Carly Waddell<\/strong> <\/a>and attorney Todd Allen Tressler<\/strong> called off their engagement after two years together.<\/p>\n \u201cI\u2019m always real with you guys, so I\u2019m going to be real with you now. I\u2019m not wearing a ring,\u201d Waddell said in an\u00a0October 2025 social media video<\/a>. \u201cI did break off my engagement about a month ago. [My kids and I] are living in a new city. It\u2019s not a decision that I personally made overnight.\u201d<\/p>\n Waddell started dating Tressler in 2023, marking her first relationship since her divorce from Evan Bass<\/strong>. Waddell met Bass on season 3 of Bachelor in Paradise, <\/i>and they got married in 2017. Waddell and Bass, who share daughter Bella and son Charlie, split in 2020.<\/p>\n As Waddell and Bass got into a coparenting rhythm, the singer contemplated dating again.<\/p>\n \u201cI have this fantasy that one day I\u2019m just gonna be out walking around and I\u2019m gonna meet this, like, wonderful man and he is just going to wow me,\u201d Waddell exclusively told Us Weekly <\/i><\/a>in May 2023. \u201cI\u2019m manifesting that for myself. \u2026 I\u2019m good alone. I\u2019m, 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.\u201d<\/p>\n Two months later, Waddell met Tressler. Keep scrolling to revisit their full relationship timeline:<\/p>\n 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 \u201cliked\u201d a handful of her uploads.<\/p>\n \u201cI, in turn, \u2018liked\u2019 something of his before saying, \u2018So are just gonna keep liking each other\u2019s stuff?\u2019 He told me he was old school and would love to call me sometime,\u201d Waddell revealed via Instagram the next year. \u201cI 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.\u201d<\/p>\n Waddell accepted Tressler\u2019s offer for a date, adding that the outing was \u201cmagic.\u201d<\/p>\n Four months later, Waddell revealed on \u201cThe Ben and Ashley I Almost Famous\u201d podcast that she had a new boyfriend.<\/p>\n \u201cHe\u2019s older than me<\/a>,\u201d she teased, opting to keep most details about Tressler private. \u201cHe\u2019s literally everything I\u2019ve ever wanted in a human. It\u2019s so great to have him around when craziness is happening in my life.\u201d<\/p>\n Waddell proposed to Tressler on Halloween, gifting him an engagement ring. However, she opted against sharing their proposal story publicly.<\/p>\n Waddell and Tressler made their romance Instagram official<\/a>.<\/p>\n \u201cHere\u2019s 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 \u2764\ufe0f<\/span>,\u201d she wrote, uploading a montage of photos together. \u201cI was gonna soft launch \u2026 but here we are. I always do things a little differently [than] I probably should \ud83e\udd23<\/span>.\u201d<\/p>\n Tressler proposed to Waddell<\/a> during a trip to Costa Rica with her children.<\/p>\n \u201cHere\u2019s to a new chapter with my dream man, and then dream ring he put on my left hand,\u201d she wrote via Instagram, referring to her custom two-stone James Allen diamond ring.<\/p>\n Tressler moved in with Waddell and her kids to a new abode<\/a> in Lebanon, Tennessee. (Waddell and her family previously lived outside of Nashville.)<\/p>\nJuly 2023<\/b><\/h2>\n
October 2023<\/b><\/h2>\n
March 2024<\/b><\/h2>\n
October 2024<\/b><\/h2>\n
![\"Carly-Waddell-and-Todd-Tressler-October-2024-462191372_18463655104040843_654091298080689114_n\"](\"https:\/\/www.usmagazine.com\/wp-content\/uploads\/2025\/10\/Carly-Waddell-and-Todd-Tressler-October-2024-462191372_18463655104040843_654091298080689114_n.jpg?w=1000&quality=40&strip=all\")
<\/div>
\n Carly Waddell and Todd Allen Tressler with her two children.<\/span> Courtesy of Carly Waddell\/ Instagram<\/span><\/figcaption><\/figure>\nJune 2025<\/b><\/h2>\n