There's a long-running gag on The Big Bang Theory that Penny has been with her fair share of men. Before dating Leonard (and even in between breakups), Penny has been seen with various guys without so much as an explanation of the meaning of their relationship. She's a beautiful woman who has it easy when it comes to dating.
However, after dating Leonard (and hanging out with Sheldon, Howard, and Raj), Penny's male preferences change as years go by. She's no longer interested in the muscle head type and prefers being mentally stimulated. It's around this time that Penny realizes just how much she loves Leonard and that he was the one for her all along. But it took kissing a few frogs to get to that point. From one-night stands to short-term lovers, let's rank all the men Penny has been with from worst to best.
Mike (Season 1, Episode 14)
In case you don't Mike, he's the one who insists on giving Penny a hand in changing before their date when she was talking to the guys. This is the same episode where Leonard and co. bought a life-size time machine that takes up the entire living room.
Penny was late to work due to the guys trying to move the machine, and it prompted her to insult them for liking such childish things. Meanwhile, her relationship with Mike was going nowhere fast because he's the one who blogged about their bedroom affairs and was already with another woman the second they broke up. It appears anyone was better for Penny than Mike.
Doug (Season 1, Episode 3)
There are a few men on this list that don't ring a bell for Big Bang Theory fans, but that's the beauty of Penny. In the early seasons, she dated around because she was new to the area and totally unattached.
In "The Fuzzy Boots Corollary," Penny is seen kissing Doug at her doorstep when Leonard tries to interrupt them because he has her mail. Doug's only words were "What's up, bro?" but it was enough to make Leonard compare the differences between them. Funny enough, it was after meeting Doug that Leonard had the courage to ask Penny out to dinner.
Eric (Season 2, Episode 2)
We meet Eric in the second season when the two are on their way to a date. Leonard, Sheldon, Raj, and Howard are just getting home from a Renaissance fair and are very embarrassed to be dressed in such a way in front of Penny's hunky new man. It's even more embarrassing for Leonard because Eric is the first man Penny's dated since going out with Leonard at the end of Season 1. But by the end of "The Codpiece Topology," Penny is seen making out with Eric while Leonard makes out Leslie. The two see each other kissing other people and seem to be in a strange kissing competition. But by the end of the night, that was the last we saw Eric.
Raj
To be fair, Raj is the only man on this list that Penny didn't actually date; however, the two have had more romantic moments than most friends do. Penny was Raj's date for his People Magazine 30 Under 30 award.
After a few drinks, Raj even introduced her to his parents as his "new squeeze." While they were just friends at this point, the two did eventually hook up, which caused a huge rift in the friend group. Even when Penny married Leonard, and Raj moved in with them for a short time, the two got along swimmingly. But as we know, Penny and Raj two were always meant to be friends — and just friends.
David
David and Penny could have been something magical if he didn't turn out to be married. He was tall, buff, and extremely smart — things Penny was looking for in a man by the second season.
David was a well-known physicist who came to Caltech to work with Leonard. Leonard was a huge fan of David's, and was excited to work with him, but that excitement died down when he introduced him to Penny. Penny was taken aback by David's wit and charm, and ended up going out to eat with him shortly after meeting. The two begin seeing each other and he even gave her a tour of the university, which confused Leonard. Sadly for Penny, their relationship crashed and burned when she found out he was married. Although David used Penny as his mistress, these two could have been the perfect match if he was single.
Kurt
Kurt seemed like a horrible person, but there had to have been a reason that he and Penny dated for four years. They must have shared something special for a strong woman like Penny to hang around for that long. However, Kurt did not have a good reputation with Leonard, Sheldon, Howard, and Raj. He was condescending and rude and bullied the guys when they approached him for Penny's TV and the money he owed her. He also bullied Leonard at Penny's Halloween party.
All in all, Kurt was an awful human being, but he's made it this far on the list because he dated Penny for four long years, proving their relationship had to have been special at one point.
Stuart
That's right, Stuart beat out Kurt, Raj, and all of the boys Penny has loved before. Before Stuart became more known in the series as an introvert who's terrified of women, he was brave and bold with Penny upon first meeting her.
They met during Penny's first trip to the comic book store and Stuart (somehow) impressed her enough to go on a date with him. They actually went out a few times. Penny seemed to really like Stuart but ended up calling him "Leonard" after too many glasses of wine, proving that she still had feelings for Leonard.
Zack
Oh, sweet Zack. Similar to Penny and Leonard, Penny and Zack also had a great friendship that kept their romantic relationship strong. We first met him in the third season and believe it or not, he got along great with Leonard and co. (even though the guys made fun of Zack for being kind of an air-head). Penny and Zack even got married in Vegas. The two didn't seem to have a lot in common, but Zack was loving and faithful to Penny — something many of her past boyfriends weren't. Heck, the two even remained friends after they broke up. Zack wasn't the smartest but he sure was the nicest.
Leonard
We can't have a list of Penny's best and worst lovers and not have Leonard as Penny's best prospect. He opened her eyes and made her see the world in a new way, and she gave Leonard the loving security he was always looking for. They may seem like complete opposites but these two totally rely on and trust one another — more so than any of their respective relationships on the show. Penny and Leonard were always meant to end up together.
