Dating in your 20s and even 30s is a tricky business. Especially for the characters in Friends. Over the course of the show, fans have seen their fair share of bad dates and not-so-well-liked exes. Not to mention the many flirting attempts that are either smooth sailing or had fans cringe.
Compared to the male characters, Rachel, Monica, and Phoebe had better luck in this department. It wasn’t often that Phoebe’s witty and quick pick-up lines didn’t impress a cute guy. For Monica and Rachel, there was some hazardous flirtation that didn’t bode well and it showed. At least Monica found her prince charming in Chandler and no longer had to endure flirting in New York City.
10 Phoebe: Seducing Chandler
Monica and Chandler didn’t expect Phoebe and Rachel to find out about their secret relationship. It’s a memorable episode when Phoebe discovers them getting it on while looking out Ross’s apartment window. Rachel and Phoebe get some payback and have Phoebe pretend to find Chandler attractive.
To be fair, this flirting is some of Phoebe’s best work. It’s more the circumstances that make it awkward. In one scene Phoebe tries to compliment Chandler’s muscles. Later on, even she’s weirded out when letting Chandler know she wants to have sex.
9 Rachel: The Yeti
In “The One with the Yeti,” Monica and Rachel get scared by a bearded man in the storage of their building. Rachel later learns it’s their neighbor Danny, but this time he’s clean-shaven and handsome. For a couple of episodes, Rachel tries to catch his attention.
In episode seven, she plays it cool when he invited her and Monica to his party. She says she has an important gala to attend, but Monica has no idea what she’s talking about. Rachels’ attempts at acting coy do not affect Danny whats so ever.
8 Monica: The Bus Boy
Many remember season 3 of Friends for the many downfalls in Rachel and Ross’s relationship. In episode 12, Monica starts to fancy her coworker, Julio at the diner. She doesn’t exactly play it cool when he charms her with his smooth words and poetry. Monica finds a book on the counter and Julio admits it’s his.
He asks her if she’s ever read it and she tries to act cool by having him think she does but comes clean that she doesn’t. Julio then tells Monica he can write about anything even her lips. Monica is floored and as he lightly caressed her lip she goes, “How would that go.” Like a deer stuck in headlights.
7 Rachel: Her OBGYN
By season eight of the show, Rachel is pregnant with Emma. When she visits her doctor, she’s smitten with his good looks. She comically tries to learn more about him like what he does for a living, but the answer is pretty obvious. The doctor tries to get on with the examination and asks if she’s uncomfortable.
Rachel answers that she’s very comfortable and tries to be bashful when he asks if she has painful gas. The doctor asks if Rachel would like to lie on the table, and she wittily says, “Would you like me to lie down on the table?” The doctor then gets a bit weirded out at her advances.
6 Rachel: Soap Opera Star
Fans of the show know that Rachel is a huge soap opera fan. Joey finally takes her to work and she gets to meet her dreamboat actor. But being so lovestruck with meeting him, her flirting doesn’t go so well. She tries to not sound like an obsessive fan but fails miserably.
She even tells the actor that she knows his favorite ice cream flavor. The awkward encounter still works as the actor told Joey he found Rachel charming. But sadly the date doesn’t go well.
5 Monica: Strip Tease for Chandler
Monica makes a mistake when she accidentally hires a hooker for Chandler’s bachelor party in season eight of Friends. After the disastrous events that occur, Monica tries to make it up to Chandler. She puts on her own show to flirt and seduce her future husband.
With music in the background, she takes off her jean jacket but it gets caught. She then narrates her next move. Monica exclaims in a sexy voice that her tennis shoes are so tight. The scene isn’t exactly her best. Even Chandler asks her to stop narrating.
4 Rachel: Dressing Room With Joshua
Rachel has a new crush when Joshua walks into her job in season four of Friends. So smitten, Rachel blurts out things she shouldn’t say. When Joshua wants to see clothing options she blurts out, “Let me show you my underwear.” At a later appointment, she tries to hint that she’s single and available.
Rachel continuously gets flustered when trying to flirt with Joshua. While trying to ask him out to a basketball game, she completely forgets to mention that the date is with her. Even when he asks for some leather gloves, Rachel tries to flirt by saying he’s a size large.
3 Monica: Flashback To Weight Loss
In season five of the show, the characters recount their Thanksgiving memories. One being where Monica loses a lot of weight because of a comment Chandler made. Monica’s weight loss is a shock to Chandler and he finds her attractive. In the kitchen, Rachel comes up with a plan to get revenge on him.
Monica has to try and seduce him and then completely ignore his advances. It doesn’t go well as Monica isn’t the best flirt yet. She even puts carrots in between her fingers and looks like Wolverine. Monica also tries to seduce Chandler while rubbing a box of pasta on herself.
2 Rachel: Emily’s Impromptu Party
Rachel’s journey to try and impress her new crush Joshua doesn’t do so well. In episode 16 of the fourth season, Rachel comes up with a plan to host a fake party so she can invite Joshua. She tries to impress him by tying a cherry stem with her tongue but ends up choking.
In an attempt to get a kiss, they play spin the bottle, and Rachel lands on Joshua. Phoebe ruins the opportunity when she feels the baby kick. Rachel doesn’t give up and brings out the cheerleading uniform but again gets another failure. Her last attempt is to try and remove her bra.
1 Monica: Sick Flirting
Monica hates the idea of being sick, and rejects it completely. But in episode 13 of the sixth season, Monica gets a bad cold. So determined to not look or act sick, she tries to seduce Chandler. The runny and stuffy nose doesn’t help as she says her popular line, “In the pribe of libe.”
The coughing and phlegm turns Chandler off for obvious reasons. She later lights some candles in the bedroom and pages Dr. Bing but gets a bad case of chills. But Monica actually succeeds when she rubs menthol gel all over her chest in front of Chandler. It might have been the rubbing or the smell that won Chandler over.
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