There was no way this relationship wasn’t going to send shivers down the spines of viewers. Even ignoring the age gap, the circumstances of the relationship will have you worried. McDowell, played by Charlotte Ross, is trying to bond with a daughter she had to give up, and that maternal instinct attracts Sipowicz, who is a new widower with a young son.
Executive producer Bill Clark said that the relationship was like walking onto a minefield. Every single beat was obsessed over while writing and filming. “I can say I don’t think in all of the years on the show any decision has had as much effort put into it like this one.”
Carrie and Aleksandr Petrovsky in “Sex and the City”
The relationships in “Sex and the City,” as well as the show as a whole, are hardly realistic. One of the relationships was distasteful to almost everybody, and it was the relationship between Carrie (Sarah Jessica Parker) and Aleksandr Petrovsky (Mikhail Baryshnikov), who was also known as The Russian.
He's old enough to be her father, and he does nothing but put down her lifestyle and career. Nobody was rooting for the relationship to succeed, even before the show heightened the relationship to even more uncomfortable levels, as the show is wont to do. The relationship became ugly, sad, and strangely realistic.
Alan and Kandi in “Two and a Half Men”
The relationship between painfully boring Alan (Jon Cryer) and dimwitted beauty Kandi (April Bowlby) was never played for anything other than a laugh, and it barely got that. She was a young woman who had already been with Charlie (Charlie Sheen), and the age gap is just one of the things the show tweaked.
Kandi also compared the “skills” of Charlie and Alan and seeing how the two are brothers; it just continued to get worse and worse. Incredibly, Alan and Kandi get married, yet the relationship later dissolved.
Debra and Lundy in “Dexter”
We shouldn't be all that surprised that a show that made us care for a serial killer had some other offbeat writing choices. In that manner, the relationship between Debra (Jennifer Carpenter) and Lundy (Keith Carradine) was well-regarded by fans. While Lundy was old enough to be her father and was even a superior officer, if at a different enforcement agency, at least he wasn't a crazed killer.
It wasn't even the weirdest relationship for Deb, seeing as how she hooked up with her own brother, if at least after discovering he wasn't her biological brother. At the very least, the writers tried to make the relationship about “deep love.”
Lord Walder Frey and his Wives on “Game of Thrones”
Unlike most of the other members of this list, we aren't meant to sympathize with or agree with Lord Walder Frey (David Bradley), a lecherous old man who continually takes new wives as previous ones get too old.
The first time we meet him on the show, he introduces Caitlyn Stark to his newest wife, Joyeuse (Kelly Long), who is a mere fifteen years old, standing meekly next to her nearly-ninety-year-old husband. He also has other wives. Among the gross men of “Game of Thrones,” Frey stands out, and that's saying something.