Ever since he was introduced on Friends, Joey Tribbiani has been known as something of a ladies’ man. He’s had tons of one night stands and casual relationships, but when you dig into his time on the series, he hasn’t had that many serious relationships.

The ones he did have run the gamut from the “really, really great” to “what were they thinking?” Given the plethora of interesting women Joey has dated over the years, we decided to rank the five best, and the five worst relationships Joey Tribbiani has had on Friends and Joey.

BEST: KATIE

In season five, Joey started dating a girl named Katie, and she seemed like the perfect girl for him. She was sweet and fun, and energetic… the whole gang really liked her. Unfortunately, there was something she did that made her unappealing to Joey forcing him to eventually break things off with her..

She had this annoying habit of punching him whenever she wanted to make a point or laugh at his jokes. It was irritating, and it led to his breaking up with her, which is a shame. They were really great together… when she wasn’t punching tiny bruises into his arm…

BEST: JANINE

Janine moved into the apartment with Joey in season six after Chandler moved out, and since she was played by supermodel Elle MacPherson, Joey was immediately infatuated with her. The only problem was, she wasn’t into him, and none of his usual charms worked on her… at first.

Joey’s perseverance paid off, and the two began to date. He really liked her, and things were looking as if he had found “the one” until they had some couples time with Monica and Chandler. Janine absolutely hated them both, and when it came to choosing Janine or his friends, Joey chose the latter.

BEST: KATHY

Kathy was an amazing girlfriend to Joey when they first started dating. She was perfect in every way, and while Joey clearly enjoyed spending time with her, there was a problem with their relationship in the form of Joey’s roommate. Chandler had a much better connection with Kathy than Joey did, which presented a problem.

Even though the two were great together, Chandler eventually got in the way. Kathy was into Chandler as much as he was into her, and eventually, she split up with Joey to date his roommate. That relationship didn’t last long, which proved she was probably better off with Joey the whole time.

BEST: ERIN

Joey slept with Erin on their first date… which isn’t something that’s particularly unusual for him, but things didn’t proceed in their normal fashion from that point. When she got up the next morning, Rachel was supposed to show her the door, but the two women bonded and became friends.

When she and Phoebe pushed Joey to continue seeing her, he ended up falling for Erin pretty hard. It all seemed to be going perfectly well until Erin “pulled a Joey” and wanted to call the whole thing quits. It ended up hitting Joey pretty hard, and the audience was left wondering, “what if…”

BEST: ALEX

Alex wasn’t a character on Friends, but did play a major role on the spinoff series, Joey. She played his neighbor, and Joey was immediately attracted to her. For the majority of the series (it only lasted for two seasons), the couple played a “will they or won’t they” game of back and forth.

Eventually, they gave in to their desires and the two started dating in the closing episodes of the second season. It looked as if they might make it work as the series came to the close, and Joey even described her as “the first girl he had ever thought about being married to.”

WORST: CHARLIE

Charlie was gorgeous and amazing, and completely wrong for Joey. The two were a great couple from the outside looking in, but when you dig a little deeper, they had no business trying to make a real relationship work. Charlie was ridiculously intelligent and worked in Ross’ field, which made her an ideal woman for him.

Eventually, Joey went to a new relationship while Charlie finally realized Ross the right guy for her. Things were looking good when Joey and Charlie’s relationship came to an end, but ultimately, she didn’t end up with anyone in the gang as she went back to her ex-husband instead of staying with Ross.

WORST: KATE

When they first met and began to work together, Joey was completely infatuated with Kate. He tried everything to get her to go out with him, but she showed no interest whatsoever. As they worked more and more on the play, she found that she was attracted to him and they began a relationship of casual sex

Joey was way more into Kate than she was into him, which is why she ended up leaving him (without saying goodbye). He found out about it during a live performance of the play, and it clearly broke Joey’s heart as he said goodbye via his lines in the play.

WORST: ERIKA

Erika was a beautiful woman who was completely and totally in love with… Doctor Drake Remoray. Let’s just say, she had some issues, but seeing as she was played by the beautiful and amazing Brooke Shields, Joey had a hard time saying no to her advances… and it’s hard to blame him for that.

The two started messing around, but Joey recognized she was a little crazy. She couldn’t understand that Joey wasn’t literally the character he portrayed on screen, so there wasn’t any way a relationship would have actually worked between the two. He was able to break things off using some soap opera logic, and she went on her way back to crazy town.

WORST: URSULA

Ursula is Phoebe’s twin sister, and when she was first introduced on Friends, Joey was all over her. He immediately went after a relationship with her, which Phoebe absolutely hated. She knew her sister was incapable of showing Joey the love and affection he deserved, and in the end, she was proven right.

Phoebe ghosted Joey, which tore him apart. In the end, Phoebe pretended to be her sister so that she could break things off with him for her. It worked, but after she kissed him, Joey realized it was his friend all along, which made for a sweet moment in their friendship.

WORST: RACHEL

When Joey and Rachel became a thing on Friends, pretty much everyone hated it. The fans didn’t know what was going on, and the entire cast hated the idea, but it ended up making it to print regardless. Joey initially had an infatuation for Rachel that went away, but when they went to Barbados, they started fooling around.

That helped to end Joey’s relationship with Charlie (and send her to Ross), but the two were never able to consummate their relationship. Every time they tried, Rachel slapped Joey because… he was Joey. They decided to remain friends and put their physical desires to rest, which was a relief to everyone.