It’s Official! ‘Teen Mom 2’ Star Leah Messer is Engaged to Jaylan Mobley: Get Proposal Details & See the Massive Engagement Ring

“I’m gettin’ hitched again, y’all!”

Leah Messer is hoping the third time’s the charm when it comes to marriages.

The Teen Mom 2 star is officially engaged to Jaylan Mobley, her boyfriend of less than a year. In photos [most likely sold to and] posted by People on Saturday, Jaylan can be seen getting down on one day while on the beach in Costa Rica on Friday night, proposing to Leah with a 4.7 carat(!) diamond ring.

Jaylan asked Leah to marry him “while taking a romantic stroll on the beach after the couple enjoyed a dinner prepared by a private chef,” People reports.

Leah and Jaylan began dating in September 2021, and bought a house together earlier this year. This will be the third marriage for Leah (who was married to Corey Simms from 2010-2011 and Jeremy Calvert from 2012-2015), and the first for Jaylan.

“I can’t even express how I’m feeling. I wanted this moment to be the perfect moment for her,” Jaylan told People.

“After all, a girl only gets one engagement in her lifetime. Oh…wait…”

Leah said she suspected Jaylan might propose, but was surprised at how he did it.

“[I] had no idea it was going to be like this,” she told the magazine.

Jaylan added that Leah’s three daughters— Ali and Aleeah (by Corey) and Addie (by Jeremy)— are not aware of the engagement yet.

“Um, guys? You know there’s this thing called the Internet that we can use to find stuff out, right?”

“The girls have been asking if I plan to propose, [and] I think the best way to tell the girls is for us to do it together. I have a surprise for them as well,” Jaylan said, adding, “I’m just looking forward to everything that we’re going to do together — making this commitment to each other, making a commitment to the girls, growing our family, and just doing this life together as one.”

In photos posted to their Instagram accounts on Saturday, Leah and Jaylan showed more of the proposal— and Leah’s massive diamond engagement ring. (Flip through the photos below to see the ring up close!)


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A post shared by Ḻєαн ᗰєѕѕєя ♕✰ (@leahmesser)

As for her third trip down the aisle, Leah says she’s planning to go solo this time around.

“Well, if you go on and change your mind and want me to scurry you down the aisle, let me know. I’ll need to get gussied up.”

“I want to walk myself down the aisle,” she said. “I say this over and over again. I’ve made it to where I am as a woman and a mom, and I want everyone to see that strength.” (For her first wedding, Leah walked down the aisle with her stepdad, Lee. For her second, she was accompanied by Lee and her long-lost dad, Gary, whom she would go on to use drugs with after reuniting.)

Leah’s also planning to shoot out a couple more kids in the future. (During past interviews, she stated that she was unsure if she wanted to have any more children.)

“But here I am, puttin’ on another weddin’ dress and firin’ up the ol’ baby cannon!”

“I’m looking forward to everything that the future has in store for us — our families coming together, the kids we’ll bring into this world together, growing businesses together,” she said. “It’s very open but I’m excited about it all.”

“Jaylan’s never been married,” Leah said during an interview back in April. “He wants that experience and I would never take that away from him. At the same time, for me, I don’t feel like marriage should change anything. I want to keep what we have now …  I don’t want it to change our love for each other, but I don’t think it’s going to either. I’m open to it.”

It appears that Jaylan got some help from several PR agencies (and the jeweler) to get that massive engagement ring for Leah. According to a post on the PR agent’s Instagram Stories, the group helped “secure” the ring for Jaylan, so it’s unknown if he paid for it, or if he paid full price for the huge custom ring.

As The Ashley previously reported, Leah and Jaylan are both set to star on Teen Mom: The Next Chapter, which premieres next month, so fans will get to see the events leading up to Jaylan popping the question.

RELATED STORY: MTV Sets Premiere Date for ‘Teen Mom: The Next Chapter’: Watch the First Trailer & See the Return of Jenelle Evans

(Photos: Twitter, MTV, Instagram)

52 Responses

  1. Yikes! These comments are super cringe. Can’t help but point out that a lot of what is being said is based on stereotypes and assumptions about Jaylen. Would y’all be saying the same if she decided to marry another Corey or Jerm? They’re “hard workers” while Jaylen is “a fame whore” with ulterior motives? Corey and Jerm are viewed as “victims” of Leah’s infidelities and substance dependency issues, while Jaylen is a “creepy guy” her children hate? Maybe, just maybe, Leah has grown up a bit and is now in her first real adult relationship? She’s nearly 30 years old and she’s done her fair share of dating since her last divorce. Maybe this is simply two adults who met and fell in love? Just sayin.

  2. Jaylan reminds me of Amber’s ex Matt

    Both TMOG fame whoors! What is Leah doing? Why would you blend families like this? This is not approved off and I’ll give it 1 year

  3. Girl….Just make sure you make him sign that pre-nup! He doesn’t seem like the type to NOT fight you for alimony/child support!

  4. Do you think she’ll cheat on this husband with Robbie too? Or was that just reserved for her first two husbands?

      1. These two feed off of each other. Both are all about themselves. How sad. Can’t wait for this show to go down.

    1. Yeah. He’s in the military. He works in the cybersecurity division of the Army.

      Its actually really accomplished.

      He has a Bachelor’s from West Point and a Master’s degree for WVU.

      it’s a better question what does a guy who went to West Point have in common with Leah Messer?

      1. I was curious and googled it. Jaylan has his credentials posted on LinkedIn – he actually didn’t get his bachelor’s from West Point. He went to the West Point prep school for high school and received his bachelor’s from Virginia Military Institute which is likely a fine institution, but not as selective as West Point.

        Nonetheless, what is a guy like him doing with Leah unless he wants access to the spotlight and she is his ticket.

        1. My Bad. He keeps mentioning he went to West Point, so I assumed it was for undergrad.

          Yeah VMI, is an okay school. I think West Point is harder to get into than some ivy league schools.

          I really just want to know what they talk about, or if he corrects her grammar all day long.

          1. Haha (re: the grammar comment). I guess Jaylan saying he went to West Point is like Farrah saying she went to Harvard. They did not receive degrees from the institutions, but they did technically attend. Seems a bit like credential inflation on Jaylan’s part since a bachelor’s degree from West Point can easily be perceived as prestigious as an Ivy.


  6. So…she’s jumping into another marriage AGAIN?! 2 seconds and they will be expecting a kid if she’s not already in early stages of a pregnancy. You had TWO failed marriages Leah, I thought you will be smarter than that and wait a lil’ longer.

    Who knows, maybe they won’t even make it down the aisle.

    1. September 2021 is less than a year ago, it’s only August. Plus in another article I saw, they’ve supposedly actually been engaged for awhile but just announced it now.

  7. So this happened Friday, as in, yesterday, and it’s already plastered all over the internet and they haven’t told her daughters yet? I’m sure they’ve found out by now. This guy is a fame whore for sure.

  8. He wants kids and she doesn’t want anymore…. I’m not sure why you would get married with that big of a blaring difference in what you want.

  9. all of the jeremy fans who wanted them to get back together aren’t gonna be happy about this, happy & excited for them though! ?

    1. Jeremy was a terrible husband and he’s a worse father.

      I’m glad Leah didn’t get back together with him. They were terrible together.

      1. Jeremy put up with her drug addicted a$$! He held the family together! But b/c he works 60hrs a week outside the state he’s the bad guy. Give me a break! Jeremy is a saver and is doing just fine, don’t worry about him.

        1. He still doesn’t see his daughter ever. Addie still cries all the time about not seeing her daddy.

          Look Leah was no saint in that marriage, she cheated on Jeremy with Robbie, and got addicted to opitates. And had a huge spending problem.

          But that doesn’t mean that he was a good husband.

          Also, facetime exists, no reason not to call your daughter a couple of times a week or even every night before bed and talk to her.

          Like he’s calling Corey out for not skipping three days of work to drive to Ohio for a routine doctor’s appointment, and always sends Papa Jeff (aka his dad). But how many doctor’s appointments has Jeremy been to? What’s even Addie’s Primary Doctor’s name? What’s her teacher’s name? All things I bet Corey could answer but Jeremy, nope.

          Yep, he’s provided and he comes from a long line of pipeline workers. Leah should have understood more what that would mean.

          But Jeremy to this day ain’t winning any father of the year awards.

          A lot of fathers work out of state, or are in the military and talk to their kids more often than Jeremy.

          FFS Javi was a terrible husband, but he was always there for his kid. He called Kail and Lincoln all the time to check-in. If someone deployed in the military can find the time, then someone working the pipeline can find the time.

  10. Good Lord, here she goes again. Anything to keep this show going. Same thing every time. Date, short time. Married for a short time, then divorce. You think she would figure it out. Wonder who she will blame when this goes bad.

  11. I get weirdo vibes from this guy. He’s so fake.

    Leah has said for years she didn’t want another marriage. Or more kids.
    This is all just odd to me. It wasn’t long before Jaylen that her and Jermy were still knocking boots.

    1. Agreed – something about him doesn’t pass the smell test. Very into social media, his public persona, and making a big display about everything. He doesn’t seem to pass Ali’s smell test either and she’ll have to live with him. I don’t want to root against her since somehow she is the most tolerable of all of the TM women, but this seems off – perhaps lyin’ hustlah vibes? Hopefully for the sake of Leah and the girlses, he’s just awkward and is indeed a real deal good guy. He’s educated so hopefully that will be a good influence for all members of the Messer-Sims-Calvert-Mobley household.

      Also those pants he wore for the engagement make me question his deal.

      1. Ali doesn’t like him? I haven’t watched the show for years, so I really don’t know. But when one of your kids doesn’t like someone, you need to listen to that. Leah clearly doesn’t care. The twins are definitely old enough now to know what’s what. I imagine Addie does too.

    2. I think its fair to say anyone who dates a TM star (mom or dad) qualifies as a fame whore.

      Kristina is an exception. But Javi, Chris Lopez, Jeremy, Nathan, Alnost Fanous, David, Cole, Mack .. All fame whores.

      Dude is creepy and I was under the inpression her girls weren’t crazy about him? The last thing they need is Daddy #3.

        1. Miranda is as much a fame whore as the rest–the only reason they stopped filming is because the fact that Corey cheated on her with Leah shortly after their marriage, was exposed. She did not want to continue with that story line so they stopped filming,

      1. And there are the hangers on of the hangers on trying to get their 15 minutes of fame. Years ago Jeremy had a girlfriend Brook Wehr – she and Jeremy started a clothing line (of course) called Calvert Wehr ?. And Javi’s baby mama Lauren was trying to make influencing happen while riding Javi’s / Kail’s coattails.

  12. Sure Leah, I’m sure you didn’t expect it. If the professional photographer, the private chef, the film crew, & the outfits didn’t give it away, the 4.5 carat diamond paid for with your own bank account should have. But we’re used to you lying, so no worries.
    Looks like you’re already starting the whole “growing your family” thing.

  13. Seriously, what’s so wrong with waiting until you really know someone before making these massive commitments???

  14. Guarantees one season’s worth of footage.

    The baby guarantees season 2.

    Season 3, the break up. Season 4, the divorce.

  15. I’m not surprised the engagement is happening. I just hope it’s the real deal and Leah isn’t just being love bombed by a guy who wants attention. But if they’re happy, congratulations to them.

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