I've been watching Friends for the umpteenth time and wow, these characters continuously date people they really, really shouldn't. Over and over again too, the poor choices continue from season one consistently into season ten. For the sake of this list, I only included those not in the immediate friend group, so no Ross and Rachel, Joey and Rachel, or Monica and Chandler.
Making this list made me realize two things: one, these guys never gave up; they were going to find love even if it ripped them apart and ruined other aspects of their lives, and two, they're moronic.
Here we go, chronologically, or as close as I could get without research...
Janice
I mean, I had to start with Janice. She's the only guest star to appear in EVERY season (minus six, but we hear her voice). She loved dating Chandler Bing, expressing her shock, and being difficult to dump. Janice was really great for Chandler in some ways: she understood his eccentricities, never attempted to change him, and always tried to get along with the other Friends even if they hated her (and Joey really did hate her, he even went to far as to say, "I wish I could pull off my own arm just so I had something to throw at her," yet that didn't stop Janice instating "Joey and Janice's Day of Fun.") The real problem in this relationship was Chandler. He'd be drawn to her again and again because while being the single most annoying person in New York City, she was still sweet underneath it all and meant well. She never did anything to hurt Chandler, though he lied to her and pretended to move to Yemen... Thinking about it, Chandler was a jerk to her, as he was to most of his girlfriends by the end. He was afraid of his own happiness and after immediately assuming he should probably be miserable - he'd end it, breaking other's hearts almost as often as he crushed his own.
Paolo
So I hated this guy as much as Ross did because look at his face. And his hair. And his being with Rachel when she's supposed to be with Ross. Terrible, everything about him is terrible. I think he was supposed to have this sex-factor that I just didn't understand. He had an accent and all but that really just made him harder to understand. We all know Rachel only spent time with this guy to get over her failed engagement. She'd have some meaningless sex and then she'd get out. Except the asshole hit on Phoebe and hurt Rachel anyway. She actually got hurt more than she did the hurting, which is surprising because she appears so bubbly and fun and heartbreaker-y. Nope. She might actually be the most sentimental of the group. I'd say Ross is the biggest failure in the dating game, but that might just because he had more relationships than anyone else so he was set up to fail more often. Regardless, Paolo served his purpose and then was taken away from us and we smiled and waved him off the screen.
David
David was for sure one of my favorites of all the significant others and he only dated Phoebe for a week, then he headed off to Russia for some science thing, which was rude. They got along so well! With her super weird hippie-ness and his even weirder scientist-ness, it was like a match made in super weird heaven. I really don't have anything negative to say about this pairing except that he left and she had to move on, which was a bummer. I don't know how they would have played out over the years, but it was definitely fun while it lasted. Primarily, I'm impressed I even cared because it was so short lived. Usually, no one cares about the dude that shows up for ONE episodes and then leaves for seven years. Seriously, you guys, he was in one episode in season one and that's it. We all just fell in love with him the way Phoebe did and thought it was an epic romance. God, this guy was awesome.
Kate
I won't bore you with much about Kate. I really only included her because she represents the first time Joey actually cared about a woman. So he obviously chose a really self-obsessed one that was unavailable. They have a few great nights but mostly just fought. He pined a lot and she avoided a lot, though the big struggle remained with Joey's belief he could help or fix her in some way. He obviously couldn't, which I guess is a lesson we all need to learn, so at least he finally did while simultaneously getting his heart trampled on. Poor baby, though, serves him right for falling for a rude, crazy actress. What did he expect?
Fun Bobby
Another dude that we really only met a couple times, but he sticks with the most avid Friends fans purely because they all loved him so much. He loosened Monica up, which was always nice to see but really, he loosened everyone up. This ends up being because he has a drinking problem and is always (and I do mean always) drunk, so once she sobers him up - he's not so fun. Monica overcompensates by getting drunk herself, but he says he can't be around someone who doesn't take his sobriety seriously. This doesn't sound funny as I type it, but I promise you, it's all hilarious and everyone parts ways and gets healthy. Plus, look at his floppy hair.
Julie
UGH. Go away, Julie. There's really nothing wrong with you, but Rachel FINALLY realized she wants Ross too and then you show up. Yes, we could blame Ross but this is TV and that's not how it works. All the blame falls squarely on your shoulders. She's actually good for Ross and interesting and sweet, but completely in the way. They almost get a cat together, that's how serious this thing was, but ew. No. Ross found out about Rachel's new feelings and bye-bye, Julie. Nice to know you. Sort of.
Richard
Well. This is Tom Selleck. The character of Richard almost doesn't matter because he's played by Tom Selleck. I really could have been okay with Richard and Monica ending up together. Their break up rivals Ross and Rachel's because it was for a real reason. There weren't any fights and no one stopped loving the other, but Monica wanted to be a mom and Richard was already a grandfather. This is the only time their age difference becomes an issue, but it was an unavoidable one. How depressing. Watching Monica post-break up was sad. She was basically the shell of a person, but she got over it just in time to have some more sex with Richard. This was of course stupid, but who hasn't rebounded with the source of your misery before? It happens. She gets over him again and moves on for real despite how perfect they are for each other on (basically) every level.
Janice
Because yeah, this happens again.
Pete
Pete was a weird one. He's a billionaire that falls for Monica when he meets her while she works at a Diner. She keeps turning him down over and over again until he buys her a restaurant. Just kidding, she accepts his advances and his restaurant after he kisses her, catching her by surprise and totally turning her on. They date for a bit and everyone loves his riches but then they realize he's kind of insane. He wants to master the world from every angle and only has to do so physically at this point so he plans to become the world's ultimate fighting champion. He ends up in a full body cast and plans to try again. See ya, Pete.
Janice
Yup.
Bonnie
Bonnie was too good for Ross. You may remember her as the bald girl, and that's kind of all there is to say. She would have made more sense with Joey because she was so fun and carefree, I don't even know what she was doing with Ross in the first place. This girl was the type that could literally shave her head and still be a ball of sunshine the next day. Ross is not like that. At all. Ever.
Janice
Chandler's face perfectly represents how the rest of us feel about this.
Joshua
Joshua was boring. I mean, he was cute and nice enough but meh. Basically this relationship happened because Rachel was desperate and he has a good face. They go on about four dates and she proposes at the end. Yes. Proposes. He says, "No thanks, I'm good." Ouch. I would have said no, too. Sorry, Rach, but you were creepy with this one. And he wasn't worth your weirdo obsessing.
Kathy
CHANDLER. You messed this up every step along the way. First off, she was Joey's girlfriend and not meant for you. Secondly, once you got her, you're paranoia ruined it all. This thing totally could have gone all the way, man. They completely understood each other and had an undeniable connection, but she was an actress that had to hook up with someone on stage and Chandler's neurotic jealousy took over. I really did love Kathy, she had a back bone and got both Joey and Chandler. She also followed her heart, yet volunteered to take herself out of the equation once she saw what she did to the bromance. I'd say the only good thing that came out of this break up was Chandler being freed up for some sex with Monica in London, thus beginning my favorite Friends' love story.
Emily
No. Emily. No. There was no point during this relationship that I liked her or this relationship. Well, her voice didn't suck because everyone loves a British accent, but everything else was terrible. Ross always talked about how he did things when he was with Emily that he wouldn't normally do, but when that includes rugby and ear piercings, it's not quite as romantic as it sounds. I suppose her real crazy doesn't start until Ross royally screws up the wedding, so I'll give her that one. Who gets the name wrong at a wedding? Um, someone who shouldn't be getting married, Ross. They both rushed into the whole thing, and I really don't understand why. I can't figure out what connection they were holding on to because I was never aware of it but whatever. Luckily the whole thing went up in smoke before the honeymoon.
Danny
This was the rude Yeti-looking guy that had a disgustingly close relationship with his sister. I feel that covers the relationship.
Elizabeth
Despite the fact that she was one of his students, I actually didn't hate this relationship. It was weird, sure, but Ross is weird so that's bound to happen. Mostly it just felt temporary because you knew it couldn't last. They didn't have enough in common and seemed to mostly just have sex, which was fine, but again, temporary. She did force him out of his comfort zone from time to time which is always fun to watch because an uncomfortable Ross is the best kind. Plus this relationship let the others tease him mercilessly and that's always a good time. My favorite part of their relationship was Elizabeth's father because I mean... Bruce Willis.
Paul
And here is Bruce Willis. Aren't we all happy Ross was unethical and dated a student so we could get this guy on screen to date Rachel? All I remember about their relationship is that he wouldn't open up emotionally, so Rachel beat those walls down, and then he cried. And cried and cried. Forever. And it was bad and awkward but also hilarious and awesome because it was Bruce Willis and he was on Friends.
Janine
Janine was not worth Joey's time. She was rude and Australian and a dancer, so I see how a guy could go for her, but really she sucked. She had no personality but hated on Monica and Chandler, making Joey choose. He obviously chose his friends and good riddance, J... you are the worst and should never have come.
Tag
What a cutie. Tag was great but similar to Elizabeth in that you knew it wasn't a relationship that would last. He was too young and immature for Rachel, but it was quite a joy to watch because he was so adorable and fun. The episode where they meet and Rach hires him over a qualified middle-aged woman is amusing because that could never happen in real life. And the way she checked him out - you'd call up HR and have her reported, I mean, it was sexual harassment, but because this was TV, meh. I'll allow it. And they were an obnoxiously good looking couple, so there's that.
Eric
Sean Penn dressed up as a solar system. A SOLAR SYSTEM. He also dated Phoebe's twin sister who is a terrible person and he therefore couldn't date Phoebe herself because he was reminded of all the betrayal. Womp womp.
Mona
Mona, you are as forgetful to me as you were to Ross, and your biggest character flaw was dating him. He kept lying to you and clearly had feelings for Rachel; you were way too good for him. The fact that you stuck around so long was confusing to everyone, including your boyfriend because you are normal and put together and he is not. GET OUT, MONA.
Mike
Phoebe Buffay and Mike Hannigan, aka Princess Consuela Banana Hammock and Crap Bag, were perfect for each other. But really. I mean, let's talk about the way they met. Joey promised to set her up with a guy named Mike, but because he didn't know anyone with that name, he went into Central Perk and yelled "Mike." That's amazing. To make it better, once Phoebe figured it out, she was rightfully pissed, but let Mike prove he wasn't a liar and actually was a pianist, so he played the piano without an actual piano. She was completely impressed and there you go. But wait! He's divorced and doesn't want to marry again and she does. Neither willing to change their mind, they have to break up. NO. Mike. You're ruining everything. Phoebe deserves happiness and you're PERFECT for her. Fine. Whatever, David is back. That's right, the scientist. So Pheebs dates David and all is good-ish. I mean David is awesome, we all loved him but that's because we didn't know Mike yet. In true Monica fashion, she gets Mike to crash their group vacation and sorry not sorry, David, but you need to leave. So Mike and Phoebe are all happy and great and own rats together for a second. The best is that they try to propose to each other numerous times but it keeps not working out until finally it does. They have an adorable wedding in the middle of the street and all is perfect. These two are so cute it's annoying but so unbelievably flawless in all its quirkiness.
Charlie
Charlie dates Joey and Ross but there isn't a picture of her with Joey. Anyway, she's super smart and very cool. She makes no sense with Joey but perfect sense with Ross. Since she switches to Team Ross in season ten, it doesn't matter how great she is, we needed her to leave and make room for Rachel. So they write in her ex, who is still super in love with her, and they both make Ross crazy uncomfortable until he steps back. Charlie was also used to give Rachel and Joey the green light because if Ross can take Charlie, Joey can take Rachel. It's all very anti-feminist and not okay, but hey, everyone ends up where they are supposed to be.
Janice
HA. Janice is almost Chandler and Monica's neighbor, so they lie and tell her that Chandler isn't over her. It's great because this is Janice's reaction before leaving his life forever.
These people. At least everything worked out as it should.
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