Family Guy has been going strong since 1999… and throughout that time, plenty of characters have
come and gone. But one of the most iconic characters outside of the Griffin family
is good old Glenn Quagmire. Local pervert, comical sex offender,
dog hater and pilot… Quagmire is a character many people love and despise.
And one thing is for sure. Quagmire has had a lot of…
strange… relationships. Many of which go well past our usual “healthy to toxic criteria”.
I’m Kifinosi with WickedBinge and this is Glenn Quagmire Relationships:
Healthy to Toxic… to Disturbing.
First off, we’ll be discussing different types
of relationships. Not simply the romantic or intimate ones.
Secondly, as the title suggests, Glenn has very few healthy relationships, and toxic is not really
a way we’d describe most of his relationships on this list, so we’ll be skipping the gray
area altogether. So, in a way… “Toxic” is kind of Quagmire’s “average”... Where the furthest
end of our spectrum will be reserved for his relationships are downright dark, disturbing
or illegal. So just a heads up, in case anyone is uncomfortable with the discussion of those things.
There aren’t very many, but we’re starting out by talking about our
best relationships, these are The Healthy.
Taking our gold medal of health is Quagmire & Brenda. Brenda is Quagmire’s younger sister who
has appeared in a couple of episodes, initially in the Season 8 episode “Jerome is the New Black”.
In this episode, she comes to stay at Glenn’s house because she is being beaten by her fiance
Jeff. Quagmire clearly cares for his younger sister and will do just about anything for her,
such as in the entirety of Season 10’s “Screams of Silence: The Story of Brenda Q”. In this episode,
which is Brenda’s most major appearance, we see the full extent of Jeff’s abuse.
Quagmire tries his hardest to solve this problem in a peaceful way,
trying to convince Brenda to leave him. This doesn’t work so Quagmire jumps to murdering
Jeff to save his sister. It’s no surprise they rank here… Although it may be odd to start out
our Healthy section with a relationship that resulted in a murder, but… It’s Family Guy. And
there aren’t many people you’d murder another man for, so they definitely have to take gold.
Earning our silver medal of health is the relationship between Quagmire & Cheryl Tiegs.
Cheryl Tiegs is one of the Quagmire’s first relationships and his first celebrity crush.
As early as Season 3’s “Emission Impossible” we can see this because
Glenn has a poster of Tiegs in his home. In Season 4’s “The Perfect Castaway”
Glenn even mentions that if he were blind every woman who he slept with
would be Tiegs. The Season 8 episode “Jerome is the New Black” reveals the full extent of their
relationship because they were in a happy serious relationship when Glenn was young.
The two broke up because of that damn James Woods, which apparently led to
the perverted man that Glenn had become, due to feeling emptiness in his soul.
This is used against him later by Brian who starts dating Cheryl Tiegs just to mess with him.
This is no doubt one of his healthiest relationships and it’s sad that this relationship
failing is what led Glenn to become the man that he is.
Taking our bronze medal of health goes to Quagmire & Ida. Ida’s first appearance in
the Season 8 episode “Quagmire’s Dad” is where she comes to Quahog to be honored
for her military service. This is also when she gets her sex change
and fully embraces her true self. Quagmire is initially grossed out and against this,
but after a while he manages to accept her and love her once more.
Ida does embarrass Quagmire at times, talking about her operation or when she was sleeping
with Brian, but she tries her hardest to be by Glenn’s side and he tries his best as well.
Later episodes such as Season 12’s “Quagmire’s Quagmire” show that she will go to the ends of
the earth to find her son and Season 16’s “The Unkindest Cut” ends with Ida giving Glenn her old…
”equipment” after Glenn gets his bitten off by a shark.
Next up on our list is the relationship between Quagmire & The Guys. Quagmire has been friends
with Peter and Cleveland for a long time and became quick friends with Joe since his first
appearance. Ever since then, this group has done many things, even after Cleveland left the group
for his own show. They care about each other, such as in Season 13’s episode “#JOLO” where
they stop Joe from jumping off Niagara falls because they care about him that much. Sure,
they’re great friends, they drink together all the time, and have been since Season 1. Some episodes,
such as Season 10’s “Forget-Me-Not” show that they would still be friends with amnesia, showing they
are really good friends. But there are also plenty of episodes where the exact opposite
is also true, they fight a lot and that’s kind of the reason they don’t grab a medal.
Episodes like Season 12’s “Brian’s a Bad Dad” has Peter and Quagmire shooting each other,
Season 16’s “Foxx in the Men House” has Peter abandon them because he found somebody cooler
and the season 15 episode “Passenger Fatty-Seven” is all about Quagmire’s friends thinking less of
Quagmire because of the Autopilot feature. But while they fight, they always stick together
in the end, meaning they definitely deserve to be in the healthy section.
Next up on our list is Quagmire & Anna Lee. In the Season 8 episode “Quagmire’s Baby”,
we are introduced to Anna Lee, the titular baby. She was left on Quagmire’s doorstep
during a garage sale he had by one of Glenn’s one-night stands. He tries his
best to be a good dad to the young girl but it shows to not be a very easy situation for him,
especially since she continually interrupts any of his romps.
Now, he initially gives her up to the foster care system because of
the aforementioned interruptions but he regrets this decision. He even tries to get her back but
realizes she’s happy with her new family, so he doesn’t get in the way of this happiness.
Up next on our list are Quagmire & Sujin. Sujin appears in the Season 14 episode “Candy Quahog
Marshmallow!”. It turns out, that she and Quagmire had dated long ago when he was in Korea as part
of a romantic soap opera. The two fell in love while working on the show and they seemed to
be quite loving, especially compared to some of Quagmire’s other relationships as he isn’t just
using her for relief. He was even willing to throw away his old life to live with her and her cats,
showing he really cared for her. Obviously, this doesn’t work out because Glenn finds
out that her entire family would be living in close quarters to them and he doesn’t want to
deal with that. But all in all, this is one of his best relationships overall, hence the placement.
Rounding out the healthy section of our list are Quagmire & Courtney.
This one is going to sound pretty bad on paper but we have to remember this is Family Guy logic.
Courtney’s from the Season 17 episode “No Giggity, No Doubt”; who Glenn meets at a high school prom.
Now, Glenn makes sure to ask her how old she is, and she confirms
she’s 18... But before anything happens, Glenn finds out they’re related, and after this point,
he switches to trying to be a good father. This starts with him offering for her to live
with him at his house and changes quite a lot since he takes the dad thing very seriously.
Now we get into the meat and potatoes of this list, these are the Toxic Relationships.
Starting off the toxic section of our list is the relationship between Quagmire & Lois. This has
been explored in a multitude of episodes, most recently in Season 20’s “The Lois Quagmire”.
Quagmire has been heavily interested in Lois for a long time, despite her and Peter having
been married for quite a while. Glenn is shown to be attracted to her, spying on her at times,
and hitting on her at others. Now, he tells Brian in one episode that he’s only really attracted to
her body, to show that he’s better than him because he’s honest. But despite this, on
multiple occasions, Lois and Quagmire get together in one way or another, the Season 8 episode “Big
Man on Hippocampus” has the two get together when Peter has amnesia, and he’s shown to be quite good
for her. In another episode that takes place in an alternate timeline, Season 5’s finale “Meet
the Quagmires” shows that if Peter and Lois hadn’t gotten together, she would have married Quagmire.
The next relationship on our list is between Quagmire & Carrie. This comes from the Season
20 episode “Must Love Dogs”. Quagmire meets Carrie when she and her niece come to his
house during trick or treat. This leads to Quagmire and Carrie hitting it off and they
do seem to care about each other until Glenn learns she loves dogs. As we know,
Glenn doesn’t particularly like dogs so he ends up repeatedly lying to her to try and get with her.
This leads to him proposing to her through Brian and having to deal
with her intense amount of dogs and the problems that arise from that.
The next relationship on our list is between Quagmire & Loretta. The
entirety of this relationship is explored in Season 4’s “The Cleveland-Loretta Quagmire”,
where Loretta, Cleveland’s wife, sleeps with Glenn. It’s said because Cleveland’s
generally emotionless personality doesn’t excite Loretta anymore so she instead gets with Glenn.
This obviously doesn’t last long as many of Glenn’s relationships fall apart similarly,
but this relationship is predicated on the betrayal of a friendship. Even
though Glenn does feel bad about this, so we have a very hard time placing this
relationship, hopefully, this fits the general vibe we’re looking at.
Up next are Quagmire & Monica. A relationship from the Season 17 episode “Island Adventure”.
Monica is a middle-aged woman that Glenn has quite a lot of trouble getting with. He keeps getting
shot down by her, leading to him going to Lois for advice which he uses. However, he very quickly
disregards her to get with other women, which Lois gets very angry about. This is a very short
situation, but the fact he just tosses her aside, while not a surprise, definitely ranks them here.
Iconic for all the wrong reasons, the next relationship we needed to talk about is Quagmire
& Brian. Quagmire and Brian initially seemed to be quite good friends due to Brian being Peter’s dog,
but as of Season 8 and our favorite episode to talk about apparently “Jerome is The New Black” it
is shown that Glenn hates Brian. Glenn hates Brian for a hundred and one reasons, including but not
limited to: constantly hitting on Lois, driving a Prius, looking down on religious people, and being
untrustworthy. While initially not despising Quagmire, this hatred became mutual and episodes
like “Tiegs for Two” from Season 9 show that Brian is willing to date Cheryl Tiegs just to mess with
Quagmire, and the aforementioned Season 8 episode “Quagmire’s Dad” has Quagmire brutally assault and
attack Brian for having relations with Ida. Even more recent episodes like Season 20’s “Must Love
Dogs” explore this relationship in depth. With Quagmire using Brian to get into bed with a woman,
Brian even forces the two to get married much to Glenn’s chagrin. We’ve only scratched
the surface of this relationship but it definitely deserves this spot on the list.
But, now we get down to the worst possible relationships, these are The Disturbing.
Quite short but next on our list is Quagmire & Sandra from the Season 15 episode “The Dating
Game”. When Glenn finds out about the hookup app Tinder he becomes a crazed husk of a man unlike
himself that Peter and the gang have to fix. After fixing Glenn he becomes depressed about what had
happened and feels like he’s lost his spark until he meets Sandra. He immediately tricks Sandra into
sleeping with him by telling her a phony story about his dead twin brother and taking her home,
and like many of Quagmire’s other “conquests”
being based on trickery we can’t in good conscience rank this situation any higher.
One of Glenn’s few marriages, Quagmire & Charmisse is next on our list. In the Season 11 episode
“The Giggity Wife” Quagmire accidentally marries Charmisse, a lady of the night,
while he was drunk. He doesn’t particularly like her too much and tries to break up with
her by pretending to be gay. This doesn’t go too well because she tries to force him into
having gay relations with Peter to prove it. The two eventually manage to split up, but not
after such a terrible breach of privacy, mostly on the part of Charmisse which is quite the change
considering Glenn is usually the one who provides all of the terrible moments in the series.
Another very short one we need to talk about is Quagmire & Tracey Bellings.
In a flashback during the Season 12 episode “A Fistful of Meg,”
it’s revealed that Tracey is one of Quagmire’s earliest relationships. Tracey was a bully who
berated Glenn over his choice of Royal Crown Cola rather than Coke or Pepsi. This led to a
mix of an assault and a sexual encounter that has stuck with Quagmire for most of his life.
Apparently, this was the start of a long abusive relationship that was mostly public.
The weirdly popular Quagmire & Meg relationship ranks next on our list. Now, Meg and Quagmire
interact quite often, being neighbors and Meg being the daughter of Glenn’s best friend,
but they don’t really get together until the Season 10 episode “Quagmire and Meg”. This is
a very weird relationship because despite how they are in every other episode, the “Quagmire and Meg”
episode throws everything out the window. It is obvious throughout the episode that he is not only
doing it exclusively to sleep with her but it’s also obvious that he’s manipulating her throughout
the episode to try and get in her pants. This is disturbing because not only did she just turn 18
but she’s the daughter of his good friend and he’s likely known her since she was a baby.
Up next on our list are Quagmire & Brooke Roberts. This is a relationship that only
appears in Season 4’s “Brian The Bachelor” where both Brian and Quagmire are on The Bachelorette
to date Brooke Roberts. Quagmire is one of the first bachelors to get a rose during the show,
showing that Brooke liked him at least a little bit. However, this falls into the disturbing
category for good reason, because on their private date which was being filmed because
it’s a reality show, he roofied her and tried to take advantage of her. He luckily doesn’t
get to that point because he catches the camera people but he was just about to,
in fact, he ends up in the final two because Brooke is unaware of what happened.
He doesn’t end up winning because he was trying to have a three-way between him,
Brooke, and his own mother, which is a whole other can of worms.
The next “relationship” is a short one, between Quagmire & Jennifer Love Hewett.
In the Season 3 episode “Stuck Together, Torn Apart” it’s revealed that Jennifer Love Hewett is
the niece of Mort and Muriel Goldman who they set up on a date with Peter. At the end of the night,
Lois breaks up the date between Peter and Jennifer and she goes to get drinks. Jennifer
is subsequently drugged by Quagmire via the use of a “roofie-colada” which he orders on most dates
apparently. Now, we don’t see what happens past this but it’s pretty easy to figure out.
Bagging the bronze medal of disturbing are Quagmire & Keira. These two are shown
together very briefly in the Season 13 episode “Quagmire’s Mom”. Keira is a girl that Glenn
meets at Peter’s party who he almost immediately takes home to sleep with when Lois arrives. It
turns out that Kiera was only 17, meaning she was underage, despite saying she was 23. This leads
to him being arrested, although he still sends pictures of the deeds to Joe and his friends,
which is a whole other crime in itself. He was even sentenced as guilty and would have gone
to prison if it wasn’t for his mother. Stealing our silver medal of disturbing
are Quagmire & Joan. Joan first appears in the Season 4 episode “I Take Thee Quagmire”. Peter
wins “Wheel of Fortune” and Joan is the maid he got from the show… She meets Quagmire, and the
two fall in love. This is one of the few times where Quagmire seems to actively love someone
instead of being the personification of our lust medal. Not too long after he even proposes to Joan
and the two get legally married, and while they seem happy at first, Glenn very quickly
falls back into his lustful ways and tries to divorce her, which leads to her threatening to
murder Quagmire and then kill herself. Quagmire then tries to fake his death multiple times
and only stops when Joan accidentally kills herself by touching Death’s arm. Disturbingly
he then asks Death to leave the body behind for five minutes, supposedly for him to
“do things” with. So this relationship is pretty much on another level as far as being screwed up.
Finally, grabbing the gold medal of disturbing relationships
are Quagmire & Sonja. In the Season 12 episode “Quagmire’s Quagmire”, we are introduced to
Sonja. Glenn meets Sonja when he goes to return a laptop that has stopped functioning, it turns out
that she is just as lustful as he is. The two initially hit it off due to being so similar,
but it very quickly goes south after this. Sonja drugged him to make sure she could sleep with
him on their first night and Glenn initially thinks he’s in love with her because of this.
Sonja slowly becomes worse and worse, humiliating him at every turn and even kidnapping him. She
even attempts to shoot Joe when they try to save Quagmire. As the episode title implies, Sonja ends
up being just as disturbing as Quagmire himself. 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.