Friends: Chandler’s Worst Attempts At Flirting

The men of Friends aren’t exactly known for their flirting skills, but Chandler is definitely the worst of the three. Ross is consistently terrible (telling the pizza delivery woman that he ‘likes eight-year-old boys’ being potentially his lowest point) – yet somehow, he still manages to get three women to marry him. Joey is played up as the ladies man of the group (a low bar), but he seems to rely purely on good looks and ‘how you doin’. And Chandler? Well, Chandler is hopeless and awkward and desperate for love.

This doesn’t stop him at least attempting to flirt, though. In fact, Chandler occasionally shows some talent at talking to women, such as when he’s talking to that same pizza delivery woman, and is chatting casually, or when he makes a woman at a sleep clinic crack up when he introduces himself by very obviously pretending to pick up a magazine near her, just to toss it straight back down and say hello. He may have his good moments, but these ten are definitely his worst.

10 The Answering Machine Message

In ‘The One With The Evil Orthodontist’, Chandler goes on a date with a woman named Danielle, and describes it as one of the most perfect dates in the history of mankind… which leaves Monica and Phoebe appalled when he says that he’s not about to call her after it, because that would make him look needy. In the end, he is convinced to call, but when he gets her answering machine, he proves that he is utterly incapable of flirting in a recording. The message he leaves (which takes two hours to perfect) just says to give him a call back, but includes some dish-rattling sound effects, in a weird move to try and convince her that he has a life, and hasn’t been sitting around honing that message for two hours.

9 This Is Bob

In ‘The One With Five Steaks And An Eggplant’, an unknown woman named Jade leaves a particularly sexy message on Chandler’s answering machine – but it’s not for him, it’s for ‘Bob’. Chandler being Chandler, he actually picks up the phone later, and pretends to be Bob, faking a ridiculous deep voice and pretending to be smooth, so he can ask her out, have ‘Bob’ stand her up, and then swoop on in. It’s a pretty terrible attempt at flirting, and a terrible plan to lie to her, too – one that backfires, when she leaves another message telling ‘Bob’ how this guy she met was nothing compared to him.


8 We Only Need Six More People For A Human Pyramid

After Monica and Chandler get married, he is mercifully off the hook for flirting… until Ross asks him to act as wingman at Central Perk. Ross is feeling miserable about Rachel moving on, and asks Chandler to help him hit on two women in the coffeehouse – with Chandler breaking the ice with a joke, so Ross can then ‘swoop in’. Sadly, the icebreaker Chandler chooses is a total fail, as he opens with ‘Hey, if you are up for it, we only need six more people for a human pyramid”.

7 Did You Fall High?

When Chandler meets Ginger, he’s waiting outside the men’s room in Central Perk, increasingly frustrated. So when the door opens, he starts to curse out the person leaving for taking so long, but when he actually looks up, he sees that it’s not some random guy… but a gorgeous woman.

He manages to switch it up on the spot, from asking ‘what, did you fall in there’ to ‘hi!’, then realizing how ridiculous it sounds, and repeating himself… ‘So, did you… did you fall high?’. Kudos to the guy for brazening this one through.

6 Chasing Down Kathy

When Joey is dating Kathy, Chandler is actually trying very hard not to flirt with her, despite the fact that he is crazy about her, because she’s Joey’s girlfriend. This doesn’t stop him from straight-up chasing her down while jogging, though! When he sees her jogging, he waves to say hi, and calls her name, but with her headphones in, Kathy can’t hear him. And what starts as a fairly normal attempt to get the attention of a friend (jogging toward her and calling her name, waving) ends up in him sprinting after her, knocking things over, and finally reaching her completely out of breath… and then realizing how ridiculous his behavior has been, and sheepishly just saying hi.

5 I Dropped My Ball

This could have been a move that worked, but Chandler just doesn’t have any luck. In a flashback episode, it’s revealed that Chandler and Rachel nearly slept together when they bumped into each other back when Central Perk was a bar. Chandler was playing pool, and overheard Rachel saying that she needed to have sex with someone before her wedding, and that she would just sleep with the next guy she meets. Chandler, of course, decides to make sure he is the next guy she meets, and tosses the cue ball at her feet before sauntering over to pick it up with the less than phenomenal line ‘I seem to have dropped my ball’. Rachel is, unsurprisingly, unimpressed.

4 We’re Having Second Thoughts About Our Copying Needs

Chloe, better known as ‘the girl from the copy place’, appears in only one episode ‘The One Where Ross and Rachel Take A Break’. In it, she ends up sleeping with Ross, causing one of the most iconic couple fights in sitcom history, but the reason that Chloe and Ross even meet in the first place is that Chloe is out at a club with Chandler and Joey.

Their attempt at picking her up is laughable, though. First, they head to the copy place multiple times in a day, and keep pretending to just have ‘copying needs’… that can only be dealt with when Chloe is available, not her male colleague. It’s so obvious he even calls them out on it publicly, but Chloe doesn’t seem to mind, funnily enough.

3 They Don’t Know We Know They Know

This may be one of the funniest flirting scenes in the series, as both Phoebe and Chandler attempt to ‘seduce’ each other, and neither of them actually intends to succeed. Instead, they are trying to force Chandler and Monica to reveal their relationship (successfully, in the end)… and it takes longer than anyone is happy with. The awkwardness builds from the moment Phoebe steps through the door, as she dances ‘for him’ and they have the most stilted, quasi-‘sexy’ interaction on the entire show. And of course, fans love that it ends with Chandler telling Monica that he loves her.

2 Chandler & Aurora

Chandler is known for his painfully low self-esteem, and this is the most obvious when he attempts to ask out Aurora, a beautiful woman that happens to be at one of Joey’s plays. They actually end up having a short fling, but no thanks to Chandler’s attempts to get things going! Instead of just asking her out, he walks over and stands silently in front of her for a moment, before finally stuttering out a ‘hi’ and then ‘would you like to go out with me sometime? Thank you, goodnight’ and immediately walking away. Thankfully, she actually calls him back to say yes, but he was willing to let it go before even waiting for an answer!

1 Gum Would Be Perfection

During a massive, citywide blackout, Chandler finds himself trapped in an ATM vestibule with none other than Jill Goodacre, a Victoria’s Secret model. He’s obviously completely intimidated, and struggles to find any way to talk to her that isn’t ridiculous. He fails, of course, and when she offers him gum, he tells her ‘gum would be perfection’. He then manages to make it worse by trying to blow a bubble, accidentally spitting it out instead, trying to pick it up again… and picking up someone else’s old gum, instead. Poor Chandler – at least she seems able to overcome his strangeness, and by the end of the blackout they are actually having a fun time.

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About The Author

Rose Graceling-Moore (1516 Articles Published)

Rose Graceling-Moore has been writing about film, TV and comics since 2013, when she began writing for a local print magazine in Vancouver, BC. Since then, Rose has written for Horror Honeys, Moviepilot and Quirkbooks as well as Screenrant, increasingly focusing on comic books and live-action comic adaptations, as well as diversity and representation on screen. Rose also co-hosted the DC Movies Podcast, and has guested on other nerd and entertainment podcasts over the past five years.

Rose’s love of comics began all the way back in the early ‘90s, when she discovered the X-Men while living in Africa (where there wasn’t a whole lot to do but read!), and since then has had an on-again, off-again love affair with not just Marvel, but DC and indie comics as well. You can follow her on Twitter: RoseMooreWrites for tweets about comics, movies, and more.

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