The father-daughter duo made their annual appearance at the gala sporting event held at Churchill Downs in Louisville, Kentucky, on Saturday.
Larry took to Instagram to share some snapshots from their outing, and to show off their color-coordinated outfits.
"It’s that time of year again. The @kentuckyderby weekend is here!" the proud dad wrote. "Even though our favorite event The Barnstable-Brown Party won’t be back until next year, we decided to head out on this beautiful day to Churchill Downs racetrack in preparation for The Kentucky Derby."
"Dannielynn 'finished first' in her @jovanifashions pant suit and a beautiful white flowered fascinator. She said she wanted to wear something entirely different than she had in the past. I guess that means no more 'little girl' dresses??" he continued. "She cleaned out the chocolate brownies, ice cream and nachos while at the same time critiquing my outfit. 🤷♂️"
The trio of pics also showed off his daughter's bejeweled facemask, and featured a snapshot of the pair at the track together.
"She is clinging to the female teachers," he shared, adding that his daughter had been pushing him to date. "She's clingy to her girlfriends' moms and she’ll say things like, 'Do you want to adopt me? Would you be my honorary mother?' She tends to do that a lot."
At the time, he also shared that Dannielynn didn't ask too many questions about her mother, but had faced some awkward moments when she read stories about her family online. But despite the struggles of being a single dad, Larry expressed how proud of the young woman Dannielynn was turning in to.
"The other day, she had a friend whose fish died and she said, 'Don't worry about your fish, it's up there with my mom. My mom's taking care of your fish and it’s gonna be OK,'" he recalled. "It was something that she came up with. It was true from the heart and that's how she deals with it and I'm proud that she is who she is."
See more on the intimate interview in the video below.