By the end of Friends, everyone (or almost everyone) is coupled up, married off, having babies, and generally settled down with someone to love. But it was a long road to get there, as Ross, Rachel, Monica, Chandler, Phoebe, and Joey spend a lot of the ten seasons dating all kinds of weird and wonderful people. Some of them end up as short-term flings (like Ross's relationship with the woman who couldn't clean her apartment), and some end up as pretty serious relationships (like Monica and Richard), but others don't make it past the first date.
These first dates are, in fact, some of the worst in the entire show - dates that leave the gang wondering if it's even worth dating, because the people they are meeting are just plain awful. Or, sometimes, it's the Friends crew themselves that are the terrible ones...
Monica: Chip Matthews In High School
In high school, Monica was not exactly popular, but Rachel dated the most popular guy in school: Chip Matthews. So when he reappears in their adult life and asks Monica out on a date, she is thrilled (even if Rachel is less happy about it). Unfortunately, on the date, Monica discovers that Chip is still 'Chip Matthews in High School'. He still lives with his parents, works at the movie theater where he had an after school job as a teen, and hangs out with all the same people. Needless to say, Monica was hoping he would have grown up.
Ross: The Leather Pants
This one is definitely on Ross, although fans can sympathize with his desire to change his life after a bad few years. But after he makes the commitment to try something new every day, it goes horribly wrong when the 'new thing' is wearing tight leather pants on a date. It's not the best look, but it gets much, much worse when he goes to the bathroom, and then discovers that he can't pull his pants back up! After trying talc, moisturizer, and just plain panic, he ends up having to walk out covered in paste, holding his balled-up pants in front of him. Ouch.
Chandler: Naked In A Bathroom Stall
When Chandler meets a girl that he used to know in fourth grade, at first he is thrilled - she's gorgeous (played by Julia Roberts), seems into him, and asks him out. Which is amazing, especially when she encourages him to wear lacy underwear before the date (meaning that, presumably, they will be having sex later). What's less amazing is when she follows him to the bathroom, takes off all his clothes (except the underwear)... and runs away with them, reminding him of how he pulled her pants down as a kid and embarrassed her. Chandler ends up stuck, almost-naked, in a restaurant bathroom.
Ross: Demon Teeth
This is another example of Ross being his own worst dating enemy, when he decides to get ready for a date by getting his teeth whitened. Great idea in theory, but in practice, he ends up leaving the gel on too long and his teeth end up luminous!
After everyone comments on it (and Pheobe runs away, shrieking 'demon!') he eventually just spends the whole date covering his mouth and barely speaking - which actually works well! Except that when he suggests turning off the lights, his date has a blacklight, and his teeth glow in the dark.
Rachel: How Long Do Cats Live?
When Ross was dating Julie, Rachel was struggling - but she did still try and go out to meet someone new. Sadly, this didn't work out well for her poor date, Michael, who took her out right after she learned that Ross and Julie would be getting a cat. The date begins with her distracted, and then asking how long cats live... if you run them over. She then proceeds to get impressively drunk, grabs another diner's cell phone, and calls Ross to announce to his machine that she is 'over him'.
Chandler: When Janice Was His Blind Date
Janice is probably Chandler's most-hated ex-girlfriend (although sometimes it's hard to really see why, in retrospect). Their official first date is not shown in the series, but they get another first date... when Chandler and Joey go on a double date, where the woman Joey is seeing wants to set Chandler up with her friend. The friend is, you guessed it, Janice. Finding out a blind date is a set up with an ex has to go down in worst date history.
Joey: The Roommate Problem
It's no secret that Joey dates a lot of women, and that he sleeps with most of them - but it seems that Joey has been with so many women, he can't even them all! In this instance, he meets a woman at the coffee house and they go on a date that takes them to her apartment.
So far, so good, except that Joey is sure he's been in the apartment before, and starts assuming he has slept with this woman in the past - something that she isn't happy about, especially when it turns out that he actually slept with her roommate, and forgot the face.
Monica: Paul The Wine Guy
Monica is initially thrilled that she gets to date 'Paul the Wine Guy', and it seems that her date goes well - they have a nice dinner, and he opens up to her and reveals that he hasn't been able to 'perform' since his wife left him. Monica ends up bringing him home, and is completely happy that she managed to break this dry spell... until her colleague reveals that she had exactly the same experience, and Monica realizes that it was all a lie to try and get her into bed.
Rachel: The Blind Date
ive aggressive manipulation is something that the Friends are great at - and that's why both Ross and Rachel end up being set up on intentionally terrible dates by their friends. Ross isn't actually set up with anyone, so he believes he has been stood up, but after this date, Rachel probably wishes she had been too! She goes out with the stoned restauranteur from an earlier episode, and he is miserable, negative, and inappropriate. According to her, it's the worst date she's ever been on.
Chandler: Too Many Sisters
This was a bad situation for everyone involved, though it's not totally clear if this would technically be a first date, or a second. In this episode, Chandler gets incredibly drunk at a party, and ends up making out with one of Joey's sisters... but he can't which one! So when he goes over to their house, he ends up stuck having dinner with all of them, trying to figure out who is who, and then accidentally kissing the wrong one. Yikes!