Every Penny And Leonard Engagement Scene In The Big Bang Theory, Ranked

When Leonard Hofstadter, one of the main nerds on "The Big Bang Theory" portrayed by Johnny Galecki, first lays eyes on his new neighbor Penny (played by Kaley Cuoco), he's immediately smitten; he even tells his best friend and roommate Sheldon Cooper (Jim Parsons) that the babies he wants to have with her will be "smart and beautiful." Honestly, Penny is lucky that Leonard didn't propose marriage a few minutes into their first meeting, but eventually, he does start asking her to marry him — but luckily, they're actually dating by the time he gets around to full-fledged proposals of marriage. (Penny also initiates one of them, but hang tight; we'll get there.)

All in all, a marriage proposal (in some form) comes up a whopping five times between Leonard and Penny throughout "The Big Bang Theory," and incredibly, only one of those times results in an actual engagement. (They also get married twice, partly because their first wedding is such a dud and resulted in one of the show's all-time worst episodes, but that's another matter entirely.) I've gone ahead and ranked all of the "engagement scenes" — or, as most of them are, marital near-misses — for you from worst to best, because to be absolutely frank with you, a lot of them are misguided attempts to fast-forward Leonard and Penny's relationship, with a lot of the "blame" for that resting on the former. (Come on, Leonard. Chill out.)

Proposing while you're drunk is never a good idea, and proposing while you're drunk and experiencing a bitter professional disappointment is an even worse one. This is why Penny's hasty and even desperate proposal to Leonard in the Season 7 episode "The Hesitation Ramification" is easily the worst attempt at nuptials in the pair's relationship. At the beginning of the episode, Penny is thrilled to tell Leonard, Sheldon, and her friends Amy Farrah Fowler (Mayim Bialik), Raj Koothrappali (Kunal Nayyar), and Howard Wolowitz (Simon Helberg) that she booked a guest role on "NCIS" alongside star Mark Harmon ... but when they all sit down to watch the episode together, Penny is absolutely devastated to learn that all of her footage landed on the cutting room floor.

Penny falls headfirst into a bottle of wine and goes to Leonard and Sheldon's apartment, telling Leonard that, aside from their relationship, she has absolutely no idea what she's doing in life (and includes the utterly charming detail that, while waiting in line at Starbucks, a pair of dirty underwear fell out of her pant legs and weren't even the only pair she found in there). In a moment of obvious desperation, Penny gets down on one knee and proposes to Leonard, who says no because she's obviously intoxicated and just generally freaking out. The episode ends with Leonard and Penny fully on the outs — after Leonard says "uh" in response to her proposal, Penny flees and insists she needs to be alone — so really, the entire installment is pretty bleak where this couple is concerned.

It's Valentine's Day in Pasadena during the Season 6 episode "The Tangible Proof Affection," and literally nobody is happy. (Frankly, that's what you get for putting a ton of pressure on a random day in February to be perfect and romantic, but I'm a cynic.) While Raj organizes a night for single folks with comic book store owner Stuart Bloom (Kevin Sussman, aka the man who was almost Howard Wolowitz), Leonard decides to take Penny out to a fancy, romantic restaurant, and after Howard accidentally ruins his gift to his wife Bernadette (Melissa Rauch), having gotten her a grain of sand inscribed with their initials that took him 12 hours to make, Bernadette and Howard ultimately join them for a double date.

Bernadette and Howard are already fighting by the time they arrive at the restaurant — Howard didn't do any chores, so Bernadette hid his Xbox — and in the middle of their argument, Penny sees her ex-boyfriend dining with his own date at the restaurant ... an ex-boyfriend who cheated on her with her friend, who happens to be the date in question. When Penny's ex proposes to his paramour, Leonard barely gets his own proposal out before Penny tells him to shove it, and they end up fighting when they get home. (This makes Bernadette and Howard feel better about their own problems, naturally.) Penny and Leonard keep duking it out when they get home until Leonard then declares that Penny has to be the one to propose to him and demands that Penny sweep him off his feet, so it's definitely unfortunate that this announcement is followed, one season later, by "The Hesitation Ramification." 

Also, Leonard calls Penny a "b****" in this episode, so that's not great. (She calls herself one first, but still.)

Everything's going pretty well between Penny and Leonard in the Season 5 episode "The Launch Acceleration" until partway through the episode — when, after taking things slow for a while, they hop into bed together and Leonard, apparently, proposes during sex. (This is a sitcom, so obviously, we do not see this happen.) What we do see is them running out of the room, with Penny in an oversized tee and Leonard in her frilly pink robe, and Penny is seriously upset; as she points out, a marriage proposal during an intimate physical moment isn't exactly standard. (When Leonard asks if they can go back into her bedroom and give it another shot, Penny quips that his next query will be, "Hey baby. Want to go look for houses in neighborhoods with good schools?")

This haunts their relationship for a good portion of the episode until Leonard catches Penny in the hallway when she's heading to her job at the Cheesecake Factory. Penny kisses Leonard and officially turns down his impromptu proposal, though he does follow her down the hallway to ask if they're still dating. She says they are, but she's very clearly irritated with him, so it's not exactly a good indication of future proposals to come.

At the end of Season 7 of "The Big Bang Theory," the gang learns that Arthur Jeffries, the TV star known as "Professor Proton" (played by real-life comedy legend Bob Newhart), recently passed away ... and Penny and Leonard are the only ones who go to his memorial service. Leonard, thinking about his regrets at the funeral, says he regrets saying no to Penny's drunk proposal in "The Hesitation Ramification;" she immediately tells him not to do it right then and there noting that he has a "propose face." In response, Leonard says that he's "losing" a sort of twisted proposal contest because he's proposed twice and she's only done it once, so Penny "proposes" again and tells Leonard he needs to propose to her. Naturally, Leonard really makes a meal out of this, saying he doesn't want to have any regrets while Penny, slightly and understandably horrified at the idea that they'd get engaged at an old man's funeral, tells him to say no so they're "even."

This doesn't end at the funeral. During their car ride home, Penny insists that Leonard say no and says "Will you marry me, yes or no," which Leonard twists into another proposal ... making Penny mad. Finally, Leonard says no, though he still clings to the whole "second proposal" bit. It's a little exasperating to watch Leonard rub this whole thing in Penny's face, but here's the flip side: the fact that they're joking about it and both seem like they do want to eventually get married is a more encouraging sign than we've seen up until this point.

True to form, even Penny and Leonard's actual proposal — the one that ends with them legitimately getting engaged — is awkward. Immediately following "The Proton Transmogrification," the penultimate episode of Season 7 of "The Big Bang Theory," titled "The Gorilla Dissolution," focuses largely on Penny's flagging career as an actor as she heads to set to shoot the clearly terrible "Serial Ape-ist 2" alongside Wil Wheaton (who, as he does many times throughout the series, plays himself). Leonard tags along to be supportive before realizing that the movie's director doesn't care, and when Penny asks the director to re-shoot a scene, they get into a fight and she gets fired; when Wheaton stands up for her, he gets fired too, and all three leave the set in disgrace.

Back at Penny's apartment, she says she needs to start making better choices with her life, at which point she suggests that they get married. Leonard, not taking her seriously, says she only wants to marry him because he's a "smart decision" like a "bran muffin," spiraling about being the "boring" choice simply because he's good for her. The two start fighting — yes, again — until Penny says that getting fired from "Serial Ape-ist 2" was the best thing that ever happened to her because she realized she only needs one thing: "you, you stupid Pop-Tart!" They realize this is the real deal and, for the very first time, Leonard produces a ring that he says he bought a while ago after they agree that all of this was a bit anti-climactic; the two kiss, finally engaged for real this time.

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