Top 10 Most Embarrassing Things That Happened to Ross on Friends

Oh, Dr. Geller, when will you ever catch a break? Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Most Embarrassing Things That Happened to Ross.

For this list, we’re looking at the most humiliating and hilarious moments in “Friends” when luck just wasn’t on Ross’ side. In case you haven’t witnessed Ross’s worst moments, here is your Spoiler Alert!

#10: Making a Move on His Cousin

When a visit from Ross and Monica’s cousin Cassie goes awry after Chandler stares at her gorgeous hair, Cassie moves to Ross’s place, who’s surprised to learn that his young cousin has grown into a beautiful woman. Unfortunately, Ross finds himself smitten the same way Chandler had been, misreading Cassie’s mannerisms as attempts to seduce him. Ross leans in for a kiss, but is instead put on the spot by a scandalized Cassie. We watch as Ross tries and fails for several agonizing moments to come up with any excuse for his behavior, before landing on maybe the worst one . . . Now that’s going to be one awkward family dinner at the Geller household in the future.

#9: Wearing Rachel’s New Sweater to a Date

Remind us never to go to Ross for fashion advice. After trying on a variety of clothing options picked by Rachel to impress a date, Ross is put off by his lack of success at finding the right look. However, one particular sweater captures his interest and he’s not shy to flaunt it. Not realizing he’s switched bags with Rachel, and despite being warned by Joey, Ross mistakes the looks of astonishment from onlookers for admiration. It’s only when he sees his date wearing the exact same top that Ross understands what’s going on. By then it’s a little too late. It wasn’t all bad, though, since Ross still wore the shirt even after his date ditched him.

#8: Getting a Ticket for Driving Too Slow

We all know Ross isn’t exactly the most daring person out there, and his driving skills reflect his fearful nature. As he drives Monica’s Porsche, his miserly pace on the road invites some mocking words from Rachel. But it’s when he’s stopped by a cop that his humiliation really begins. After he’s handed a ticket for his lackluster driving speed, Ross tries to copy Rachel, whom he’d seen flirt her way out of a similar situation earlier. Unfortunately for him, Officer “Pretty” isn’t in the mood. Ross is left not only with a ticket for driving too slow, but also with no self respect.

#7: Having a Fake Memorial Service with Nobody Showing Up

When Chandler writes on their college alumni site that Ross gets down and dirty with dinosaurs, it starts a prank war that leaves their classmates believing that Chandler is gay and Ross is dead. While Ross initially scoffs at Chandler's prank when there are no responses, he’s dismayed to realize his former classmates care more about Chandler “coming out” than his supposed demise. To make matters worse, when Ross makes Chandler host a memorial service for him, only two people show up. And one is a potential suitor for Chandler! When an attractive former classmate does arrive to pay her respects, Ross reveals the charade in excitement, which doesn’t go so well...

#6: His Cringeworthy Flirting

When his friends make fun of him for his poor flirting skills, Ross decides to prove them wrong by hitting on the cute pizza delivery girl Caitlin. However, rather than coming across as the suave, cool guy he wanted to, Ross starts off by forgetting her name, and can only come up with terrible wordplay. His friends watch in embarrassment as Ross then dives into trivia about different kinds of gas. As his flirting becoming increasingly worse, Caitlin flees without taking her payment. It’s then up to Rachel to convince her how great Ross is as a boyfriend. Hey, at least Ross did manage to interest Phoebe in his gas trivia.

#5: Not Chipping In for the Handyman

Talk about making a bad first impression! While Ross is celebrating getting Ugly Naked Guy’s apartment, he’s asked by his neighbor to chip in $100 for the departing handyman in his building - even though he’s just moved in. Ross refuses to contribute . . . but when he finds out that everyone in the building now thinks he’s cheap, he decides to throw a party to show them he’s a nice guy. After nobody shows up, however - and even Phoebe joins the handyman’s going-away party instead - Ross sneaks a slice of the handyman’s cake. Naturally, he’s caught and put on the spot. When Phoebe tries to turn things in Ross’s favor, they both end up getting kicked out.

#4: The One Where He’s “Fine”

In this instance, Ross’s embarrassment is all his own doing, after he denies his feelings about Joey and Rachel’s romance. After walking in on Rachel and Joey kissing, Ross insists he’s “fine” for the rest of the episode. However, his antics, including talking in a high-pitched and squeaky voice, drinking all the margarita, and using a hot plate without gloves, gives away that he’s not actually “fine” at all. To top it off, Ross also gives an elaborate toast to “love”, where he goes into painstaking detail about the meaning behind each letter. The following morning, he’s left to rue his behavior, in rather painful ways.

#3: Kissing His Own Sister

At their college reunion, Chandler confesses he kissed Rachel when he found out that Ross had broken their pact to not get involved with a mutual crush. Upon hearing this, Ross takes the news hard, thinking it was the night he’d kissed Rachel for the first time. However, upon recollecting events, Chandler informs him that the girl he’d left on Ross’s bed hadn’t been Rachel, and Monica’s revolted response confirms who Ross had kissed instead. Having confessed to the kiss being “amazing”, Ross is horrified to learn that not only did he once kiss his own sister, he actually liked it. At least Chandler had the appropriate response for this revelation: [Chandler asks what he married into]

#2: Getting Stuck in His Pants

Not only does Ross have bad luck with shirts, he doesn’t fare any better with pants. As part of his New Year’s resolution to try something new every day, Ross tries on a pair of tight leather pants. This comes back to bite him, though, when he can’t get them back on while in the bathroom during a date. Calling Joey for help only makes things worse - leaving him covered in powder and lotion. Admitting defeat, he steps out without any pants at all. The fact that Ross then had to walk all the way across the city in this state to Monica’s apartment makes it even more hilarious.

Before we unveil our top pick, here are a few honorable or in this case embarrassing mentions.

Saying the Wrong Name at the Altar

Falling into an Open Grave

Stuck Between Mona & Rachel’s Dad

Ross’s “Sound”

Almost Getting Outed by Phoebe

#1: Getting a Tan

Jealous of Monica’s tan, Ross heads to a tanning salon. Unfortunately, failing to count “Mississippilessly” means that Ross is too late to change sides once he’s sprayed, resulting in a way darker complexion than he’d wanted. It doesn’t get better in later attempts either, as Ross continues to be confused and gets sprayed on the same side over and over. When he tries to tell his friends about it, all he gets are some hilarious jokes from Chandler at his expense. Once the tan sets in, an unrecognizable Ross attempts to hide himself at home, but still can’t escape Chandler, who ensures none of their friends will ever forget Ross’s greatest embarrassment ...