When it comes to Family Guy, making a list of any kind of questionable choices is a challenge. The main and secondary characters are non-stop bad idea machines. But the most fertile grounds for some of the worst ideas in the series are relationships.
No one in that entire show seems to know how to get it right. Almost every single dating scenario that has happened on Family Guy has resulted in some sort of train wreck. Keeping that in mind, there are more than a few that stand out as the absolute worst of the worst. And those ones just never should have happened.
Brian Griffin And Jillian Russel-Wilcox
Brian Griffin has had a shocking number of relationships throughout the run of the series, and he treated a lot of them very poorly. It's a wonder that anyone is willing to out with him.
One of his longest-standing relationships was with Jillian. She wasn't the smartest person on the show, but she was possibly the nicest. Jillian could have easily done better than Brian though he could not do better than her.
Joe Swanson And Nora
Like most of his neighbors, Joe is prone to making some pretty terrible decisions. Making matters worse is the fact that he actually listens to people like Peter, Quagmire, and Cleveland. The only way someone should take their advice is if that person is doing the opposite of what they say.
After Joe's wife Bonnie cheated on him, Peter told Joe he should cheat on her with his partner, Nora. It was an unbelievably terrible idea that almost destroyed Joe and Bonnie's marriage.
Bonnie Swanson And Brian Griffin
As previously mentions, Bonnie had committed her own indiscretions in her marriage to Joe. A big on was briefly leaving Joe for Brian. They fell in love quite quickly, then ran off together.
This hurt Joe unbelievably as he considered Brian to be a friend. But as one would expect, Bonnie and Brian fell out of love equally quickly and their doomed relationship came to a mercifully quick end.
Stewie Griffin And Penelope
Stewie is by far the most malevolent force on the show. While he's somewhat toned down his attempts to kill Lois in recent years, he's still a heavily armed toddler with more brains than common sense.
When Stewie met Penelope, he found his Machiavellian equal. They committed many horrific acts around the world together. The breaking point in their relationship came when Penelope tried to kill Brian but Stewie intervened.
Cleveland Brown And Loretta Brown
When Family Guy first hit the airwaves, Peter's neighbor and close friend Cleveland was married to Loretta. Their divorce led to Cleveland getting remarried and leaving town, which launched his spinoff series.
The relationship between Cleveland and Loretta was at it best when it was nonexistent. The only positive thing that came from that experience was that it eventually ended.
Chris Griffin And Alyssa
When it comes to love, Chris makes a lot of bad choices. His record is dismal, to say the least. But one of the worst, and shortest, relationships he had was with a young woman named Alyssa.
Alyssa was a member of the Young Republicans who needed help killing Brian's pro-gay marriage petition. She attempted to use Chris's attraction to her to manipulate him into assisting her. It didn't work in the end as the Mayor's office intervened.
Stewie Griffin And Olivia Fuller
The rivalry between Stewie and Olivia has defined both of them in some strange ways. They have been at odds on numerous occasions over their respective stage careers. But this naturally led to them becoming a couple and "getting married."
Their old problems quickly resurfaced and caused numerous problems between them. Ultimately, their time as a couple came to an end when Stewie set their playhouse on fire. Knowing Stewie, that was probably the best possible outcome.
Chris Griffin And Connie D'Amico
Connie the stereotypical high school girl. She's the super popular head of the cheerleading squad who is incredibly mean and cruel for no reason, particularly to Meg who is almost always the target of Connie's harassment.
In one episode, Connie was challenged to make Chris popular by dating him. The irony of the situation was that she developed real feelings for him but made him too popular for her to date. Their relationship came to an end.
Meg Griffin And Neil Goldman
Without question, Meg is the biggest female outcast in her school. And if she has a male counterpart, it's Neil Goldman. They are both such massive losers that they almost seem like a match made in Heaven.
Instead, any romantic moments between them have been huge awkward failures. Meg really isn't interested in Neil, which is something he is not willing to listen to. He just keeps pursuing her, and ultimately embarrasses them both.
Peter Griffin And Lois Griffin
This relationship isn't so cut and dry. At the core of the series is the marriage of Peter and Lois, for better or worse. And anyone who has watched the series knows that it's mostly for worse, mostly thanks to Peter's constant shenanigans.
Their marriage is not great. Lois loves Peter but it's almost impossible to understand why. He's not a particularly good husband or father. She could definitely do better than him, and that doesn't include dating either Brian or Quagmire.