'I Was Not Staring!': The Funniest Dating Mishaps on 'Chrisley Knows Best' & 'Growing Up Chrisley'

“Chrisley Knows Best” is a show about a family that loves each other. Unfortunately, some of their attempts to find a new special someone to bring into the family have gone woefully awry over the years.  

Even Todd and Julie, who have been married to each other since 1996, sometimes struggle when it comes to keeping the romance alive with a night on the town. Whether it’s Todd putting his foot in his mouth, a prank from Savannah, or Chase just bungling things, the Chrisley family has had some pretty rough dating mishaps on the show. 

As fans of “Chrisley Knows Best” wait to see what new adventures (and misadventures) the family gets up to next, we thought it might be fun to take a look back at some of the funniest moments involving the Chrisleys' love lives on the show over the years. 
 

Chase Brings Home A 'Stripper'

In the Season 6 episode appropriately titled “A Date With Destiny,” Chase brings home a date that he’s sure will irk his family, which is his whole goal. 

After Todd, Julie, and Savannah attempt to surprise him with a blind double date (more on that later), he gets his revenge by hiring an actress friend of his to pose as a stripper and his new girlfriend. While the family sits around the kitchen sipping hot chocolate, Chase comes in with “Destiny,” who immediately isn’t fitting in. 

She starts by asking if they have any alcohol to go with her hot chocolate. She then expertly dodges the question of where and how they met, offering vague answers like “a club” and describing her profession as being “in the entertainment industry” as a dancer. 

“Do you do backup dancing for a performer or something?” Julie asks. 

“I mean, I guess you could say I back it up,” Destiny, whose real name is Erica, cleverly responds. 

Chase puts a cherry on top of the whole prank by telling his parents he and Destiny are talking about giving them grandkids. Todd sits there with his mouth agape, Julie can’t stop offering everyone more hot chocolate, and Nanny Faye… well, she actually seems into the idea. 

“Chase took me to a strip club and it was a lot of fun!” she says sweetly. 

After Chase and Destiny leave, the family starts to unpack what in the world they just saw. That’s when Chase returns to inform them it was all a prank to get them to stop trying to fix him up without permission. 

“She deserves an Academy Award," Todd concludes of Erica's performance. 

Faye And Chase Take Frances Speed Dating

In the Season 8 episode titled “Roller Skates and Senior Dates,” Nanny Faye and Chase make it their mission to get her sister, Frances, a boyfriend. 

Chase kicks things off by taking her to a speed dating event in town that’s specifically for senior citizens. He explains to Frances she'll have five minutes with each person before a bell rings and they rotate to another single. 

“Five minutes?!” Faye says. “Frances, I can’t even get my pants down in five minutes.” 

Moving right along, Chase sits at the bar with Faye and watches as Frances tries her hand at chatting up a variety of single senior men. While Chase is looking at whether or not his great aunt has chemistry with any of them, Faye keeps her eye on the real prize. 

“We’ve got to know about his pocketbook first,” she says. “First question I’m going to ask him is, ‘How much is in your bank account and do you have a yacht?’ If they don’t have the money to suit me then beat it.”

Unaware of her high standards, a man actually approaches Faye and asks if she’ll be participating in the next round of speed dating. 

“I’m just here for support, I’m a bit too young for this,” she says. 

Still, he persists and continues to flatter her. Eventually she asks the most important question: Does he have a yacht? 

“I can get one,” he says, which turns out to be the right answer for Faye, who eventually accepts a date with him.

Todd Puts Savannah's Date In The Hot Seat

In the Season 2 episode “Rules For Dating My Teenage Daughter,” Todd shows how protective of Savannah he can be when a boy comes to take her out on a date. 

Savannah had hit it off with former “American Idol” contestant Spencer Lloyd. However, Todd initially tells his daughter she can’t go out with him because he’s 19 and she was 17 at the time, which he finds “inappropritate.” Eventually, he relents on the condition that Faye accompany them because nothing says romance like a chaperone in her 70s. Even with Faye in place, when Spencer comes to the house to pick Savannah up, Todd won’t let him leave without sitting him down and laying out some rules for the night. 

“Spencer, don’t plan on doing anything with my daughter that you wouldn’t do with me,” Todd says. “Nanny is going to be riding shotgun to keep me from having to use a shotgun.” 

He adds: “I better not catch you doing nothing or I’ll cut it off and put it in his pocket.” 

Fortunately, the date goes well, mostly because Spencer and Savannah are able to bond over Nanny’s poor chaperoning skills as she sits at the bar drinking and chatting up a date of her own. 

Savannah Walks In On Her Parents

Todd tries to prove he’s still got some romantic moves left in him in the Season 9 episode “Blind-Sight." He organizes a night of intimate massages for Julie and himself while the kids are away. At least, that’s what he thought.

First he explains he’ll give her a rub down and then she’ll reciprocate. He even pitches some roleplay.

“I’ll be the naughty masseuse, and then you’ll be the naughty masseuse,” he says. 

Julie is excited and jokes she has a lot of knots in her back from “living with Todd Chrisely for 100 years.” 

Just as they’re getting into the romance of the situation and relieving some tension, more tension walks into the room. Savannah and her then-boyfriend Nic Kerdiles surprise them and end up seeing Julie basically naked and Todd only in a robe. Their plan was to invite them to dinner, but after seeing what was happening, Savannah’s goal simply becomes to get the heck out of that house as quickly as possible. 

Nic, meanwhile, is happy to see Todd doing his thing and even giggles a bit at the awkward situation. 

Chase Gets Catfished By His Sister And Dad

In this scene, Todd and Savannah played a clever prank on Chase to help him mark Valentine’s Day and teach him a thing or two about respecting women. 

The episode titled “My Chrisely Valentine” opens with Chase revealing he’s “juggling” a few dates this year. Todd doesn’t like it, though. He notes that if a guy had done that to Savannah, he’d “go off.” So, he makes it his mission to sabotage Chase.

He enlists Savannah’s help and the two of them create a fake Twitter profile to message Chase and trick him into falling for the new lady. He spends days texting what he thinks is a beautiful young woman who is interested in him and has no clue that, in reality, it’s Todd catfishing his son. 

Chase basically blows off his two original Valentine’s Day dates and decides to meet up with the fake girl. When he arrives at the restaurant with flowers and a giant teddy bear in hand, he’s shocked to see that it’s just Savannah in a wig. Just when he thinks it can’t get worse, Todd arrives from behind wearing a waiter’s uniform. 

“We are now considered your moral compass squad,” Todd says.

Although he’s upset, Chase clearly learned his lesson. 

Todd Says The Wrong Thing... A Lot

In the Season 6 episode “Emotionally In-Vested,” Todd sees Julie purging her closet of clothes she no longer feels comfortable in. Todd doesn’t like that she’s not feeling like herself enough to enjoy some of her nicer outfits, so he offers to take her out to a nice dinner. 

He should have realized something was amiss when he asks about her first outfit and Julie gets upset and has to go change it. Once they are out at dinner, his faux pas continue. 

When Julie notices a woman walk by in a red dress, she compliments it. Todd takes a look but lingers on the stranger a bit too long for Julie's liking, prompting her to ask why he’s oggling another woman on their romantic date. 

“That is a pretty dress, you’d look good in that dress,” he says. 

“Yeah, as you’re staring at her walking past you.” 

“I was not staring, you said 'Look at her dress,' I looked at the dress!”  Todd adds.

Todd says he thought Julie was “fishing for a compliment” and wanted to give it to her. However, she argues that his attempts actually made her feel worse as she’s a little self-conscious about her body thanks to her medication. Therefore, she doesn’t “feel comfortable in a dress like that right now.” 

Todd makes one more giant mistake when he tries to make her feel better by saying he likes a little “junk in the trunk.”

“If that’s intended to make me feel better, it doesn’t,” Julie says. 

Chase Can't Date In L.A.

In the “Growing Up Chrisley” episode "Welcome To La La Land," Chase decides to dip his toe into the dating scene in Los Angeles while he’s there with his sister. Unfortunately, he finds the women in L.A. are not exactly the sort he’s used to chatting up back home in Nashville. 

He goes out on a blind online “day date” with a woman who orders a smoothie and tries to convince Chase to go completely vegan. He tries to compliment her necklace and she uses it to explain chakras to him as well as the energy of the space. 

It doesn’t take long before they both realize they have “absolutely nothing in common.” Despite that, she continues to try to get Chase to try meditation in order to make his “aura more positive.” 

“If all the women in L.A. are like this, man, I just need to get on a plane right now and take my a** back to the south,” he says. 

The Family Gets Too Involved In Chase's Love Life

After Chase goes through a breakup, Todd and Julie seize the opportunity to try to fix him up with someone they approve of this time — despite Chase making it clear he doesn’t want his family’s help finding a date. 

The self proclaimed “Pimp Todd” enlists the help of their friends, whips out a whiteboard, and manages to land on a young lady named Victoria to surprise Chase with on a blind date. Meanwhile, Savannah decides to bring a second “option” named Sunny for Chase to the lunch.

Once he shows up to the lunch, it quickly becomes clear that his parents and sister are not only trying to fix him up, but they’re competing over which one he’ll go with. When Sunny offhandedly mentions grandchildren, he’s had more than enough. Embarrassed, Chase get up and excuses himself from the table and scolds his family for their scheme.