The Simpsons have had a lot of stories over the decades. And with so many
seasons under your belt, you’re gonna tread over common ground more than once.
One plot the Simpsons likes to dive into, happening as early as Season 4
and maybe earlier, is giving love interests to the Simpsons children.
Bart and Lisa have had multiple love interests and romantic relationships over the years.
These relationships range from amazing and healthy down to toxic waste levels of awful.
And today, we’ll be discussing Bart’s relationships.
I’m Brad with WickedBinge and this is Bart Simpson Romantic Relationships: Healthy to Toxic.
As we start our list, we start with the best of the best and move down, these are The Healthy
Starting off our list and earning our Gold Medal of Healthiness are Bart and Mary Spuckler.
Mary is Bart’s major love interest, appearing in three major roles and a multitude of cameos.
She and Bart first meet in Season Nineteen’s “Apocalypse Cow” where she helps Bart in caring
for his cow Lou, and to save Lou from a slaughterhouse, Bart takes Lou to Mary.
This leads to Bart being forced to marry her due to the “law of the hill-folk”,
although they call off the wedding. However, Bart and Mary are quite good together,
as they share some interests and are obviously interested in each other to some degree. However,
in her most recent major appearance, Bart and Mary really start dating but Bart starts to
ignore her and neglect her. However, it’s because he’s a ten-year-old boy,
it’s to be expected from him. However, Bart does really care about Mary and even tries to get back
together with her at the end of the episode, but we never see where this leads. Sure, Bart is not
the best in relationships, but these two are the closest it gets to perfect in Bart’s repertoire.
Taking our Silver Medal of Healthiness is Bart and Laura Powers. Laura is Bart’s earliest romantic
interest, appearing in Season Four’s “New Kid on the Block” where she was babysitting Bart and
Lisa. Now Laura is a bit older than Bart and this is really a one-sided crush for the most part.
Laura is attracted to bad boys like Jimbo and this does make Bart feel like his heart was destroyed
when he found out. Yes, Bart does cause Moe to come over in a rage and nearly kill Jimbo, but
we’re not accounting for that just right now. The thing is, Laura does say that if Bart were older
maybe they would date, which shows that despite what may be a bit of attraction on her part,
she has the standard not to date a ten-year-old.
They rank this high because they don’t have a lot of stuff to go over,
but Laura is a good person and a much better “older girl” for Bart, as we’ll see later.
Up next on our list and grabbing the bronze medal of Healthiness are Bart and Sherri/Terri. Now
we say Sherri slash Terri because it’s unclear which of the two he is most often romantically
involved with. In Season 12’s “Hungry, Hungry Homer” he goes to a dance with one of them,
and the two are mentioned to have been together by Homer at one point. Even in the admittedly
non-canon “Barthood” he is seen making out with one of them. The problem is,
that even though this relationship is mentioned repeatedly, including one of
the twins having a crush on Bart, they’re not really fully together. So we have to give them
bronze because there’s nothing toxic about these relationships but they’re not full ones either.
Rounding out the good section of our list are Bart and Gina Vendetti. Bart and Gina get together in
Season 15’s “The Wandering Juvie” when the two of them are both in juvenile detention.
The two are essentially forced together because of a juvie dance that is supposed to introduce
the boys to the girls. They both escape juvie and Bart, being a ten-year-old doesn’t understand her
few advances. Bart and her split up after a kiss and their handcuffs are broken, and it’s
revealed that Gina doesn’t have a family to go to. Bart tries to cheer her up and in the end,
Gina takes the fall for him, even if he didn’t ask her to. They seemed to end off on a good note but
when she appears later in Season 24’s “Moonshine River” she punches Bart in the face, so it’s
unknown exactly how she feels about him. The two were forced together and they land here in the end
because while she does seem to not like him anymore, she did sacrifice her freedom for him.
With the best out of the way we can now move on down to a slightly worse section of the list,
this is the Gray Area.
Starting off the gray section of our list are Bart and Nicki McKenna. Bart meets Nicki McKenna in the
Season 21 episode “Stealing First Base” when the two fourth-grade classes get pushed together.
Bart is the one flirting with her in this case and tries his best to get together with her,
although at first, she seems disgusted with him. Nicki’s whole thing is that she’s hot and cold
with Bart, at one moment kissing him and the next screaming in disgust. Nicki mostly just confuses
and annoys Bart. She does save his life with CPR and continues to flip flop between hating
and loving him in “Moonshine River” showing she may have some bipolar issues. Nicki, as we said,
did save Bart’s life which stops them from falling any further, but the two are a very weird case.
Next up on our list are Bart and Greta Wolfcastle. Bart and Greta initially get
together in the Season 13 episode “The Bart Wants What It Wants” when Bart saves her
from being bullied. Bart pretty much ignored her during their relationship, calling her too needy,
leading to the two breaking up and then Bart trying to get her back. They don’t date for
very long but Bart and Milhouse end up making Greta not want to date for a while. It’s no
surprise they land in the gray because they are very obviously not very good together.
The couple from Season 20’s “The Good, The Sad and the Drugly”, Bart and
Jenny rank next up on our list. Bart meets Jenny while at the Springfield Retirement Castle and
tries to date her, but upon realizing that she was a really nice person he tries to convince her that
he’s also a good person. He does quite well in tricking her but Milhouse reveals his true state,
causing them to break up. The problem here is that Bart tries to trick Jenny into dating him which
is a really toxic thing, however, there is so much worse to be talked about so they can’t rank lower.
Rounding out the gray section of our list is Bart and Melody Juniper. This is another short-lived
relationship from the Season 22 episode “Flaming Moe”. Bart starts dating Melody not out of his
own volition but is forced to by Principal Seymour Skinner. This is because Skinner
wanted to date Melody’s mother Calliope, which did work out in his favor. However,
this leads to a relationship that is little more than a ploy for a different relationship
and Bart ends it swiftly. But, at the very least it isn’t abusive so, we won’t rank it lower.
But now we can talk about the bottom
of the barrel and get down to the nitty gritty, these are The Toxic.
Starting off the toxic section of our list are Bart and Darcy. Darcy's first and only major
appearance is in Season 18’s “Little Big Girl”. When Bart gets the ability to drive a car again
he ends up meeting Darcy and lying about his age. He definitely seems to care for Darcy, but Darcy
only really dates him because she feels the need for someone to raise her child. She instantly uses
his car and supposed age to do so, even forcing him to drive to a state so the two can marry,
even after she finds out his real age. This is another relationship built on lies,
and Darcy is a bit abusive, such as what happens with the strawberries situation.
She is also amongst the exes that appear in “Moonshine River” that slam the door in his face,
showing they’re not that good of a combination.
The next relationship on our list is between Bart and Annika Van Houten. Annika and Bart
meet in Season 26’s “Let’s Go Fly a Coot”. Now, this is another situation where it’s mostly a
one-sided crush from Bart’s perspective, as Annika is much older than him and is also the
cousin of his friend Milhouse. Annika doesn’t seem to care too much about him and even starts
to get him to smoke, which is bad for him and his health. At the end of the episode,
Bart reveals he doesn’t like her anymore because of her personality which offends her but she
is then sent off back to the Netherlands. The fact that this isn’t a real relationship
is what stops them from falling lower but they are pretty close to the bottom.
Bagging our bronze medal of toxicity are Bart and Jenda. This is the only relationship we will be
talking about regarding the future episodes of the Simpsons as it’s the only known Bart future
relationship, although you can count Sherri/Terri in Barthood. Jenda first appears in the Season 16
episode “Future-Drama” as Bart’s then girlfriend in highschool, going to the dance together.
Bart and Jenda have an on-and-off relationship throughout the multitude of future episodes.
She breaks up with him in Future Drama because he decides to give up his scholarship to Lisa,
she gives him ultimatums, and although they get back together and have children,
she ends up divorcing him. However, we do have to give her this, she does try her best to keep Bart
in their children’s lives, despite how bad their relationship is, and she tries her best to be a
good person in their interactions. They only grab bronze because it’s obvious they’re bad
for each other and shouldn’t be together, but they seem to get along well enough.
Stealing the silver medal of toxicity are Bart and Shauna Chalmers. Shauna has been a recurring
character on the show since surprisingly late in the show’s run, first appearing in Season
20’s “The Good, The Sad and The Drugly”. However, the episode we’ll be focusing on
is Season 23’s “Beware My Cheating Bart”, where Jimbo hires Bart to chaperone Shauna while Jimbo
does stuff without her. Shauna ends up falling for Bart after he stands up to protect her. Bart
convinces Shauna to leave Jimbo because he doesn’t respect her, and she flashes her chest to him,
which is sort of illegal. Lisa, the smart one, actually forces the two to split up because it was
the best for everyone, especially considering the age gap. Shauna and Bart do kiss once more later
on in the Season 25 episode “What to Expect When Bart’s Expecting” which shows the two actually
have a decent relationship still, which stops them from falling lower. Considering their age gap, the
illegal actions on Shauna’s part, and the slightly coercive circumstances, we have to rank them here.
Grabbing the gold medal of toxicity are Bart and Jessica Lovejoy, Bart’s earliest real
relationship. Jessica’s first and only real major appearance is Season 6’s “Bart’s Girlfriend” where
she is the titular character and antagonist. Jessica is the daughter of Reverend Lovejoy and
is supposedly a perfect angel, however, it becomes obvious that this isn’t the case because not only
is she attracted to Bart’s bad boy persona and Jessica is just as bad. At first, it seems like
this would make them have a very good relationship but then Jessica frames Bart for a crime she
committed. She then uses her status as a “perfect angel” and Bart as a “bad boy” to frame him. This
causes Bart to lose interest in her and then tries to frame her in response. However, two wrongs
don’t make a right, and these two are really bad for each other, hence their gold medal ranking.
But, don’t leave yet because we do have some sinner medals to hand out.
Taking our Darwin medal is Bart and Melody,
who were forced together and Skinner should have seen this coming.
Our Lust Medal goes to Bart and Shauna,
with one of the biggest moments being that she flashed her chest at him.
Obvious, Bart and Laura take out Envy Medal,
because Bart is obviously envious of Jimbo for being able to date Laura.
The Sloth Medal goes to Bart and Annika, because all Annika really
does is lounge around and use Bart to buy cigarettes and e-cigarettes.
Taking our Pride Medal is Bart and Jessica,
but mostly Jessica, who uses her status to frame Bart, which takes a lot of pride.
Finally, our Wrath Medal goes to Bart and Darcy,
where we only really need one word to explain this: strawberries.
But let us know in the comment section if you agree with our
ranking. And tell us what we should cover next. Remember to hit that notification
bell and binge more of our videos. But most importantly, stay wicked.