The first episode of Friends aired in September 1994, which means that the beloved sitcom is now 30 years old. As it hits the best decade of its life — at least that’s what people say to all the millennials turning 30 — we’re forced to remember every Friends character’s love interest, from the worst to the best. While some short-lived ones were played by impressive guest stars such as Alec Baldwin, George Clooney, Brad Pitt, and more, others stuck around for multiple episode arcs.

While some love interests are hilarious additions to the 10-season show, others are there for us to despise. Whether they hurt our “friends” or they were just plain odd, the main six friends have dated some real characters. Between Phoebe’s terrible psychologist boyfriend to Monica and Rachel both going out with Jean-Claude Van Damm, there are more than enough Friends love interests to provide our official ranking.

14 — Paolo (Cosimo Fusco): Rachel, Seasons 1–2

Paolo is the obstacle to the iconic Ross and Rachel pairing. When Ross realizes he has feelings for Rachel, she meets Paolo in the blackout. And after he and Julie (Lauren Tom) break up because of his feelings for Rachel, she gets back together with him shortly. However, after he inappropriately hits on Phoebe by assaulting her during one of her massages, he officially makes the list as the worst Friends love interest.

13 — Janine Lecroix (Elle Macpherson): Joey, Season 6

Joey hits the jackpot when he gets his new roommate, a dancer named Janine, played by supermodel Elle Macpherson. However, when she hates Monica and Chandler for no reason, trying to make Joey choose her over his friends, it’s clear that she’s a villain.

12 —Kathy (Paget Brewster): Chandler and Joey, Season 4

Just before Chandler settles down with Monica, he falls for Joey’s girlfriend, Kathy. He meets her as she waits for a date with Joey, and although she’s a likable enough character, she cheats on both Joey and Chandler. “Once a cheater, always a cheater,” isn’t always true, but the foreshadowing for Kathy was strong. We all wanted Chandler to just be happy, but instead, she made his worst nightmare come true, so she falls pretty low on the ranking of love interests.

11 — Richard Burke (Tom Selleck): Monica, Seasons 2-3

Many Friends fans tend to rank Richard higher on the list because he was a good boyfriend and partner to Monica. However, he was 21 years older than her! He knew her when she was a child and he’s a friend of her dad’s. Their relationship is beyond inappropriate, even if she is a consenting adult. Not only did they have an age gap in which Richard held a bit more power, but he always knew he didn’t want to have kids again, while Monica always wanted to be a mother. Just don’t date if that’s the case! The hurt that Monica felt when they broke up lasted several episodes, so he should have known to not even entertain it to begin with.

10 — Emily (Helen Baxendale): Ross, Seasons 4-5

Ross and Emily’s wedding is infamous, and for an apt reason. Ross accidentally says, “I take thee, Rachel,” when marrying Emily, and she’s (understandably) furious. But from the moment she shows up, she’s contrary and stubborn. So when Ross messes up, she leans into that side of her personality to try to control his every movement, and even tries to stop him from seeing Rachel. While he agrees at first, he realizes that’s not the basis for a solid marriage and thankfully breaks things off, but not before we can a likable love interest become the villain.

9 — Charlie Wheeler (Aisha Tyler): Joey and Ross, Seasons 9-10

Charlie starts out as a hilarious attempt at diversity casting from the Friends production team. However, when she and Ross seemingly connect on an intellectual level, she ends up making out with Joey instead. But the shot to Ross’s heart isn’t enough — she has to spend weeks dating Joey before she realizes she has feelings for Ross. Then, when she does date Ross (who’s going through his own reckoning while Joey dates Rachel), she realizes she still has feelings for her ex-boyfriend, Benjamin Hobart (Greg Kinnear). Get it together and figure out your feelings before breaking hearts, Charlie!

8 — Pete Becker (Jon Favreau): Monica, Season 3

A fun departure from Monica’s typical careless ex-love interests, Pete goes after her like there’s no tomorrow. At times, his determination to win over Monica is creepy (he writes her a check for $20,000), but in the end, it’s an admirable effort when she falls for him. However, they break up for the weirdest reason of any love interest: he decides he wants to be the world’s best MMA fighter because he needs to conquer every area of success. Talk about an ego! Monica needs someone who can appreciate her success as much as their own.

7 — Elizabeth Stevens (Alexandra Holden): Ross, Season 6

Like the Richard-Monica relationship, Elizabeth and Ross had a major age gap. Not only that, but he was her professor! However, Elizabeth isn’t the villain here, as Ross was in the power position to be able to say no. Her dad (rightfully) disapproved of their relationship, and ultimately, their maturity levels just didn’t match. She wasn’t a bad person at all, but dating Ross was definitely not good for either of them.

6 — “Fun” Bobby (Vincent Ventresca): Monica, Seasons 1-2

“Fun” Bobby wasn’t in too many episodes and never seemed like a serious love interest for Monica, but their relationship was always fun. He knew how to joke around and every “friend” loved him … until they realized that he was only “fun” because he was an alcoholic. Even still, this doesn’t make him a bad person. In fact, he quit drinking just to keep his relationship with Monica. The storyline was a strange one, with the writers deciding to make him boring after he stops drinking, but he’s also a reminder to not rely on alcohol in social situations.

5 — Susie Moss (Julia Roberts): Chandler, Season 2

Some might say Susie is a pretty bad ex considering the fact she embarrassed Chandler to the nth degree. However, he deserved it! We love a woman who puts one of the “friends” in their place, and Chandler caused Susie’s unfortunate “underpants” nickname throughout her school years. The fact that Julia Roberts decided to be in a Friends episode and she gave Chandler what he deserved? We stan Susie Moss.

4 — Tag Jones (Eddie Cahill): Rachel, Season 7

When Rachel turns 30, she’s dating the lovable Tag, portrayed by Miracle actor Eddie Cahill. He’s handsome, young, and fun, which is everything we want to be. However, Rachel realizes she’s getting to the age when she wants to settle down and start a family, but Tag is just not there yet. That doesn’t make him or Rachel a bad person — their connection was just made at a bad time. And while we don’t condone dating an employee, their flipped power and gender dynamics made a fun relationship to watch in the later seasons of the show.

3 — David the Scientist Guy (Hank Azaria): Phoebe, Seasons 1-10

Phoebe was actually supposed to end up with David the Science Guy, but viewers loved her soon-to-be husband, Mike, so much, that the writers had to abandon the series-long romance with David. He popped in and out after they met. He was called to Minsk for a once-in-a-lifetime career opportunity, but in choosing that, he lost out on Phoebe. For a while, we thought they were end goals, but Phoebe had to end up with someone who matched her high quirky energy, whereas David was a little too pensive and hesitant in the end.

2 — Janice Litman-Goralnik (Maggie Wheeler): Chandler, Seasons 1-10

Shout it from the rooftops — Janice is a feminist icon. She has zero cares about what other people think. She’s authentically herself with the high-pitched voice and nasally laugh and yet, there’s something so endearing and charming about her. Now, we are forgetting about when she cheats on Chandler with her ex-husband and breaks his heart — obviously, that sucks. But we love her and what she represents. Sometimes people mess up, and that’s what happened to Janice. But luckily, her mistake means that Chandler falls in love with Monica in the end!

1 — Mike Hannigan (Paul Rudd): Phoebe, Seasons 9-10

Everybody thought that Phoebe would end up with David the Scientist Guy, but when Mike shows up, everyone falls in love with him. He fits in perfectly with the six friends and comes in with a big personality of his own, full of sarcasm and musical talent. He loves and supports Phoebe for who she is, even after she cries all throughout their date, and despite his very human missteps of not wanting marriage after a bad experience, he ultimately decides to marry Phoebe. Who could be better? No one.