Lindsie Chrisley Says Boyfriend Will Ask For Dad Todd’s Permission to Propose Despite Prison Sentence

The reality star reflected on her burgeoning romance amid her father's prison sentence during a new episode of her podcast.

Lindsie Chrisley and her new boyfriend, Trent, aren't getting engaged just yet -- but if and when it does happen, Lindsie says she feels her beau will "fall more on the traditional side" when it comes to popping the question.

Specifically, she feels that Trent -- with whom she went Instagram official just last month -- would ask her dad, Todd Chrisley, for his permission to propose. Which might be a bit "tricky" since her dad is serving a 12-year sentence in federal prison for tax fraud.

Lindsie opened up about her romance during a recent episode of her podcast, Southern Tea, where she reflected on how difficult it would be for Trent to even get to know her parents, nonetheless asking for their approval of his proposal.

"It's a tricky situation with my parents being incarcerated. What would that even look like? How do you even approach that?" Lindsie shared.

Todd and her stepmom, Julie Chrisley, were convicted on fraud charges in November 2022 and reported to prison in January.

Todd is serving his 12-year prison sentence in Pensacola, Florida, while Julie is serving a seven-year sentence in Lexington, Kentucky. They are both appealing the conviction and have spoken out about how they are optimistic their convictions will get overturned.

"How many visits would be appropriate to do that?" Lindsie pondered with regards to asking Todd for his permission. "You don't just sign up and go to a weekend visit and be like, 'Hey, by the way, nice to meet you. I want to marry your daughter.' Like to me, that's not appropriate."

Lindsie was previously married to Will Campbell for nine years before they announced their decision to divorce in July 2021. Their divorce was finalized in October of the same year. The pair share a 10-year-old son, Jackson.

Because of her experience with divorce and her young son, Lindsie explained that the possibility of getting married again comes with more challenges and considerations.

"I think you also have to consider my situation, if I got remarried, and there are children that are involved," she said. "I don't have a second chance to mess up again."

Lindsie added, "If you go through two divorces, the problem is likely you... [and] two divorces are just not something that I really want on my rap sheet."

That being said, she isn't against the idea of getting married again -- she just would do things very differently than how she did things before. Namely, she wouldn't live with Trent before they tied the knot.

"I feel like I lived with Will before marriage when we were in college and we lived together pretty much all through college, post-college through engagement and then marriage so like nothing really changed [when we got married,]" Lindsie explained. "While I think there's some benefits of that, I also feel like everything was just the same."

"There was no separation between what marriage actually should be and what we were already doing. And I would just not do that again," she added. "I just think that it takes away a lot of the excitement and the newness and the settling in and the becoming one."

With regards to how Trent might go about getting to know Todd well enough to ask him for permission to propose, Lindsie didn't offer any concrete suggestions but made it clear it's a subject very much on her mind.

For more on Lindsie's relationship with Todd and Julie as they serve time behind bars, see the video below.