Does Obi-Wan Flirt With Asajj Ventress & Are They Star Wars' Weirdest Ship?

If you've only watched the "Star Wars" movies, you might not know how much of a flirt Obi-Wan Kenobi was in his heyday. But in "Star Wars: The Clone Wars," you may notice a different side of the sagely Jedi Master — the romantic side. One of the biggest storylines in all of "The Clone Wars" involves Satine Kryze, the Duchess of Mandalore, with whom Obi-Wan has an extensive and complicated history. While still just a Padawan under Qui-Gon Jinn, Obi-Wan served as Satine's bodyguard, and their relationship progressed beyond just work.

Through his relationship with Satine, we see how Obi-Wan might have turned out differently had he not adhered so strictly to the Jedi code. But, of course, the Mandalorian duchess isn't the only woman Obi-Wan tries to rizz up in the animated series. That's because every time he encounters the Sith assassin Asajj Ventress, it always turns into a bizarre flirt-off.

You could write this off as a battle tactic to throw Ventress off her game (he is very handsome, after all), but there's no denying that Obi-Wan is at his absolute flirtiest when dueling Ventress. Their dynamic only becomes more complicated later in the series when she abandons Count Dooku and the Separatists, leading to some charged team-ups with her Jedi rival.

Obi-Wan and Ventress have a really strange dynamic

"Ventress ... and here I thought this mission would be unpleasant." That's how Obi-Wan greets the Sith assassin in the "Clone Wars" movie. "The pleasure's all mine, my dear Obi-Wan," she responds. Clearly, these are two people who loathe each other. Obi-Wan frequently refers to her as "my darling" in the movie and the "Clone Wars" series, and their fights are packed to bursting with innuendos.

Later on, after Ventress is betrayed by Dooku and strikes out on her own, she saves Obi-Wan from the rogue Sith brothers Maul and Savage Opress. She stirs him from a coma, and after he gets his bearings, he remarks, "What a lovely sight to wake up to." "Don't flatter yourself, Kenobi," Ventress fires back. "You've never been much to look at. Especially now."

It's easy to see why some fans might ship these two. After all, who doesn't love a good enemies-to-lovers arc? However, Ventress ultimately sets her sights on another Jedi, the emotionally troubled Quinlan Vos. The canon novel "Star Wars: Dark Disciple" details the forbidden romance between the two, which ultimately leads to Ventress dying in a tragic fashion. It seems that the oft-shipped Obi-Wan and Ventress love story just wasn't meant to be, no matter how much palpable sexual tension they have.