The Office: 10 Times Kelly & Ryan Made Fans Cringe

Of all the relationships on The Office, Kelly and Ryan’s might have been the most embarrassing. Here are just a few of their cringeworthy moments.

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While Jim and Pam might be the most relatable and beloved love story on The Office, and even Michael gets his happy ending with Holly, Kelly and Ryan’s relationship is one of the most chaotic of any pairing on the show. These two are always dating, breaking up, and fighting, and despite being awful together, they can never seem to stay apart.

This turbulent relationship leads to some rather hilarious moments in the series, but sometimes, the laughter from fans shifts to second-hand embarrassment. These are the times when fans were cringing while watching their relationship play out.

10 When Ryan Hits On Pam

Ryan’s treatment of women was generally pretty poor, as he seemed to think he was able to date anyone he wanted and mostly only viewed women as worthwhile for their looks. So when he tried to hit on Pam, the entire sequence was cringe-worthy.

He made her believe he wanted her help with art for the company, but instead, he was really just trying to get her to go out with him even though she was with Jim. It showed his arrogance and also his lack of respect for others.

9 When Kelly Plans Their Wedding After One Date

Kelly is a rather entertaining character on the show with some memorable lines, but her dramatic personality and tendency to overreact sometimes were a bit awkward to watch.

When Ryan and Kelly hooked up on Valentine’s Day for the first time, Kelly started planning their life together. It was clearly moving too fast, and Ryan wasn’t on board for this serious of a relationship.

8 When They Constantly Argue In The Annex

While most of the employees at Dunder Mifflin didn’t have to deal with hearing Ryan and Kelly’s relationship drama play out, Toby had to listen to it day in and day out. Kelly and Ryan would argue over the smallest things, and then, they would sometimes start making out.

This would clearly be inappropriate behavior in any real-world office, but it was rather hilarious to watch. However, it was also such bad behavior that many viewers did cringe a little to see it.

7 When Ryan Implies He Should Be Able To Do Better Than Kelly

Ryan is an arrogant character who thinks he’s much smarter and important than he is. Even when he can’t make a sale or when he gets fired for committing fraud at corporate, he still maintains that he’s nearly a genius. However, this clearly isn’t the truth.

Because of his vanity, he clearly thinks he’s not good for Kelly. Often, this seems to be a slight at her looks, as well as her personality, so it was uncomfortable to watch.

6 When Ryan Gets Kelly To Break Up With Darryl

After Ryan is fired from corporate and before he returns to the show, Kelly has a brief relationship with Darryl Philbin. While Darryl was likely much better for her, she falls right back into her toxic pattern with Ryan when he comes around.

The fact that it was Ryan who convinced her to break up with Darryl and that they were making out beforehand was awkward. However, Darryl wasn’t too upset and was clearly not wanting to deal with the drama of Kelly anymore.

5 When They Announce They Got Married And Divorced

While Kelly spent most of their relationship wanting to get married and Ryan wanted to avoid this, they randomly revealed in a pre-opening credits scene that they had already been briefly married and divorced. While the fact that they wanted people to take sides was hilarious, it did seem a bit out of character.

This moment didn’t completely make sense for Kelly and Ryan, but it was still cringe-worthy to watch. They clearly wanted to involve everyone in their relationship drama, and this was one of their biggest running problems.

4 When Ryan Uses Kelly For Money

The dynamic between Ryan and Kelly is rather imbalanced, as Ryan thinks he’s better than her, and Kelly often seems to believe it. Because of this, Ryan often uses Kelly to get things he needs, such as money.

As the season wore on, Ryan became more unstable and unable to hold down an actual job, yet he still was just as arrogant. It made fans feel sorry and also a bit embarrassed for how Kelly put up with this treatment.

3 When Kelly Lies About Being Pregnant

After Ryan is surprisingly given Jan’s former job, he abruptly breaks up with Kelly in his usual selfish way. But, when he comes back for a visit to Scranton, Kelly does something possibly more cringe-inducing by lying about being pregnant.

She’s clearly trying to get Ryan’s attention, but having to lie about something like this to get it makes her look a bit desperate. It’s another embarrassing moment that shows how bad they are together.

2 When Ryan Asks Erin For A Threesome

Ryan always tries to get women to be with him in the office, and one of the most cringeworthy things is when he tries to manipulate Erin into having a threesome with him and Kelly.

It’s definitely also a moment of harassment, as he shows Erin pictures of Kelly topless without asking her permission first. Given that Kelly and Erin were friends, it also felt particularly gross of him to try and insert himself into the middle of the friendship.

1 When Ryan Ditches His Own Son

The worst thing that Ryan Howard ever does on The Office, by far, is to literally ditch his own baby with a woman that he barely knows. His neglect and selfishness are truly horrifying, and the fact that Kelly goes along with this and finds it romantic is also disturbing.

Fans were cringing and also rather disgusted with this. But, while it was extreme, it did seem like the peak level of toxicity that always existed in their relationship.

Link Source : https://screenrant.com/office-kelly-ryan-relationship-cringeworthy-moments/