Teen Mom 2's Leah Messer’s Dating History: Corey, Jaylan, More

Teen Mom 2 fans have seen Leah Messer fall in and out of love over the years. While the TV personality has been married twice, fans have been able to see the beginnings and ends of many of Leah’s romances.

Leah was first introduced to MTV viewers when she was cast on 16 & Pregnant. The then-17-year-old was expecting twin daughters with her boyfriend at the time, Corey Simms. The pair had dated for just one month before Leah learned she was pregnant.

Leah gave birth to their twin daughters Aliannah “Ali” Hope and Aleeah Grace Simms in December 2009. After welcoming their daughters, Leah and Corey hit many roadblocks in their relationship as they navigated parenthood.

Their relationship suffered when Leah had an affair with her former boyfriend Rob Kidd, which led to her temporary separation from Corey. However, the parents eventually reconciled and got married on October 17, 2010.

Leah and Corey continued to deal with infidelity in their marriage and eventually divorced in June 2011.

While things didn’t work out between Leah and Corey, the Teen Mom 2 star continued to put herself out there in hopes of finding love.

The young mother began dating Jeremy Calvert in August 2011. After Jeremy proposed, the couple announced they were expecting a child in December 2011. However, Leah tragically miscarried the following month.

Leah and Jeremy tied the knot in April 2012, while the MTV star gave birth to their daughter, Adalynn (Addie) Faith, in February 2013.

After welcoming Addie, the problems in Leah and Jeremy’s relationship began to escalate. They started to argue about him working out of town, leaving her to look after the three children alone.

The pair eventually divorced in 2015 when they struggled to fix the problems in their marriage.

Leah later confirmed her relationship with Jason Jordan in May 2018.

“I think he’s definitely more mature than other guys that I’ve dated that are my age,” Leah previously told Us Weekly of Jason, who is 13 years her senior.

The couple became Instagram official in August 2018, though Leah was open about wanting to take the relationship slow. “The goal is just to learn [about] each other,” she told the outlet. “Even today, 7 to 8 months in, I’m not rushing anything. I just want to enjoy the time now.”

The relationship didn’t last and the mother of three confirmed they split in March 2019.

Leah found love once again and went Instagram official with Jaylan Mobley in September 2021.

“We met through a project Jaylan did with ESPN and the Army that was filmed and captured by one of my PAs in September 2020,” Leah told Entertainment Tonight in an interview published on September 12 about how she met Jaylan. “In growing my network, I followed Jaylan, and in February of this year, we connected through DMs and he asked me on a date. On our first date, he picked me up, took me to a lovely dinner at Bricks & Barrels in Charleston, West Virginia, and then we went to the Wiz Khalifa concert at the WV Power Park. It was amazing.”

During the couple’s anniversary trip to Costa Rica in August 2022, Jaylan got down on one knee and proposed to the reality star.

“It feels amazing,” the MTV personality told People on August 20 about their engagement. “I never imagined myself being here today, but I couldn’t imagine myself being anywhere else.”

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Unfortunately, Jaylan and Leah’s relationship didn’t last. Just two months after their engagement, the couple announced their split.

“While the last year has been tremendously exciting for both of us, we’ve realized that it’s best we walk separate paths. We are so grateful for the lessons, growth, and memories we’ve had in this relationship,” the pair said in a joint statement to In Touch on October 11, 2022. “So many of you have watched our love story unfold, and we hope that you’ll continue to watch our stories while we move forward as friends.”

Keep scrolling below to see Leah Messer’s full dating history.

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