For most, the iconic high school dance is one of the most unforgettable moments of the entire school year. Prom-goers shiver from anticipation and hope to leave with some of the best memories from teenage life. But if you look back to that crazy night and cringe with nostalgic discomfort or think back on your wardrobe choices with a bit of a shudder, you're definitely not alone.

So this recent challenge on The Tonight Show was all about the funniest and weirdest #PromFail moments. Jimmy Fallon kicked off the thread himself by tweeting: "My friend ripped his tuxedo and spent the night crying because he thought Men’s Wearhouse was going to sue him." But it seems that people on the Twittersphere have had it way worse. I mean, we’re talking about being named the "condiment couple" or being crowned as the Prom Queen yet having to slow dance with the King who turns out to be your twin brother. Pretty odd, right?

After all, prom is notorious for being the perfect ground for things to go terribly wrong. We all remember how hard our own teenage years were, so just imagine having a school full of overly excited youth — there’s bound to be no shortage of mortifying moments. Moreover, they sometimes expect too much from this celebration and often label it as the most important night of their young lives, something that’s hard to live up to.

According to columnist Claire Suddath, the word prom is short for promenade — the formal, introductory parading of guests at a party. The prom can be dated back to the simple banquets that happened in the 19th-century American universities to celebrate each year's graduating class.

"A growing teenage culture pushed proms younger and younger, and by the 1940s, the adolescent dance we know today had almost entirely taken hold," Suddath added. With time, every generation continues to improve and change our society, and that in turn leads to proms becoming more eccentric each year. As customs change, we see an increasing amount of extravagant limousines, creative themes, colorful wardrobes, and teens trying to make this celebration represent what they believe in.

As you’re scrolling through this list, you’ll notice that no one is immune to occasional slip-ups on this big night. Some teens feel extremely worried about this iconic dance and may fear creating situations that would be the perfect material for the next #PromFail challenge. To avoid that, parents can also help out their children with handling the many stresses and challenges.

Amber Olson, a licensed clinical social worker, explained that parents can play an important role in how teens experience their prom. "Ask your teen about what they want from their prom experience and then help shape healthy expectations for the evening," she suggested.

That includes considering several elements your child might be slightly obsessing about. For example, you could set a realistic budget for the apparel and the extravagant "promposals". Or discuss your teen's feelings about their potential date or the celebration in general. You could also sit down and have a chat about unhealthy diets or extreme workouts your teen may do to lose some weight. "These short-term gains can lay the groundwork for long-term unhealthy eating habits and poor body image," Olson said.

"Role model for your teen the importance of being present in the moment and encourage them to stay mindful as they take in all the details of the evening," she added.