Friends: 10 Most Cringeworthy Moments

Friends set more than a few worldwide trends, from the "Rachel" haircut so popular in the '90s, to the oversized shirts favoured by many to this day. Thankfully for men around the globe, Ross' pink, patterned, women's V-neck number from the plot-heavy final season episode The One with the Birth Mother would not catch on.

Ross is initially shown arguing with Joey in Central Perk over the merits of his choice of attire, which had actually been picked out by Rachel for herself and taken by Ross by mistake, and ends with the cocksure Geller noting "See? All eyes on me!". Ross' bravado and obliviousness to the obvious problem serve as a perfect set-up for what is to come.

Said date is definitively not a success (even by Ross' standards), with his date arriving in the same top, and an immediate early end to the night called. The dumbfounded look, and subsequent swift bashful exit between Schwimmer and his counterpart is another example of his exceptional talent and flair for cringe comedy, making for a memorable enough moment to feature on this list.