The Simpsons: The 5 Best & 5 Worst Relationships

Marge Homer Simpson

The Simpsons remains one of the most beloved and longest-running television shows of all-time. It's hard to say what has made it such a success for so many years, but its willingness to lean into outrageous humor is certainly one of its strongest qualities. Even though the show is known mostly for its comedic gags, The Simpsons occasionally makes some time for romance as well.

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With an endless list of established characters in the town of Springfield, there are been some truly memorable romantic pairings over the years. Some of these love stories have proven to last the test of time. Some have ended far too soon. And then there are some that were destined for disaster. Here are the best and worst relationships from The Simpsons.

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10 Best: Skinner & Edna

In a romance that united two of Bart Simpson's sworn enemies, Seymour Skinner and Edna Krabappel proved to be a pretty solid pairing. The two had butted heads as teacher and principal in the past, but they soon find a mutual attraction which helps end their respective loneliness.

Though both Skinner and Edna have had other high-profile romances on the show, this is the one that seemed to make the most sense for both of them. Skinner's dry and proper behavior suited Edna's cynical nature wonderfully. It was Skinner's overbearing mother that led to their break-up, and since Edna was killed off in the show, there's sadly no chance for a rekindling of this romance.

9 Worst: Comic Book Guy & Agnes Skinner

Everyone needs love in their life, but it's hard not to get grossed out by this May-December romance. Comic Book Guy and Agnes Skinner are two of the most unpleasant characters on the show. He is a sarcastic and belittling slob, while she is a demanding and critical old woman. Somehow these two found each other, much to the disgust of everyone around them.

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It's hard to say which of the two is more unattractive, but seeing them together is enough to make your stomach turn. Thankfully, the nauseating romance didn't last long, but not before we had to see the terrifying image of them in bed together. We will never forgive the show for that.

8 Best: Grandpa Simpson & Bea Simmons

Abe Simpson is not the easiest man to love. He has always been a rather rude and prickly man, even before his seniority kicked in. But he has seemed to soften over time, and in many cases, he has looked for love to bring some happiness into his life. One of the most promising, and ultimately sad, relationships he was in was with Bea Simmons.

The two met at the Springfield Retirement Castle with a meet-cute when their medications got mixed up. It proves to be love at first sight. With Bea, Abe seemed happier and livelier than he ever had before. Sadly, when out with the Simpsons family, Bea passed away, leaving Grandpa Simpson alone again.

7 Worst: Selma & Sideshow Bob

Selma Bouvier, one-half of Marge's twin sisters, may have had the most relationships of anyone on the show. Despite living her entire life with her twin sister, Patty, Selma is very lonely and has incredibly low standards for the men she dates, including Disco Stu, Lionel Hutz, and Abe Simpson.

However, her worst decision had to have been Sideshow Bob. Dating a criminal mastermind who tried to kill your nephew seems like an obviously bad decision. But Selma falls for Bob due to his charming personality. His one downside is revealed to be that he planned to kill Selma for the insurance money, which is a pretty clear deal-breaker.

6 Best: Bart & Laura Powers

Bart might play it cool, but deep down, he wants love just as much as anyone else. One of the earliest romances we see Bart involved in is with his new next-door neighbor, Laura. Moving in with her single mother, Laura proves to be remarkably similar to Bart in terms of humor and mischief.

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Unfortunately for Bart, Laura is several years older than him and has a relationship with Jimbo Jones, one of Bart's frequent bullies. Despite it being an unrequited love, Bart shows a new side of himself with his infatuation, and we haven't really seen him as taken with a girl since then.

5 Worst: Bart & Jessica Lovejoy

Normally Bart Simpson would be the last person parents would want to date their daughter. When it came to his short-lived relationship with Jessica Lovejoy, he was actually the less-destructive one.

Jessica was the seemingly angelic daughter of Reverend Lovejoy, who only took an interest in Bart when he proved to be a genuine troublemaker. She pushed the limits of what even Bart was willing to do, showing herself to be the ultimate bad girl. In the end, she let Bart take the blame for her own crimes. It takes a pretty devilish child to make Bart look good.

4 Best: Lisa & Nelson

Lisa is often more preoccupied with her many intellectual pursuits. However, she does occasionally fall head over heels for a boy. No one could have predicted Nelson Muntz would be one of those suitors. Few characters on the show seem as different as Lisa and Nelson. His rebellious nature was very much at odds with her straight-laced personality. Despite all this, they managed to be pretty good for each other.

They end up showing each other a new side of themselves, and for Lisa's first romance, she learns quite a lot. Both Lisa and Nelson are surprised by the romance and even more surprised by how much they like each other. But in the end, their very different paths separated them.

3 Worst: Lisa & Ralph

While Lisa found herself unexpectedly drawn to Nelson Muntz, when it comes to Ralph Wiggum, she was much less enthused by the romantic relationship. Pity is probably not the best place to begin a relationship, but when Lisa felt sorry for Ralph for not getting any Valentine's Day cards, he took her kind gesture to mean they were in love.

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The relationship was always doomed to fail because Lisa, sadly, did not have any interest in him beyond a casual friendship. Soon Lisa finds herself stuck in this unwanted romance which leads to her breaking Ralph's heart in a very public way.

2 Best: Marge & Homer

Marge Homer Simpson

It makes sense that the relationship at the center of the show should also be the show's best relationship. Starting as high school sweethearts, Homer and Marge's love for each other has stayed as strong as ever, which led to them building their dysfunctional yet loving family.

Clearly, Homer and Marge's relationship is by no means perfect. The show has depicted many rough patches in their relationship and showed they both have their faults—though Homer probably has a few more than Marge. But they always seem to overcome their problems and continue to make it work. It helps that they are absolutely in love with each other.

1 Worst: Marge & Artie Ziff

In some alternate Simpsons reality, the show would be called "The Ziffs" and would be a lot less lovable. Artie Ziff is the man who nearly came between Homer and Marge early in their relationship. When Homer and Marge briefly broke up, Artie swooped in as her prom date. However, his aggressive and perverted nature ended the date abruptly with Marge rekindling things with Homer.

Since high school, Artie became a successful businessman, but he has never gotten over Marge, obsessing over her constantly. He has tried several times to take Marge from Homer and remains persistent despite always failing.

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