Over the course of ‘Friends,’ Monica Geller had her share of affairs prior to ending up with Chandler Bing. Yet, one of those affairs was so weird and inconsiderate that it is still one of the most cringe-worthy moments in the show’s history. Which moment? When Monica slept with none other than Richard’s son, Timothy Burke.
A Strange and Awkward Situation

Monica’s affair with Dr. Richard Burke, an older ophthalmologist and close family friend, was a controversial plot point already. While they were in love, their huge age difference and differing opinions about children made their eventual breakup inevitable. But things took a downright creepy turn when Monica subsequently went out with Timothy, Richard’s son.
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The whole thing was uncomfortable from the beginning. When Timothy made an appearance in The One with Chandler’s Work Laugh (Season 5, Episode 12), it was made known that not only did he resemble his father but had equally mannered traits. This made it extremely uncomfortable for all involved, particularly Chandler, who was already feeling insecure about Monica’s past with Richard. The worst part? As Monica and Timothy kissed, she confessed that she was thinking about Richard, and the whole scenario was even more sordid.
Why It Was Totally Fubared

Monica’s tryst with Timothy was wrong for a number of reasons. One, it blurred the lines of what’s socially acceptable—dating a child of a former lover is definitely creepy. Two, it indicated that Monica hadn’t let go of Richard yet, and this was intentional towards both Timothy and Chandler. Her desire for him wasn’t genuine but rather about holding onto a previous relationship in an uncomfortable manner.
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Finally, the whole affair made Monica appear desperate and not emotionally mature. It was evident that Timothy was a rebound, and exploiting someone—especially the son of an ex—as a means to deal with unaddressed emotions was not right.
The Impact On Friends

Richard represented more than just an older man. He was also a good friend to Joey and Chandler. His membership in the group injected an awkwardness into those relationships, especially given Chandler’s attraction to Monica. Having a friend dating someone older, who the friends had even looked up to as a role model, made for some awkward moments in the dynamic. While Joey and Chandler eventually came around to accept the relationship, it set a tone of uncomfortable, unspoken tension that was never resolved.
It Undermined Monica’s Character Development

In ‘Friends‘, Monica’s character is one with a desire for stability and a future family. From the very beginning, the relationship between Monica and Richard signaled that Monica wanted to marry and have children, while Richard, having already gone that route in life, did not. For Monica to be willing to let go of a relationship-long dream also seemed counterintuitive to the strength of will that was portrayed throughout her character arcs. It made for a heartbreaking break up when their differences were finally realized, however, it also felt like an unnecessary emotional hurdle Monica had to clear.
Intended to be funny, but it actually showed just how emotionally complicated and inappropriate her decisions could be sometimes. Fortunately, it was brief, and Monica ended up with a much healthier and more loving relationship with Chandler.