Leah Messer’s Relationship History

Leah Messer

Getty Leah Messer

Teen Mom star Leah Messer has lived a large portion of her life in front of cameras. Viewers have watched her since she was featured in an episode of MTV’s “16 and Pregnant.”

The reality star is the mother of three daughters: twins Aliannah “Ali” Hope and Aleeah Grace Simms born in 2009 and Adalynn “Addie” Calvert born in 2013.

Since joining the cast of “Teen Mom 2” in 2011, and the repackaged series “Teen Mom: The Next Chapter,” Messer has been in several relationships captured by MTV.


Leah Messer Was Married Twice & Has 3 Children

Fans met Messer when she was expecting twins with her boyfriend Corey Simms. Still in high school and only dating for a month prior to learning of the pregnancy, Messer’s episode of “16 and Pregnant” showcased her struggles navigating motherhood.

After welcoming the twins, fans saw Messer and Simms’ relationship become strained. Messer had a brief interlude with ex-boyfriend Robbie Kidd before marrying Simms in 2010. The marriage ended in divorce shortly after in 2011.

In the same year, Messer began dating Jeremy Calvert. The couple married in 2012. Messer welcomed her third child in 2013. This marriage ultimately ended in divorce in 2015.

Messer began dating Jason Jordan in 2018, but the relationship ended shortly after in 2019. The mother of three shared about the relationship’s demise on the MTV show.

“My kids weren’t feeling it anymore either, not that they can determine who I’m going to be with, but they were picking up on the energy and it wasn’t okay,” Messer told producers.

“I really felt like I was in such a great place. I was ready to put my all in a relationship, it just wasn’t the right person,” she admitted.


Leah Messer Was Engaged to Jaylan Mobley

Messer’s relationship with Jaylan Mobley became official in 2021.

Entertainment Tonight reported the couple met through a project with ESPN and the Army in September 2020, and the couple connected on social media. The two took a trip to Costa Rica, where Mobley asked Messer to be his girlfriend over a sunset dinner. “It was perfect!” Messer shared, “we are excited to see what the future holds.”

In August 2022, the couple traveled to Costa Rica for their anniversary, where Mobley proposed to Messer.

A few days later, Messer revealed Mobley also gifted her three daughters their own rings to mark the occasion. Sharing the photos on Instagram, Messer wrote in the since-deleted post, “When I dreamed of this moment, this is exactly what I imagined it to be. A slow steady unconditional love, not just for me, but also for my three daughters that I cherish most in life. Thank you for everything you do for us. @jaylan_mobley We love you to the ends of the earth. It’s just US 4L.”

On October 11, 2022, the couple announced their break up. “While the last year has been tremendously exciting for both of us, we’ve realized that it’s best we walk separate paths,” the pair wrote on Instagram.

Messer and Mobley look to the future, finishing the statement, “We will forever have love and respect for each other, and we ask for privacy as we refocus and transition out of this chapter together.”

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