’t last long enough to be on the show. When you have that total, add up all of the men who had stable jobs at the time, and subtract the 2 #s. Now that would be a good read.

    1. Riddling? Do you mean RITALIN? Which is a stimulant? Yeah, I don’t think she needs ANY of that. Xanax, maybe…

  10. I love the Chinelle pic with the description next to it. These articles always make me laugh. Also, I can’t be the only one not surprised Ferret bought herself an engagement ring

  11. I think the reason Jenelle has been proposed to so many times is just because all her boyfriends are losers that see dollar signs if they get her to marry them. It can’t be her personality.

    1. Yes, if it wasn’t meant to be then so be it. But no, not all of them are good moms. I’m sure each of them have had their good mom moments but some of them don’t deserve to be in their children’s lives. No parent is perfect, we all make mistakes but to be a good parent it take sacrifice and hard work, both some of these girls have never done in their lives.

  12. Great article… However, Kail and Jo were engaged before. They announced it to Dr Drew on the season finale of 16 and pregnant if I recall 😉

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