Teen Mom: Leah Messer & Jaylan Mobley Relationship Timeline

Leah Messer

Jaylan Mobley "Teen Mom 2" fans are convinced Leah Messer and her boyfriend, Jaylan Mobley, are expecting their first child together.

Leah Messer is engaged! The “Teen Mom 2 ” star announced her engagement to boyfriend Jaylan Mobley in an August 21 Instagram post. Leah shared photos of the beach proposal alongside the caption, “Two souls, one heart ❤️ It’s official!! 💍.”

In honor of the couple’s recent engagement, here’s a look back at Leah and Jaylan’s relationship.

Leah Messer and Jaylan Mobley’s Relationship Timeline

September 2020

According to Entertainment Tonight, Leah met Jaylan at an ESPN and Army event in September 2020. Leah told ET in September 2021 that she followed Jaylan on Instagram after the event to build her network.

February 2021



The relationship was a slow burn. The two went on their first date five months after meeting.

Leah told Entertainment Tonight that their romantic relationship started with an Instagram DM.

“In February of [2021], we connected through DMs and he asked me on a date,” she told the outlet in September 2021.

She also revealed a few details about their first 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,” she told the publication.

August 2021

Leah told ET that she and Jaylan took their relationship to the next level while on vacation in Costa Rica that same year.

“We officially became exclusive during our trip to Costa Rica, when Jaylan asked me to be his girlfriend over a sunset dinner! It was perfect,” she told the outlet. “This makes nearly a month, but we are excited to see what the future holds.”

September 2021

In September 2021, Leah and Jaylan became Instagram official. On September 10, Leah shared her first photo with Jaylan. In the photo, the two are sitting on a bench. Jaylan is kissing Leah on the cheek.

Two days later, Leah shared more photos of Jaylan on Instagram. This time, the “Teen Mom” star  shared a collection of photos documenting their relationship. The post included photos from their Costa Rica getaway and photos of Jaylan hanging out with Leah’s daughters.

April 2022

In April 2022, Leah and Jaylan took their relationship to the next level. On April 1, Jaylan took to Instagram to announce that he and Leah had bought a home together.

“Proud to be a First Time Home Owner! 🙌🏾 I am so thankful and blessed and still speechless to own this home 🙏🏾,” he wrote in the caption of the post.

“Surprise! [Leah Messer] ❤️ I’m proud of you for selling your first home and so I wanted to surprise you with a new home, our home,” he continued. “We deserve this! You deserve this! 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!”

Buying a house isn’t the only commitment the two made in April 2022. Shortly after the house announcement, Jaylan revealed he and Leah had adopted a dog.

On April 8, Jaylan shared a picture of him and Leah with their new puppy on Instagram.

“Everyone meet my boy Blue 💙🤟🏾 Thank you baby for the surprise [Leah Messer] 😭💙,” he wote in the caption.

August 2022

Jaylan pops the question to Leah on the beach.

Stay tuned for more updates!

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