Love is difficult. So are romantic relationships and dating. Choosing the right person, The Simpsons prove this as well.
Fans might think the show doesn't put that much emphasis on romance, but throughout its long existence, it actually created a lot of notable couples. Some of them lasted a long time (Homer and Marge, of course), while others weren't so lucky. Unfortunately, when the romance failed or didn't even properly begin, it was because of the characters' bad choices so they're the ones to blame.
Lisa Gives Ralph A Gift
This couple proves sometimes even the best intentions can cause troubles. Lisa gives a gift to Ralph when nobody else gives him any just because she feels sorry for him. As a result, Ralph thinks Lisa likes him and he keeps asking her out.
Lisa tolerates it because she doesn't want to hurt his feelings but she eventually snaps and breaks his heart. Lisa meant well, of course, but if she was honest from the beginning, none of this would have happened.
Apu Cheats On His Wife
Apu and Manjula struggled with the idea of an arranged marriage, but they made it work nonetheless. That doesn't mean their marriage was perfect; Apu made one of the worst choices when he decided to cheat on Manjula with Annette, the Squishee Lady.
Annette is funny and beautiful, of course, but instead of trying to solve his marital problems, Apu takes the easy way out. Manjula forgave Apu in the end but not before seriously considering divorcing her unfaithful husband.
Artie Keeps Pursuing Marge
The Simpsons presented some serious issues in a funny way. When one thinks about it, it's not such a stretch to call Artie Ziff a stalker. Artie was Marge's prom date but she chose Homer in the end.
Instead of respecting it, Artie kept pursuing Marge and wanted to get her for himself. He simply couldn't take the hint. He even went as far as to spy on Marge and Homer in the comfort of their home. If this isn't the creepy work of a villain, it's hard to say what is.
Selma Gets Together With Sideshow Bob
Marge's older sister Selma hasn't had the best of luck at relationships. One of her worst choice for a romantic partner was the villainous Sideshow Bob. Selma knew Bob had a criminal record and held a grudge against the Simpson family.
Yet she chose to marry him anyway even though Bart warned her. And it turned out Bart was right; Sideshow Bob tried to kill Selma, and if it wasn't for Bart, he might have succeeded.
Lisa Dates Nelson Muntz
This strange couple fulfills the old trope of the good girl who falls for the bad guy. It rarely works in real life, and it also didn't end well on the show.
The romance was weird from the start; Lisa wanted to change Nelson into someone else and he didn't even originally like her that much. The first time he kissed her, Nelson did it not because he liked Lisa but because he wanted to stop her from talking. In the end, they worked better as friends.
Lisa's Jealousy Gets The Better Of Her
Lisa is the ultimate proof even the smartest person can make a silly mistake when it comes to love. Lisa falls for Luke when they meet during the episode "Dude Where's My Ranch." For a while, it looks like they might be happy together but Lisa ruins it when she puts Luke's sister Clara in danger.
The reason why Lisa did this was she thought Clara was Luke's secret girlfriend and she decided to deal with it this way instead of just asking Luke about Clara. If she talked to him about it, she could have saved herself the subsequent heartbreak.
Lisa Falls For A Boy Who's Like Her Dad
Lisa is a smart girl, and ideally, she would find a partner who complements her. This wasn't the case with Lucas whose only ambition was to be a competitive eater.
Considering his love for food, Lucas (or rather, Luca$) was very similar to Homer in some aspects. There's not necessarily something wrong with it but Lisa and Lucas' personalities are very clearly mismatched, and ultimately, Lucas dragged Lisa down. Thankfully for all those involved, the relationship ended quite soon.
Lisa's Future Selection
The show has multiple episodes which played with the idea of what the family's future could look like. In one of the episodes called "Lisa's Wedding," the adult Lisa dated the British student Hugh Parkfield. Lisa and Hugh argued when they first met which should have been a red flag.
Lisa dated Hugh anyway, and he asked her to marry him. But Hugh then insulted Lisa's family and said because of their inappropriate behavior, they would never see them again. Lisa was naturally disappointed by this and called off the engagement.
The Bad Boy Falls For The Even Worse Girl
Jessica Lovejoy (played by guest Meryl Streep) posed like a sweet girl but in reality, she took advantage of Bart. Even when Bart realized what Jessica was doing, what was she really like, he kept coming back to her. It was a mistake that later blew up on him since Jessica made it look like Bart was responsible for all the bad things she'd done. Luckily for Bart, the truth came out in the end and Jessica was rightfully exposed.
Smithers Loves Mr. Burns
It's obvious Mr. Burns' assistant Waylon Smithers loves his boss. But the issue with this decision is Mr. Burns doesn't deserve such affection in the slightest; he treats other people, Smithers included, horribly. Mr. Burns does have his better moments, but overall, he's a terrible person and doesn't deserve such deep affection from Smithers.