Kristin Cavallari Narrates Disappointing Reunion With Boyfriend 'I Lost My Virginity To': 'Put Me On Blast'

For Kristin Cavallari and her 8th-grade ex-boyfriend, there was no going back to how things were, at least not on her podcast!

The reality star got the shock of her life when her ex-boyfriend, whom she lost her virginity to years ago, was the opposite of her expectations.

Kristin Cavallari is currently basking in her single status after divorcing her estranged husband, Jay Cutler, in 2022, after nine years of marriage and three children.

In her March 25, recap episode, Cavallari spoke about a recent stop on her "Let's Be Honest" podcast tour where she had a surprise guest join her on stage, her middle school boyfriend, Johnny.

She shared that she lost her virginity to him in the 8th grade, and their unexpected reunion sparked thoughtful reflections on the other relationships she entered into after their time together.

Their time together significantly impacted her life, leaving her with fond memories and feelings of sweetness and love. She recalls reconnecting with Johnny, engaging in conversations for a few weeks before an important moment.

Understanding his usual discomfort with such situations, the former reality star asked him questions beforehand to make him feel more at ease and set him up for success. The mother-of-three stated:

"I felt like he was nervous, and so because he was nervous, how he decided to channel that was to essentially give me a hard time and put me on blast. And it really threw me. It was not what I expected. I was really let down."

Cavallari noted a stark contrast between the person she had interacted with in the weeks prior and the performer on stage. Following the performance, Johnny's warmth and affection returned as he greeted her with a kind kiss and expressed a desire to spend time together. 

Per PEOPLE, Cavallari acknowledged that while her feelings about the situation were intensified by exhaustion and the demands of the day, it ultimately served as a profound reminder of her personal growth, especially about men in her life.

The business mogul hinted that viewers would get to see the full segment of the tour where Johnny appeared in her upcoming reality series "Honestly Cavallari: The Headline Tour,"which is set to air on E! this summer.

She revealed to her friends that the experience left her feeling "bummed" and caused her to reflect deeply on her relationships. Cavallari expressed her frustration with how she has often been treated, saying, "I've never understood why the men in my life publicly have always wanted to put me down."

However, she emphasized her self-worth, declaring, "I'm enough. I love myself," and vowed to focus on giving love to herself rather than seeking validation from others.

Having experienced personal ups and downs in her past relationships, particularly with ex-husband Cutler, with whom she shares three children, Cavallari is determined to start fresh in her dating life. 

Following her split from Cutler in 2022 and a brief relationship with influencer Mark Estes, she has been exploring dating apps since their breakup in September 2024.

However, she is reconsidering this approach, questioning whether engaging in these conversations was truly beneficial or just for momentary gratification.

Now, she plans to redirect her energy into self-care and is open to the possibility of a meaningful relationship when the right person comes along, without feeling the pressure to rush into anything.

During her appearance on the "Dumb Blonde" podcast with Bunnie Xo last year, The Blast reported that Cavallari shared candid insights about her brief romance with country star Morgan Wallen.

She openly referred to him as a "great f-ck buddy," expressing her desire for a casual connection in Nashville. The host agreed, noting that Wallen seemed eager to take on that role.

Their conversation sparked laughter as Cavallari confirmed the playful assessment. The two were first linked in September 2023, although Cavallari initially dodged questions about their relationship in an interview with Andy Cohen.

She later confirmed the fling in November through a candid video on Instagram. During the playful conversation, Bunnie inquired whether Wallen was romantic when they were together.  Bunnie remarked, "I've heard he's great in bed," to which Cavallari humorously confirmed, "He was good in bed!"

Bunnie celebrated the endorsement with an enthusiastic shout, "We got another one to confirm! Morgan, slay, brother, slay!"

Cavallari showered the singer with praises, describing him as a "good guy" with a big heart and reflecting positively on their first date when he was a true gentleman. She mentioned that her children were thrilled to meet the country star. 

Although she has "nothing but good things" to say about him, the businesswoman revealed they have not spoken in nearly a year.

She expressed that one aspect of their relationship left her feeling unsettled. The former reality star was shocked that Wallen was not "completely enamored" with her, which was a new experience for her. 

This feeling of not having the upper hand in her short-lived romance with the "I Had Some Help" singer was something she found challenging and difficult to understand.

From the outside, her divorce may look like an easy decision, but The Blast shared last year that the fashion designer confessed that she never wanted a divorce. Cavallari was married to Cutler from 2013 to 2022, and she never dreamed of them not spending holidays as a married couple with their kids.

She expressed disappointment about not having a complete family unit during Christmas despite her desire to move on from Cutler. The TV personality also reflected on her experiences growing up with divorced parents, stating that she never wanted to face a similar situation herself. 

Although she acknowledges that feelings of loss sometimes resurface, she remains focused on the reality that they are no longer a family together.

The Uncommon James founder still does not "regret" anything about their "toxic" romance because "so much good" came out of it. However, she admitted to "repeating a pattern" with her dad when she started dating the former NFL star.

Kristin Cavallari's new project will indeed serve sizzling hot tea!