In The Simpsons, almost every major character has had at least one romantic subplot,
and in the case of Lisa Simpson, she’s had quite a few relationships to talk about. From dopey
children of police chiefs to school bullies and everything in between,
we’d be remiss if we didn’t talk about Lisa’s love life. More than
a few episodes have been dedicated to diving into her repertoire of fun and recognizable
suitors. But which of these Lisa Lovers are the best, and which are less than likable?
I’m Brad with WickedBinge and this is Lisa Simpson Relationships: Healthy to Toxic.
We can start off by talking about the best relationships on our list, these are The Healthy.
Earning our gold medal of health is Colin. Colin is a young man from The Simpsons Movie,
being an Irish environmentalist and musician that Lisa falls in love with. He is shown to be very
sweet and caring and obviously cares for Lisa and her goals. He even tries his best to keep
her okay during their escape with a new song he wrote for her. The two get along very well,
and even despite the fact that he only ever appears in cameos after the movie,
he is by far the best relationship for Lisa.
Next, we have the silver medal of health which goes to Thelonius. Thelonius is a short lived
romance from the iconic Season 12 episode “Trilogy of Error” when Lisa goes to the wrong Springfield
Elementary, she meets Thelonius. They don’t meet for long and it is a love at first sight
thing for sure, but the two are quite sweet for the short time we witness their relationship.
Thelonious even tells Lisa that she shouldn’t sacrifice her grades for romance and they’ll
meet again in high school, which shows he wants Lisa to have her priorities straight.
Taking the bronze medal of health is none other than Nelson Muntz. Nelson is a recurring
bully character who starts to date Lisa in “Lisa’s Date with Density”. Nelson culls his
bully tendencies as best as possible, trying to change for Lisa, even if it doesn’t last
very long. Sure, the two break up because Nelson helps the other bullies throw expired coleslaw
at Skinner’s house. Throughout the rest of the series their relationship is mentioned,
and in episodes that look into the future, he’s one of the more common relationships she ends up
in. Nelson is a good guy at heart, at least when he’s around Lisa and shows he still cares about
her in other episodes like “The Great Simpsina” where he threatens to burn ants to spite god if
Lisa doesn’t come back. Nelson cares very deeply for Lisa and this shows in later episodes. The
episode “Barthood” shows one version of the future, in which Lisa saves Nelson’s life with
a new surgery she helped create and the two get together. If it wasn’t for the fact that Nelson
has to change himself, both in the initial episode and in “Barthood” to “prove” that he is worthy of
Lisa in some way or another, the two would likely rank higher. Nelson does have to change himself
to be “worthy” of being with Lisa which isn’t the greatest, but, Lisa seems to be doing it for not
only Nelson’s wellbeing but to give back to his former victims. So while we don’t love the idea of
someone having to drastically change themselves if they want a relationship, Nelson seems to
benefit from it. However that doesn’t stop the two of them from not grabbing a higher ranking,
because it’s still not the greatest for either of them to try and force change.
As we move down the list we get to Jack DeForest. Jack is another child at Springfield Elementary
who appears during the Season 27 episode “The Burns Cage”. He auditions to play Rick in the
school’s Casablanca play and easily takes the role, with Milhouse being his understudy. He
doesn’t date Lisa for very long, but he has amazing chemistry with her on stage,
even if he was pretending to be Milhouse at the time. Sure, he gets kicked out of
the play because he beats up the bullies who are sent after him. But, despite all this,
he and Lisa are quite nice to each other and by the end of the episode, he goes on a treasure
hunt, while seemingly still dating Lisa. The only main problem with him is a lack of real romantic
moments with Lisa. Other than that, he definitely has a pretty good relationship with Lisa.
Next up on our list is Brendan Beiderbecke. Brendan is an 11-year old jazz pianist
voiced by Ed Sheeran in the Season 29 episode “Haw-Haw Land”. He meets Lisa at a STEM event,
and the two very quickly realize how much they have in common and they start to briefly date.
Like a lot of her other relationships, while it’s sweet, it doesn’t last very long as by the end of
the episode Brendan has to transfer to another school. The two were very similar to Lisa and
Colin’s relationship, the main difference being that Brendan never really shows the same sort of
affection towards Lisa as Colin did, despite this, the two are quite good for each other,
even if they don’t particularly last long. Why he lands lower than Jack is simply because while they
have a lot in common, Jack seems to like Lisa more than Brendan, but it could go either way.
Rounding out the healthiest section of our list is Lucas Bortner. Lucas is part
of the Season 25 episode “Luca$” where he is training to be a competitive eater. Lucas,
unlike other characters, accepts Lisa for all her faults and this leads to Lisa and
Lucas getting quite close. Lucas continues to train and Lisa is more than willing to help him,
however, they don’t stay together long. Like other times, Lisa has a so-called “vision” of
her future with Lucas and she decides against dating him, deeming him as too slovenly and
like her father for her to date him. So, because of this vision and Lisa’s sort
of pretentiousness regarding it, they barely survive enough to land in our healthy section.
We’ve now moved onto the lesser loved
relationships for one reason or another, these are The Gray.
Starting off our gray area is the short-lived Milhoose. Milhoose is a small character in the
Season 21 episode “Boy Meets Curl”. He is the Canadian version of Milhouse and acts pretty
much the same as him, instantly crushing on Lisa. However, this is a very one-sided relationship,
as it’s only a crush from Milhoose that is unrequited by Lisa. However, he ranks here
because he doesn’t do all of the weird crazy stuff that Milhouse does that makes him rank lower.
One of Lisa’s most iconic romances is Ralph Wiggum. Ralph is another second-grader that
is in Lisa’s class, and during the Season 4 episode “I Love Lisa”, the two briefly get
together. This is because Ralph didn’t have any Valentine’s Day cards from the other students so
she gives him the now iconic “I Choo-Choo-Choose You” card, which leads Ralph to try and date her.
The two are together for a short time, mostly thanks to Chief Wiggum. This gets to the point
where Ralph has tickets to the Krusty the Clown show, and Lisa really doesn’t
want to go with him because she doesn’t like him. She publicly blows up on him,
breaking up with him on public television which is not a great look for her. Ralph mentions their
relationship at many other points in the show, which shows he knows enough to recognize what
their relationship is. The end of the iconic episodes has the two become friends once more,
which shows that despite the very rough breakup and amazing play,
the two can manage to still be friends. Ralph and Lisa can’t really rank too much lower,
only because Ralph’s understanding of things is questionable at best and downright dumb at worst.
Her other iconic “relationship” is with Milhouse Van Houten. Milhouse and Lisa have never actually
fully dated on the show, but Milhouse has had a crush on Lisa for almost as long as he’s been
a character. Milhouse has tried to date Lisa in a myriad of different ways, whether that be
public or private, but they’ve never fully gotten together, save for in the future.
The future version of Lisa very obviously picked Milhouse as a last ditch effort, but despite this,
they have a daughter together and the two seem to care about each other to a degree. Although,
Lisa only shows real love for Milhouse when he becomes a zombie, which somehow makes him better.
Milhouse gets immensely jealous and paranoid when with Lisa and it’s not great for Lisa. However,
Milhouse very obviously deeply cares about and loves Lisa,
even if Lisa doesn’t feel the same way towards the blue-haired boy. Hence why
we don’t rank them any lower, even if they might deserve it a little bit.
Rounding out the Gray area of our list is rich boy Blake Black. He appears as part of the Season
28 two-part special “The Great Phatsby”. He’s a rich kid who lives in the very rich part of town
that Homer and family go to while Homer tries to get Mr. Burns his riches back after he lost them
all to mysterious music mogul Jay G. Lisa gets mad at Blake for cutting in line and when he
offers to buy everyone a cone, Lisa says no. This intrigues Blake because he’s never “dated anyone
with morals” which is why he becomes so interested in Lisa. He tries everything to appeal to her
morals when they go on their “dates”, although each time he fails miserably. Lisa abandons him
for another boy who has the money and tickets to the pony show she was going to, which shows
that unlike Milhouse, Lisa doesn’t care about Blake in the slightest, hence their ranking.
But, now we can start talking about
the worst of the relationships in the list, these are The Toxic Relationships.
Starting off the toxic area of our list is Jesse Grass. Jesse is an environmentalist from the
Season 12 episode “Lisa the Tree Hugger” and is a so-called “level five Vegan” which means he won’t
eat anything that casts a shadow. Jesse leads a community of vegans known as “Dirt First” and
Lisa has a heavy crush on him. Jesse leads Lisa into tying herself to a tree and supposedly dying,
because she wanted to prove herself to him. He is known for protesting fast food places like Krusty
Burger in a cow suit and trying to convince others to join Dirt First. The main issue with this
relationship, beyond the whole supposedly dying and subsequent lying to Jesse from Lisa, is the
age-gap. Lisa is an eight year old, and yes, she’s dated and had crushes on older kids before, but
Jesse is a teenager. Not like a thirteen year old but he looks and acts much closer to the sixteen
or seventeen year old area, which is a massive age gap. That would make him double Lisa’s age at this
point in the show and makes it completely unlikely the two would ever date. The one saving grace is
that Jesse doesn’t show any romantic inclination towards Lisa and it’s just a one-sided crush.
Up next in the toxic section of our list is Luke Stetson from the least christmassy
Christmas episode of the Simpsons. Luke appears during the Season 14 episode “Dude,
Where’s My Ranch”. Luke is a 13 year old kid who works on a dude ranch out in the desert that
the Simpsons go to later on in the episode. Lisa has an intense crush on this kid, and while Luke
seems to like her to a degree, Lisa completely ruins her chances. Because, near the end of
the episode she mistakes a conversation between Luke and his sister Clara Stetson as romantic.
This leads Lisa into trying to put Clara on the wrong path, which almost leads her to her demise,
this leads Luke to actively hate her despite her supposed apology to the boy. Luke seems
like a good guy for the most part, but even that doesn’t stop them from falling here.
Bagging our bronze medal of toxicity is Edmund. Edmund is a major character from
the Season 22 episode “Treehouse of Horror XXI”, specifically in the segment called “Tweenlight”.
He appears throughout the segment, saving Lisa’s life multiple times, causing Lisa
to develop a crush on him. Edmund then takes Lisa out into the forest, revealing his fangs,
and the fact that he’s a vampire, this is when Lisa reveals she’d be willing to live forever as
a vampire if he wished to bite her. However, there are a few issues with this, firstly, Lisa would
then be physically eight years old forever, which she obviously doesn’t like. Secondly,
like we talked about with Jesse, the age gap here is much more important to take into account,
Edmund is 400 years old, despite his eight year old body, that doesn’t change the fact
that he’s been around for 400 years, which makes this relationship even more creepy. Finally,
the most major problem is that Edmund tries to forcibly bite and transform Lisa after she already
said she didn’t want to become a vampire, which is a barely veiled allusion to assault. However,
beyond this, Edmund seems sweet enough that he doesn’t fall lower, but he was close.
Snatching our silver medal of toxicity is none other than Hugh Parkfield. Hugh is the
main romantic interest from Season 6, Episode 19 “Lisa’s Wedding”. When Lisa goes to a county
renaissance faire she meets a fortune teller who tells her that she may be able to tell
her the true future of Lisa’s love life. Said love life is supposedly going to end with Hugh
Parkfield. Hugh is a British student who goes to the same college as Lisa, the two of them meet in
the school library when the two both need the same book for a class. Hugh and Lisa absolutely despise
each other at first and it’s quite obvious that they wouldn’t work together well in a romantic
relationship. Even though their relationship has a glorious start, it very quickly goes south as
they prepare for the titular wedding. Hugh heads to America to meet Lisa’s family and while Hugh’s
family loves Lisa and she makes a good impression it’s quite the opposite for The Simpsons.
The Simpsons mean well but end up disrespecting and disgusting Hugh, which leads to him trying
to pull Lisa away from them. Lisa does end up growing a spine and dumps Hugh after he
utterly refuses to take part in only one of her family’s traditions with Homer’s cufflinks,
which shows that her true love is actually her family. Lisa and Hugh are terrible for each
other and it’s no surprise that they don’t work out. The only reason they don’t grab gold and we
mean the only reason, is because at least it’s not a manipulative scandal like our final one.
Speaking of, grabbing the gold medal of toxicity is none other than the nastiest newbie, Nick. Nick
is from the Season 23 episode “The Daughter Also Rises” where he makes his one and only appearance,
voiced by Michael Cera. Lisa meets Nick in a special restaurant and Nick immediately
makes himself seem much better than he actually is. He tries to impress Lisa with a suave and
confident personality that is in fact a facade used to trick Lisa. Nick tells her not to tell
him her name since he wants the first place he hears it to be “special”. He also manages
to come around at the best possible time as his presence allows Lisa to take her focus off the
bad events happening around her. The couple seem to be quite good at first, and it isn’t
until Grampa says that the two need to kiss underneath a tree to seal their union forever.
This then goes to show off Nick’s actual insecure personality as he isn’t ready to commit to a
relationship. By the end of the episode, Nick reveals that “god gave him a gift to lie to the
ladies” showing that not only was he knowingly lying to Lisa, but also had done it multiple
times in the past. Nick is manipulative beyond belief, able to convince Lisa that he loves her,
when he actually doesn’t, which makes this by far the worst relationship on our list by far.
But don’t touch that dial and don’t change
that channel because we’ve got some glorious Sinner Medals to hand out.
Earning our Darwin Medal for dumbest character goes to Ralph Wiggum,
undoubtedly. Ralph is so far behind the rest of his class that he can’t be trusted with
glue or safety scissors, however, he does seem to be emotionally intelligent to some degree.
Milhoose is the one who takes our Lust Medal for obvious reasons,
because he falls in love with Lisa upon just meeting her for the first time.
Up next, our Wrath Medal goes to Nelson Muntz. Nelson is a bully,
wanting to punch and attack those around him, especially when Lisa is getting harmed.
To no one’s surprise, Lucas Bortner takes our Gluttony
Medal. Lucas is known for trying to become a competitive eater, so it’s no surprise.
Taking our Greed Medal is none other than Blake Black,
this is simply because of how rich he is and how much he is willing to throw around.
Finally, our Pride Medal belongs to Nick, who believes it’s not only a good thing,
but a gift to lie to women. 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.