Lindsie Chrisley on 'Tricky' Chance Her Boyfriend Might Want Dad Todd's Blessing to Propose amid Prison Stint

The 'Chrisley Knows Best' alum admitted that her boyfriend Trent would likely "fall more on the traditional side" when it comes to a possible proposal

Lindsie Chrisley is opening up about potentially getting engaged to her boyfriend Trent amid her parents Todd and Julie’s prison sentences, and why it would be “tricky.”

On the latest episode of her Southern Tea podcast, the 33-year-old Chrisley Knows Best alum reflected on how her boyfriend — who she went Instagram official with last month — would ask for her hand in marriage with Todd behind bars.

“It's a tricky situation with my parents being incarcerated,” she shared. “What would that even look like? How do you even approach that? How many visits would be appropriate to do that?”

Related: Lindsie Chrisley Debuts New Boyfriend Trent as Source Says She's 'Happier Than She's Ever Been'

She continued, “I mean, 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. So like, how would you handle that situation? I don't know.”

Lindsie added that she believes her beau would likely “fall more on the traditional side” when it comes to a proposal despite her parents’ prison stints.

In November 2022, Todd and his wife Julie, 50, were sentenced to a combined 19 years in prison for financial crimes. Todd began his 12-year sentence at Florida's Federal Prison Camp Pensacola in mid-January on the same day as Julie started her seven-year sentence at Federal Medical Center in Lexington, Kentucky. They're currently in the process of appealing their case.

Related: Lindsie Chrisley Confirms She Has a New Boyfriend — and Her Ex-Husband Will Is Also 'Seeing Someone'

On the podcast, the former reality star also opened up about what she would do differently when it comes to tying the knot again after her first marriage to ex-husband Will Campbell ended in divorce.

“I think you also have to consider my situation, if I got remarried and there are children that are involved,” she said of her son Jackson. “I don't have a second chance to mess up again and not to say that you know that I got a free pass the first time because I went through one divorce. If you go through two divorces, the problem is likely you.”

“But two divorces is just not something that I really want on my rap sheet,” she added. “And so that's why I would do some of these things just completely different and I feel like moving into a new place and a new marriage with kids and it being new for everyone and everyone having their own personal space within that space would be the way to do it.”

She added that she wouldn't live with someone before marriage as she did with her ex-husband.

Related: Savannah Chrisley's Parents' Prison Stints Makes Her Question Timeline for Marriage and Kids: 'Can't Move On'

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“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 and while I think there's some benefits of that, I also feel like everything was just the same,” she explained. “So there was no separation between what marriage actually should be and what we were already doing. And I would just not do that again."

“I just think that it takes away a lot of the excitement and the newness and the settling in and the becoming one [so] I just wouldn't do it again. I would focus my time on premarital counseling, because that's something that I did not do, which I should have done when I got married to Will and I would want it to be biblically based. That's very important to me.” 

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