Carly Waddell and attorney Todd Allen Tressler called off their engagement after two years together.
“I’m always real with you guys, so I’m going to be real with you now. I’m not wearing a ring,” Waddell said in an October 2025 social media video. “I did break off my engagement about a month ago. [My kids and I] are living in a new city. It’s not a decision that I personally made overnight.”
Waddell started dating Tressler in 2023, marking her first relationship since her divorce from Evan Bass. Waddell met Bass on season 3 of Bachelor in Paradise, and they got married in 2017. Waddell and Bass, who share daughter Bella and son Charlie, split in 2020.
As Waddell and Bass got into a coparenting rhythm, the singer contemplated dating again.
“I have this fantasy that one day I’m just gonna be out walking around and I’m gonna meet this, like, wonderful man and he is just going to wow me,” Waddell exclusively told Us Weekly in May 2023. “I’m manifesting that for myself. … I’m good alone. I’m, like, actually doing pretty good. We have such a good thing going on now that someone stepping in and, like, changing the way that we do life makes me really a little bit nervous now.”
Two months later, Waddell met Tressler. Keep scrolling to revisit their full relationship timeline:
July 2023
Waddell stumbled across Tressler, an attorney, on TV when he was interviewed by a local news station. She thought he was handsome and carried himself well during his on-air discussion. After weeks of thinking about him, Waddell slid into his Instagram DMs. In response, Tressler “liked” a handful of her uploads.
“I, in turn, ‘liked’ something of his before saying, ‘So are just gonna keep liking each other’s stuff?’ He told me he was old school and would love to call me sometime,” Waddell revealed via Instagram the next year. “I asked him out in the most awkward voice text ever that I thought would never send and then it [accidentally] did. He laughed and accepted.”
Waddell accepted Tressler’s offer for a date, adding that the outing was “magic.”
Four months later, Waddell revealed on “The Ben and Ashley I Almost Famous” podcast that she had a new boyfriend.
“He’s older than me,” she teased, opting to keep most details about Tressler private. “He’s literally everything I’ve ever wanted in a human. It’s so great to have him around when craziness is happening in my life.”
October 2023
Waddell proposed to Tressler on Halloween, gifting him an engagement ring. However, she opted against sharing their proposal story publicly.
March 2024
Waddell and Tressler made their romance Instagram official.
“Here’s what I have been up to all year. Loving my loveable lawyer who also told me that I taught him what real love is, and he has done the same for me ❤️,” she wrote, uploading a montage of photos together. “I was gonna soft launch … but here we are. I always do things a little differently [than] I probably should 🤣.”
October 2024
Carly Waddell and Todd Allen Tressler with her two children. Courtesy of Carly Waddell/ Instagram
Tressler proposed to Waddell during a trip to Costa Rica with her children.
“Here’s to a new chapter with my dream man, and then dream ring he put on my left hand,” she wrote via Instagram, referring to her custom two-stone James Allen diamond ring.
June 2025
Tressler moved in with Waddell and her kids to a new abode in Lebanon, Tennessee. (Waddell and her family previously lived outside of Nashville.)
September 2025
Waddell announced on October 1 that she called off her engagement “a month ago.”
“I feel very at peace with this decision,” she said in her Instagram video. “My kids are loving life in the new place. Honestly, dating after divorce and dating with kids is super difficult. You have to make tough decisions for yourself and for your family. So, that’s where I’m at.”
Tressler did not immediately address their breakup, though he scrubbed any joint photos from his Instagram profile.
