One of the aspects of Friends that is enjoyable to watch is watching the characters try to flirt with a cute girl or guy. It didn't always go as planned and sometimes left the characters making a fool of themselves. Fans can agree that Chandler, Ross, and on some occasions Joey, would bomb at attracting the opposite sex. To be fair though, somehow Joey's "How you doing?" always seemed to work.
Fans wouldn't argue that Ross and Chandler are the characters who were the worst at flirting, and many memorable attempts had audiences laughing and cringing. But being in your mid-to-late 20s and living in New York City can make for a complex dating life.
Joey: When He Tried To Flirt With The Casino Worker In Las Vegas
In season five of Friends, Joey gets duped to star in a movie that gets shut down. Unwilling to admit his failure to his friends, he stays in Las Vegas working at a casino, where he meets his hand twin. When Joey goes to talk to him, the worker isn't at his table.
Joey asks the worker who took over his shift and learns he went to the bathroom. But, of course, Joey had to try and put his moves on the pretty female. He uses his iconic line, "How you doin'?" But the worker is indifferent to his advances and simply answers, "Very busy." Joey quickly gets the memo and walks away.
Ross: When He Thinks Rachel Wants To Get It On
When Chandler, Pheobe, and Monica go ahead first to Las Vegas, Rachel gets some alone time in the apartment - a very rare opportunity. Like anyone would do in her situation, she dances around naked. Rachel is unaware that Ross can see her from his apartment, He ridiculously thinks she's inviting him over to "do the deed" and so he heads over.
When she opens the door, Ross makes a horrible attempt at sounding suave and flirtatious. He leans against the door giving Rachel a "flirty" look and says, "Hey." He then proceeds to ask if he can come in, but Rachel is weirded out and says if he wants to, he can. He tries to sound cool and then says, "Do you want me to?" Rachel then learns that Ross can see her and he learns that she wasn't trying to lure him over.
Ross & Joey: When They Try To Use A Baby To Attract Women
It wasn't often that the guys babysat Ben. But Ross didn't have a choice in season 2 when he has an allergic reaction to kiwi. Joey assures Ross that he knows how to take care of Ben and while waiting outside, Joey tells Chandler that babies attract women.
But their first attempt at flirting doesn't go well, seeing as the woman thinks Joey and Chandler are a couple who just adopted the aby. They catch the eyes of two other women boarding the bus and tag along. Afraid that these women will also think that they're a gay couple, Joey tries to emphasize they're straight "manly men." They then get off at the women's stop and forget Ben on the bus.
Joey: When He Flirts With The Staff During The Twin Study
Joey isn't making enough money working at Central Perk and he's not getting enough work as an actor, so he decides to, again, take part in some medical experiments for some cash. This is the same as in the season six episode with Ross's "unagi."
At the hospital, Joey is too late to partake in any experiments, but he learns there's a twin study worth $2,000. Joey hatches a plan and tries to flirt with the worker and says there's a new study available about testing the effects of Joey Tribiani on an attractive nurse. The nurse tells him they already got the results back and they're not looking so good. Ouch.
Ross & Chandler: When They Flirt With The Two Women At Central Perk
By season nine of Friends, Monica and Chandler are already married, meaning that Chandler shouldn't have to go out of his way to embarrass himself by flirting with women. But Ross convinces him to try it out like their old college days in order to make Rachel jealous. While at Central Perk, Ross spots two women and Chandler tries to break the ice with a joke about a human pyramid, which makes Ross swoop in.
Ross tries to sound smart about a flood in Europe and asks if they'd rather drown or be burned alive - not the best strategy to appeal to women, and their attempt epically fails.
Chandler: When He Tries To Flirt With Phoebe
Chandler and Monica's secret relationship was a huge storyline in season five of Friends. While Rachel and Joey are aware, Phoebe finally finds out. But Rachel and Phoebe decide to mess with the couple as payback and she pretends to find Chandler attractive and tries to woo him.
While Phoebe is an expert in seduction, Chandler ... not so much. Monica and Chandler figure out the plan and Chandler tries his hardest not to be freaked out by Phoebe's advances, trying to act aloof and cool. It all backfires horribly, as neither can imagine themselves ever being intimate in any way, and Chandler then admits he's in love with Monica.
Joey: When He Flirts With His New Roommate
There aren't many examples of Joey's flirting attempts failing, but it was a surprise for fans when Joey gets a new female roommate who is immune to his charm. Joey is smitten, but he is frustrated that he has expended so much flirting energy and yet his new roommate isn't interested in him.
They have a talk when Janine realizes something is off and she tells Joey that she doesn't see him in any sexual or romantic way. Joey thinks it's because he was trying to repel her and so turns on his charm. His iconic line is ineffective, however, and she says she's "doing alright."
Chandler: When He Gets Stuck With A Model In An ATM Vestibule
Chandler's initial flirting attempts don't go so well, but many fall for this sweet and comical demeanor. In season one of Friends, Chandler gets stuck in an ATM vestibule during a blackout. He soon realizes that the other female stuck with him is Jill Goodacre, the model.
Chandler can't muster up the courage to flirt with her, but when he does finally try, it's not smooth sailing. He has an inner monologue trying to hype himself up. He manages to smile at her but only ends up creeping her out. When she offers him gum, he blurts out "is it sugarless?" He even tries to look cool spitting it out but fails and ends up eating someone else's old gum. Thankfully, they do end up talking, but he never gets her number.
Ross: When He Flirts With A Cop
Ross has had some bad moments, but nothing tops him trying to flirt with a cop. Rachel and Ross are driving on the highway in season seven, episode 22. Rachel initially gets pulled over for driving recklessly, but she manages to flirt her way out of a ticket. Ross being Ross was more than happy to let Rachel take the passenger seat.
In a turn of events, a male officer then stops Ross for driving too slow. Ross does the unimaginable and tries to flirt with the cop, as well. To many viewers, the idea didn't make much sense. Ross gives him googly eyes, pretends to twirl his short hair, and compliments the officer, but the officer wasn't fooled.
Ross: When He Flirts With The Pizza Delivery Girl
One of Ross's more infamous moments on Friends was when he learned that he's not good at flirting. The episode is even titled, "The One Where Ross Can't Flirt." The gang order pizza and Chandler unintentionally flirts with the cute delivery woman. Ross tries to show everyone he is just as good as anyone else at flirting.
He keeps placing orders so that the delivery woman can come back. But every time, he fails terribly, even making a bizarre remark about her short hair being like a boy's. He even tries to inform her about gas and how it is odorless and given a smell to help one identify a gas leak. By the end, he doesn't win her over, but Rachel convinces her to give him a chance.