The Most Awkward Things We've Witnessed On Chrisley Knows Best

Chrisley Knows Best does a few things best, and creating awkward moments for our viewing pleasure is one of them. Yes, the show's cast is always dressed to the nines, their house is huge, and they always have fun trips planned ("I expect a certain standard," Todd Chrisley has even said), but that does not mean the family does not also have a knack for making us cringe as we watch from our couches. And yet, we all keep watching.

This famous family has been opening up their lives to television audiences ever since 2014. We've been there for their highs and lows and practically every uncomfortable moment in between. Though the Chrisley family has made themselves buckets of cash over the years, Todd has said they "still have the same issues that parents who are making $40,000 a year." However, their awkward encounters are only magnified — you know, because they all happen on national television. Here are the most awkward things we've witnessed on Chrisley Knows Best.

When the Chrisley family takes a trip to Las Vegas during Season 4, Nanny Faye Chrisley only wants to do two things: gamble, of course, and check out a famous show. As her ride-or-die grandson Chase Chrisley says, "If my grandma wants to see a show in Vegas, then I've got the perfect one for her to see." So the two of them go on their way to see it — and it ends up being a pretty awkward encounter for all of us.

Out of all the live performances they could have headed over to, Chase decides to take Nanny Faye to see Chippendales. Any other grandchild in the world might feel super uncomfortable taking his grandmother to a strip show, and as if watching the production from the crowd isn't enough, Nanny Faye is even brought onto the stage as a special guest!

However, walking away with a wet t-shirt as a souvenir, it seems Nanny Faye really enjoyed herself. As a thank you gift, she even uses her gambling money to get her grandson the presidential suite for the evening. "This was my reward for being such a good grandson," Chase later tells his dad.

Any time the Chrisley kids head out on a date, it's most likely going to make for an awkward viewing experience. (Hey, Chrisley Knows Best knows entertainment.) When 10-year-old Grayson Chrisley hangs out with a girl from school during Season 4, it quickly becomes a family affair. Literally.

Grayson's two sisters and Nanny Faye Chrisley accompany him as he meets up with a girl named Shelby to grab some gelato. When Nanny Faye sees Shelby, she says, "Oh, look how pretty!" And it's probably the nicest thing happens during Shelby's outing with Grayson. 

At one point, Grayson spills ice cream on himself. There's another moment where his sisters snap not-so-subtle selfies with him and Shelby in the background. During an uncomfortable silence between him and his date, he even turns around to Savannah Chrisley and asks, "What do I say?" Now, the ultimate question is, will there ever be a second date with Shelby? Maybe not; at least not with his family — and all of us at home — awkwardly watching.

If you date a Chrisley, you're dating the entire family. When Chase Chrisley tells his family he has a girlfriend in Season 6, his family tells him they want to meet her. So, he obliges, and Destiny swings by the house in a low-cut dress. When Julie Chrisley offers her some hot chocolate, Destiny asks for some alcohol to go along with it. The tension is as thick as whipped cream.

As the two snuggle up in the Chrisleys' kitchen, Chase explains how they met at a club. As the family questions his girlfriend some more, they find out she's a dancer. Julie asks if she did "backup dancing, like, for a performer," to which Destiny replies, "Um, I guess you can say I back it up." Nobody seems to know how to respond — not even Todd Chrisley, of all people.

To break the tension, Nanny Faye Chrisley eventually chimes in. "Chase took me to a strip club," she says. "And it was a lot of fun!" Later on in the episode, Chase reveals it was all a prank, but not before we were all feeling very uncomfortable.

While everyone in the Chrisley family has awkward dating stories, Savannah Chrisley seems to have it worst. "Savannah is my baby girl," Todd Chrisley says when she first brings Nic Kerdiles home. "It's my job as her dad to run these guys through the wringer." Meanwhile, Julie Chrisley decides to make Nic feel at home by cooking him French food, as a nod to his heritage. At first, he's flattered, but then Todd goes all Todd on him. "I figured since you're going all French on my daughter, we'd go all French on you," the patriarch says. Awkward.

Later on, Todd takes Nic out shopping at an expensive store. "I got a little test up my sleeve," he the patriarch admits. He wants to see if Nic will take advantage of the Chrisleys' wealth — and he doesn't.  

Todd decides to drill Nic even further and ask why he believes Savannah is "the one" — aside from the fact that she's related to Todd.  "I mean, I love her enough to get through that," is Nic's response. It's a bold thing to say to your girlfriend's dad, but it didn't totally backfire: Nic's relationship with Savannah lasted for several years.

Nanny Faye Chrisley always has something funny to say, and she sure doesn't disappoint when she goes on a nude retreat during Season 7.

Let's back up: Todd Chrisley's mom ends up at the nude retreat without known she's going to a nude retreat. Nanny Faye had recently met up with her childhood friend Susie, who asks her to join her on a getaway, "I really think you're going to like this place," she tells Nanny Faye. Susie explains that it's "a resort for seniors," and Nanny Faye is intrigued. Susie, however, forgot to add that "the clothing is optional."  

When Nanny Faye doesn't answer her phone for hours, Todd becomes worried. He tracks her location and drags Chase Chrisley along. They end up finding her out in the middle of the woods at the nude retreat — fully clothed. Of course, Todd navigates the camp like only Todd can.

When Savannah Chrisley was named Miss Tennessee Teen in 2016, Todd Chrisley missed it. It was the only pageant he did not attend, and he's always regretted not being there for her big moment. In fact, he regretted it so much that he decided to throw a party to recreate it during Season 4. What's supposed to be a small household party turns out to be a large family affair; Todd rents out a venue and even picks out a pageant appropriate gown for his daughter to wear. Obviously, Savannah is not having it.  

By the time the party rolls around, she decides to make the best of it — and throw her dad for a loop. When he pulls her on stage to ask her classic beauty pageant questions, she gives a shout out to every family member but Todd. "If he wants a show, I'll give him a show," she admits later in an interview. For example, when Todd asks her who her role model is, she answers with, "My mother is my role model." It's definitely not who he was hoping she would say. And then, Savannah pours salt on the wound: "Because she's shown me how to put up with a man."

There are many things Todd Chrisley can't stand. He hates people in his home, people touching his stuff, and Julie Chrisley's best friend Lea. Regardless, when Lea's water is turned off during Season 2, Julie insists that she come stay with them. She's pregnant and uncomfortable, so her hosts have her sleep in their bed... which leaves Todd stuck on the sofa. It only escalates from there.

Even though Todd isn't happy with where their houseguest is sleeping, he still goes upstairs to wish Lea goodnight. And he quickly comes to regret that decision. She suddenly grabs her stomach in pain. Todd doesn't want to touch her, so he rushes to try and find just the person for the job — Julie — but she can't be found. He tells Lea to lay down for a second. She replies, "I don't think I have a second, Todd."

His entire family knows what he's thinking. "If she has a baby in my dad's room, we will have to move," Chase Chrisley admits. Lucky for them, they didn't have to list their house. "I think it just might be gas," Lea says before getting back in bed.

Chase Chrisley loves to flirt — so much so that he finds himself with more than one Valentine's Day date during Season 3. When Todd Chrisley finds out about this situation, he's less than impressed. To teach his son to not lead on multiple ladies at once, Todd decides that he's going to catfish Chase. Savannah Chrisley helps her dad set up a profile to text her brother some flirty message as a character named "Lia," and it gets pretty cringeworthy pretty fast.

During his first date, Chase is so into this fake girl that he's texting her at the table. "How rude is he," Todd says, before adding, "Aww, he sent me the little heart emojis!" And then, Todd receives a more explicit message. So. Much. Awkward.

After lusting over "Lia" all day, Chase sets up a time to meet with her. When he gets there, it's Savannah in a wig. "So I've been texting daddy this whole time?" He asks her. "That's — ew." You said it, buddy.

Todd Chrisley's kids stress him out. That much is obvious if you've ever watched an episode of Chrisley Knows Best. Because of that, he's worried that he's headed for an early death. During Season 4, he starts thinking about his own funeral, which leads him to set up a rehearsal for it to make sure everything is Todd-approved. However, seeing as how he's still very much alive, Todd's "funeral" turns into an extremely peculiar experience for his family.  

When they all show up to the church, the most expensive casket is on display. The flowers are pure white, as Todd requested, but he notices that the casket piece is not right. "You should see what it looks like inside. It's scary!" his daughter Lindsie Chrisley says. When he opens it up, out pops Savannah Chrisley! That kind of scare really could have killed anybody. "Y'all are some sick, twisted people," Todd says. They all quickly make a point to remind him that it was his idea to have a rehearsal funeral.

Surprisingly, Todd Chrisley gives his "semi-approval" of Savannah Chrisley's boyfriend Blaire Hanks during Season 3. Since they were in a long distance relationship, Todd called the country singer up to have him surprise her at her graduation party. Yet, things turned awkward fast when Todd found out the night beforehand that Savannah was no longer speaking to her boyfriend. Todd decided to have him come anyway. Yikes.

"She can't get rid of me that easy," Blaire even told Todd before heading out on stage. Obviously, Savannah was shocked — and also very irritated. "Sometimes there are things that Todd Chrisley just can't fix," she said. However, her dad seemed to really make the whole situation better in the end.

When Blaire started singing, Savannah started crying. She realized he really did understand her as she listened to the lyrics he had written. As she got all mushy gushy and forgave him, Chase Chrisley cut in and suggested that "somebody needs to call Nicholas Sparks." Unfortunately for them, their relationship didn't last long in the end. We guess it wouldn't have been a very good Sparks novel after all.

The Chrisley household always seems to be crazy, and during Season 2, Todd and Julie Chrisley decide they need a break. They book a hotel room for the weekend and leave their kids to look after themselves. If you're a fan of the show, you know that's a frightful idea. Chase Chrisley has his own plans in mind, and his parents quickly find themselves in the middle of it. It's unusual considering they're usually the ones making their kids feel awkward, not the other way around.

"I'm going to get a hotel room," Chase tells his friend. "I'm going to have a party. There's not going to be any parents!" Unfortunately, he books the same hotel his parents are at. While Todd and Julie are enjoying some food and fun, someone knocks on their door — two exotic dancers looking for Chrisley. Julie feels extremely insulted, and Todd is completely confused — until the dancers ask if he's Chase.

Todd and Julie find their son with his friends in the hotel and immediately drive him home. While it was extremely embarrassing for him, he asks the all-important question: "Am I going to get a refund?"

No one knows you better than your kin, so why not have them pick the perfect boyfriend for you? Of course, this is what the Chrisleys did with Savannah Chrisley during Season 5, and it was exceedingly awkward. The entire family gathered around one evening to discuss who they wanted Savannah to date. Todd Chrisley even got out his whiteboard and made a list for his daughter of all his specific demands. "I want you to be with someone that you can have a future with," he told her, and obviously, "somebody that I'm going to like."

To make sure she picked the right one, he even followed her to a singles event and started talking to the guys himself. "I can find my own man," Savannah says — but not before her mom finds one first.

During their girls lunch, Julie Chrisley has invited her daughter's ex-boyfriend to come see them. Julie says he is in town, when in reality, she had him fly into Tennessee for the day to see if they still had sparks. It was even embarrassing for all of us watching from home.

The Chrisleys also try to pick the perfect someone for Chase Chrisley. During Season 6, Todd Chrisley pins up headshots on his whiteboard for the family to see. Savannah Chrisley, however, disagrees completely with his choices and decides to set Chase up with who she thinks is the perfect girl instead. Awkwardly enough, Todd and Savannah coincidentally set Chase up with both women — at the same time.

When he shows up to the restaurant, he's seated awkwardly between the two women. Did we mention that his whole family is sitting around him watching too? The poor guy even ends up being the only one not talking. "Chase normally dates blondes," Savannah finally says to Todd's brunette choice. "Yeah, well how well's that worked out for him?" Todd responds, all with his son sitting right there.  

Todd begins to quiz the two girls to make his look best, and Savannah's choice even begins talking about having Todd's grandkids. "I'm embarrassed!" Chase later admits off camera. "I expected this from my dad, but Savannah?" He eventually runs out of the restaurant, leaving the two lonely girls at the table.

When Julie Chrisley's birthday rolled around during season four, Todd Chrisley thought it would be best to throw a party — for himself. "He's planned this whole party, and he's going to be singing," Julie Chrisley explained. "Introducing himself as a country singer." It seemed like the next natural step for someone who had moved to Nashville, after all. He had Julie plan the whole thing, without letting her know it was really a surprise birthday party for her. That probably would have been nice to know. Everyone seemed to feel awkward and uncomfortable throwing their dad a party on their mom's birthday.

The real surprise, however, was that Todd was recording a special song for Julie. "I want to give her something that will mean more to her than anything I've given her materially," the millionaire said, so he hired songwriter Shane Stevens to help him out. He even brought in country singer Sara Evans for a duet.  

When Todd dropped "Infinite Love" at the party, Julie was shocked. The song ended up on the Billboard charts, and even in later episodes, Todd still likes to brag about it. We'd expect nothing less.