Charlotte Flair has been one of the most dominant WWE Superstars of her generation, and throughout her run she has been booked to look fantastic. Her performances have always been strong inside the ring and on the microphone, which is why the company has consistently put her in main event opportunities.
However, while she has been involved in a lot of memorable storylines and moments, there have also been plenty of situations that have left fans cringing as they watched them. Whether this was because the writing was poor, the delivery didn't make sense, or mistakes were made, even the Queen has been in some odd situations over the years.
10 Partnership With Dana Brooke
A lot of people forget about the partnership that Charlotte Flair had with Dana Brooke, and that is with good reason - it was poor. Brooke had been brought to the main roster and WWE clearly wanted to push her at points, which is why she was placed alongside Flair.
However, Brooke simply wasn't ready to be working at that level, and anytime they ended up working together that was obvious to see. It led to plenty of cringey moments that didn't work, with the entire partnership not being a good moment for her.
9 Ric Flair Celebrates With Her Opponent
Everyone knows that Ric and Charlotte Flair have a close relationship, and that has led to some great moments between them on-screen, where their chemistry has always been clear to see. However, when Flair was defeated by Sasha Banks after their Falls Count Anywhere match, the Nature Boy took a strange turn.
Rather than being disappointed his daughter had just lost the Raw Women's Championship, Flair opted to hit the ring and celebrate with Banks, which was an odd call considering the fact Flair lost.
8 SummerSlam Botch
Charlotte Flair is a great worker and someone who puts together fantastic matches regularly, but even she is capable of making mistakes every now and then. That took place during her SummerSlam 2016 match against Sasha Banks when she ended up dropping Banks down to the top turnbuckle.
It was a rough landing for the Legit Boss and was one that could have ended up leading to a serious problem. Thankfully, that wasn't the case, but it was a cringey moment for Flair's career.
7 Pie To The Face
The idea of Charlotte Flair feuding against Toni Storm is something that a lot of fans were excited for considering the fact they are two extremely talented in-ring workers. However, when WWE ended up putting them together things didn't quite work out in the manner that people expected.
Their segments ended up being cringeworthy to watch, as everything ended up being booked around Flair throwing pies into Storm's face. It was a strange situation and was something that fans didn't enjoy overall, mainly because there was nothing serious for them to connect with.
6 Her Father & Lacey Evans
Before Lacey Evans took time away from WWE due to being pregnant it was clear the company was heading in the direction of her feuding with Charlotte Flair. However, the manner in which they were attempting to do that proved to be rather cringeworthy to watch from an audience perspective.
While the company never committed to properly saying it, the entire situation was insinuating a relationship angle involving Ric Flair and Evans, which was painfully awkward to see unfold on a weekly basis.
5 Table Bumps Don't Work
When Charlotte Flair and Sasha Banks met inside Hell In A Cell, the pressure was certainly on. This was the first ever female Hell in a Cell match, therefore the two women wanted to go all out and put on an iconic match. While they had many great moments, the match did feature a couple of cringey mistakes.
Flair tried to put Banks through a table several times during the match, but at no point did they break. Because Banks is so light, Flair needed to put a lot more pressure on, but when it didn't work on more than one occasion, it ended up falling flat.
4 Contract Signing Disaster
Contract signings are common in the world of professional wrestling, and they always end up being physical in some form, which was the case when Charlotte Flair and Sonya Deville teamed up to face Ronda Rousey and Naomi. The promos were fine but nothing spectacular, but they weren't the problem.
Things became cringey when physicality was added to it, as Rousey attempted to smash Flair's head down into the table. For some reason she completely no-sold the situation, stopping short of the mark which made the entire segment look horrendous.
3 Taking A Twist Of Fate
Whenever a legend returns to wrestling, the chances are always high that they will be made to look good in the moment, which was the case when Lita and Charlotte Flair had a segment together on SmackDown. Lita was able to hit the Twist Of Fate, dropping Flair to stand tall.
However, while Flair is normally brilliant inside the ring, this particular night was not the case. The way she took the move was incredibly awkward, and it was clear she wasn't comfortable with the bump, which hurt the entire segment.
2 Charlotte Flair Vs. Nia Jax
While Charlotte Flair and Nia Jax are friends now, there is no doubt that the match they had on Raw in August 2021 was cringey to watch. It appeared that both women were shooting in that one, putting in some physical moments that made things look like a fight.
But it wasn't a natural fight with an aggressive tone like some of Flair's matches against Ronda Rousey or Becky Lynch. Instead, this one was awkward and clunky, and it felt like they were not on the same path at all, which was strange to watch.
1 Charlotte Flair Added To WrestleMania 35
Charlotte Flair being in the first ever women's main event at WrestleMania is something she certainly deserved, however the way WWE injected her to the match between Ronda Rousey and Becky Lynch was cringey to see. Vince McMahon simply came out and made it happen, with nothing else to it, which was odd.
Flair herself has admitted to not liking how that was handled, and that was the belief that the WWE Universe had as well. It came out of nowhere, and it was strange to see because of that.