Third time’s the charm! Teen Mom 2 star Leah Messer has been engaged three times now, and she has received several stunning engagement rings 

The MTV personality first experienced love when she got engaged to ex-husband Corey Simms. Their relationship played out during the first season of 16 and Pregnant. The former couple got married in October 2010 but later divorced in June 2011 following infidelity issues and other roadblocks in their romance. The two share twin daughters Aliannah “Ali” Hope and Aleeah Grace “Gracie” Simms

By August 2011, the Teen Mom 2 star began dating ex-husband Jeremy Calvert, whom she later wed in April 2012, nearly one year before they welcomed their daughter, Adalynn “Addie” Faith, in February 2013. 

The parents experienced multiple problems throughout their marriage as they argued about Jeremy working in another town, leaving Leah to care for her three kids alone. Eventually, Jeremy and Leah divorced in June 2015. 

Although she later moved on with ex-boyfriend Jason Jordan in May 2018, the two didn’t make it to an engagement. However, Leah finally found love when she started dating fiancé Jaylan Mobley in 2021, making their relationship Instagram official in September of that year. 

“Two souls, one heart,” Leah captioned an Instagram carousel post in August 2022, announcing that Jaylan had popped the big question. “It’s official!” 

In several of the photos, Leah flashed her stunning ring to the camera, which was a classy circular rock in the center surrounded by countless diamonds. 

The couple enjoyed a whirlwind romance prior to sharing the exciting news with fans. Just six months after they went public with their relationship, Jaylan bought his lady a new home for them and her children. 

“We deserve this! You deserve this!” Jaylan captioned an Instagram post in April 2022. “I can’t wait to build, grow, and create generational wealth, legacy, and opportunities for us and our families. This is to the next chapter and really leveling up!” 

Prior to accepting Jaylan’s proposal, Leah teased the possibility of having children with him in an exclusive interview with In Touch

“All I know is that we love each other and, at the end of the day, that’s the foundation I wanna set for our relationship, my kids, our future kids,” she said. “And that’s kinda where we’re at.”

Scroll down to see photos of Leah’s engagement rings! 





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