Friends: 10 Most Cringeworthy Moments

Tom Selleck's appearances as Monica's love interest Richard Burke in the earlier seasons were a great addition, a more serious dramatic presence for the younger cast to bounce off, he would significantly enhance the "sit" in sitcom. Sadly, we would see Selleck leave the series as a consistent presence in Season 3, and only return for a few cameos from Season 5 onwards.

For all the good the character brought to the show, it is marred by a particularly cringeworthy later subplot. In 1997's The One with Chandler in a Box, Monica finds a Thanksgiving date in the form of Timothy, a young doctor who treats her for an ice-related eye injury.

Great, right? The only issue being that he is revealed to be Timothy Burke, Richard's son.

In one of the more self-aware moments in this list, the awkwardness of a kiss shared between the doctor and an eye-patched Monica is fully acknowledged, with the character leaving never to be seen again.

Intriguingly, Courteney Cox herself would later remark that this is the only one of Monica's relationships that she wishes the writers had let develop over a longer period of time.