Since she divorced from Jeremy, fans have gone crazy over Leah's love life. For months, she has denied rumors that she is seeing a new man. Now, the truth is finally coming out!
All of the Teen Moms have had high-profile relationships since the show began. Their new flings, pregnancies, and break-ups catch fans’ attention quickly. So how did Leah Messer keep her new boyfriend a secret for so long?
Leah has been unlucky in love since fans first met her on 16 and Pregnant . However, fans struggle to sympathize with the mother of 3, as her cheating has been the cause of many relationship woes.
Leah’s first marriage was to her high school sweetheart and first husband, Corey Simms. Corey is the father of twins Aleeah Grace and Aliannah Hope. Leah’s infidelity was a major issue in their marriage. They divorced in the summer of 2011, but she didn’t let that hold her back from another commitment.
She soon began dating Jeremy Calvert, who would go on to father her third daughter, Addie. She married Jeremy in April of 2012. Corey re-married in June 2013. His new wife, Miranda Patterson, has famously butted heads with Leah.
Leah’s marriage to Jeremy quickly began to fall apart. He moved out in 2014, shortly before Leah went to rehab to treat her addition to prescription pain pills. The couple divorced in June of 2015. After the divorce, Leah had several rumored hookups, including a long-term, on-and-off relationship with T.R. Dues.
Since the divorce, Leah and Jeremy have kept fans guessing about their relationship status. In one MTV clip, Leah sits down with her sister Victoria to discuss the Jeremy situation as her daughters play. “Jeremy texted me and said he wants to talk to me,” Leah confesses. “And he’s been commenting on every single one of my pictures and being super weird.”
“I think in a way, you kind of have a feeling of what it’s going to be about… Maybe he wants to go to dinner!” Victoria says.
But Leah isn’t having it. “Maybe it’s about Addie’s birthday party…” she says. “He asked me to do Addie’s birthday party together. Maybe that’s what it’s about.”
“I dunno,” Victoria replies. “He might be trying to get his way back in!”
At the time, Leah apparently had no interest in that! “Trying to get back together with me?” she says. “I sure as hell hope not!”
In another recent episode of Teen Mom 2, Jeremy and Leah had a serious discussion about their future together as a couple and Jeremy seemed hesitant to try again. “I don’t want to jeopardize what we have together to work out for 6 months or even a year and then everything falls apart,” he told her, adding that he didn’t want their daughter Addie to “feel that tension.”
Despite their insistence that things are done, Leah and Jeremy keep sparking rumors with their couple-y behavior. When Dr. Drew noticed the parents’ flirty quips during the reunion, he flat out asked the formerly married couple, “Are you guys rekindling your relationship?”
It was immediately apparent how embarrassed they were and they avoided answering the question. “This is just how we are,” Leah said. “We don’t flirt. We just… talk.”
Jeremy added, “Me and Leah have a very healthy relationship.” But that wasn’t enough for Dr. Drew.
He revisited the topic, demanding, “I’ve asked you now multiple times: Do you harbor any feelings for each other? Is this relationship being rekindled?” The couple’s silence said it all.
“I feel like we just get along!” Leah finally said defensively.
Jeremy groaned, “This is f–king awkward.”
Jeremy and Leah never confirmed that they’re dating again, but they also refused to say that they weren’t.
“I think the silence says whatever it says, and people can draw their own conclusions,” pointed out Dr. Drew. “But if you want to leave the silence to stand, so be it.”
Jeremy immediately replied: “So be it!” For months, their refusal to respond was the closest thing to an answer from Leah and Jeremy. Fans frantically tried to figure out the status of the co-parents based on all the conflicting signs.
Leah finally gave an inside scoop on the couple’s complicated situation to Kailyn Lowry on her podcast.
On getting back together, Leah stated bluntly on Coffee Convos, “No…I think he knows that. I mean, we’re friends and we get along great for Addie.” She eventually added, “I guess at first maybe I considered [getting back with Jeremy]… why not try it again for Addie’s sake’ but at the end of the day we weren’t happy. We didn’t do well together but we do great as friends.”
Though fans hoped that the pair would make things work, their efforts were ultimately unsuccessful. In February, Leah told Kailyn, “I am single AF…I just now started getting back out into the dating world.”
However, the star was clear that she is looking for something serious. “Someone told me that [using Tinder] is like putting ‘DTF’ on your forehead and I’m not that type of person, so I got the hell off of Tinder, and I’m never getting on any other type of dating app!”
Leah also complained about the challenges that she faces dating as a former “teen mom.” “It’s difficult [having three kids],” Leah confessed. “It’s really challenging trying to date.” But it looks like Leah has managed to overcome all obstacles and start up a new romance!
Meanwhile, Jeremy has had his own adventures in love. Earlier this spring, he announced his relationship with a new woman: Desi Kibler. “Road trips with babe…… #sohappy #grateful #shesamazing,” Jeremy captioned a picture of him and his new girlfriend.
Things seemed to move at a record pace, even for Jeremy. After only a few weeks, Desi tweeted, “Hate leaving Jeremy, makes me appreciate him even more every time I’m with him #timetostartplaninning” with emojis of a wedding ring, a house, and a family!
In fact, Jeremy was even willing to stay with Desi when she was busted for drinking and driving!
According to Radar Online, she was arrested for allegedly operating under the influence of alcohol on April 12 at 1:28 a.m. She was then charged with one count of OVI with blood alcohol concentration of .163, over twice the legal limit! She was also charged with possession of a controlled substance after police found an orange and white capsule pill on her. But the story did not end there.
Desi was arrested, booked, and released…. And then arrested again in the same night! At 3:17 a.m., she was allegedly stopped and charged with another DUI, as well as driving under DUI suspension! Apparently, this did not bother Jeremy, because he quickly came to her aid. He paid a $500 bond for the first DUI charge and $3,500 for the possession of drugs charge, Radar reported. Desi pled not guilty to both cases, which are still active. It was a bad sign for their fast romance.
Leah also seemed to be against her ex-husband's new fling. “I just don’t understand why someone chooses to settle and be unhappy,” Leah tweeted after Jeremy updated his relationship status. When fans called her out on the subtweet, she got more specific.
“Maybe ‘someone’ doesn’t want to be lonely, that’s why they settle for unhappiness,” a fan replied to Leah.
Someone else accused Leah of subtweeting Jeremy, writing, “And yesterday I saw a picture of @jcalvert505 with a girlfriend.”
“He can’t choose himself.. He’s gotta be in a relationship but that’s neither here nor there lol,” Leah tweeted. Clearly, she thinks that Jeremy should spend more time focusing on himself. But she insisted that the first tweet wasn’t about her baby daddy. “I’m not talking a bout him. I’m talking about anyone choosing to settle or not living life to their fullest potential.”
However, by June, there was trouble in paradise for the new lovebirds. Fans were quick to notice that Jeremy deleted all pictures of Desi from his Instagram… and then deleted his Instagram entirely!
“I have a type,” Desi tweeted at the time of the breakup. “Faithful and trustworthy.” She added, “If you’re going to act single, then be single.” Even though Desi may have been blindsided by Jeremy’s behavior, fans were not. Leah has been known to interfere in happy relationships in the past and this time may have been the same!
After all, Leah and Jeremy finally let it slip that they were hooking up during filming of the most recent season. A recent episode revealed that Leah accidentally let the secret slip to the crew in a conversation with her friend Kayla.
Leah shares the details of a phone call with Jeremy: his thoughtful apology and him thanking her for being a good mom to Addie. Kayla finally asks her, “So like…are you for sure done with the whole Jeremy situation?”
Leah clams up and stumbles when she tells her friend, “I mean, he has tried to…me to have sex with him a couple times. And it happened once and it happened a few months ago. We went to his house and I had to like hide walking out to the car the next morning so his mother didn’t see me”
Once her producer Brendan and the Teen Mom crew knew, all the pieces started falling together. As Leah and Jeremy sat on the couch together later that day, Jeremy quietly tells Leah, “Dude, I wanna say something so bad, but these people would go f**king ape s**t right now.”
“It’s nothing bad,” he continues, but Leah already knows what he is referencing.
“I mean, I told him that we hooked up,” she updates him.
Brendan then clarifies, “I suspected for a while, but I found out for sure today.”
Everyone turns to Leah, who defends herself, “It was an accident.”
Once fans knew about their secret hookup, things got even hazier! Jeremy has been in his feelings on Twitter lately, but for who? Since his breakup from Desi, he has tweeted, “When that one song comes on and your like “s**t” gotta be kidding me…… #memories #roadtrips #breakupsex” which seems to reference their initial trip together, but later tweets have sent mixed signals.
When he tweeted, “I reached out and it was pointless…” fans interpreted it as a commentary on why he and Leah have not gotten back together.
User @AshleyMaples27 replied, “Nothing is pointless . everything will work out for the best. You have to keep your trust in that but IMO Leah is crazy for not wanting you back.”
In another tweet, Jeremy shared, “How bad I wanna be a petty a**hole, but I’ll leave it alone f**k it… just saying this, nothing about the show had a thing to do with this…” Initially, it seemed as though the tweet was about Desi, as it was posted around the time of their breakup. But maybe he was heartbroken over Leah?!
If the show had nothing to do with their issues, maybe it was Leah’s new man! Though Leah insisted that she was single, it seems like fans were right to think she was falling in love just a few months ago.
“You make me wanna write a song,” Leah wrote on Twitter in February. Afterwards, fans immediately thought she was referring to a new love.
“Who is he who is he!?!” wrote Twitter user @jamieboston91.
User @HopkinsShilo tweeted, “Who is this mystery man? ??”
User @TraceyHtp chimed in, “Would love to see you with your happily ever after!”
However, Leah told Kailyn on her podcast in February that she did not think she would find her “forever” in West Virginia. She was insistent that she was raising her daughters as a single mom for now. Though there was frequent gossip about Leah’s hookups with Jeremy, there was no evidence of a new man in her life this spring…until now!
Rumors began flying after fans spotted flirty comments on an Instagram post of Leah’s daughters. Leah posted a photo of her daughters celebrating Independence Day by watching fireworks in Clearwater, Florida. User @raylansdad416 wrote, “the fireworks were incredible no doubt, but being with you was the most incredible part of my evening ;)” along with a kissing face emoji. Leah replied to the mystery man with a string of emojis, including smiley faces and a kissing face.
According to The Ashley’s Reality Roundup , Leah has found love again! Sources have revealed that she is dating a new man, 39-year-old Jason.
Evidently, they have been dating for several months, but Leah has kept the relationship quiet. The couple met through mutual friends. Jason has a two-year-old son with his ex-wife. They married in 2014 and divorced this past October. A former basketball player, he studied psychology and sociology at West Virginia Wesleyan University.
Jason currently works in medical sales. Jason has also dabbled in comedy. He has a series of YouTube videos chronicling the adventures of “West Virginia Meth Man.”
He films himself using a filter to distort his head and voice, while mocking meth use. The most recent video was posted two years ago. They are currently listed under “John Smith,” but it did not take Teen Mom fans long to uncover the true identity of “Meth Man.”
Reddit user RandR0088 questioned, “I Wonder if Leah has seen these lol.. grounds for break up IMO.”
CriminalVixen wrote, “She's really living her standard...”
-i-downvoted-you- added, “There’s plenty of fish in the sea but Leah goes down to the crick and reels herself in a catfish.”
Unfortunately, fans will not be seeing any more of her new beau anytime soon. A Teen Mom source has said that Leah “wants to keep this relationship more private,” so he will not be appearing on the show. Teen Mom 2 is currently filming Season 9.
In the meantime, Leah has been exploring other opportunities. She and fellow “Teen Mom” Kailyn have been brainstorming a new project. In addition to both going through pregnancies at a young age, they’re both divorcées, and they both have three children. There’s just one major difference between them: while Kailyn has three sons, Leah has three daughters! That gave the girls an idea.
“I’ve thinking [Leah Dawn and I] should swap kids for a few days to see what it’s like to be a mom of boys/girls,” Kailyn tweeted, adding, “#teenmom2.” She even addressed her tweet to MTV and the Teen Mom official Twitter, writing, “Let’s make this happen!”
Leah seems to think that taking care of Kailyn’s boys would be a break. She said on Coffee Convos, “I just think girls are harder in general. I see another mom with boys, and even as far as their hair, you’re like, I’m not waking up at 5 o’clock in the morning! … Comb it over! [No] braids or pigtails. And Gracie has to have four outfits out in the morning to choose from.” Leah added, “Girls are dramatic, too!”
Their co-stars seem on board with the spinoff idea. Chelsea Houska responded, “Yeess this would be cute!”
Maybe Leah would show off Jason on a new project of her own. We’ll have our fingers crossed!
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