Star Wars’ new TV show, Star Wars: Tales of the Underworld, makes me wish we could see Obi-Wan Kenobi reconnect with another pivotal character from his past. Obi-Wan Kenobi is a central character in the Skywalker saga, having personally trained – and partially raised – Anakin Skywalker before he fell to the dark side, fought in the Clone Wars as a Jedi General, and later saved and trained Anakin’s children, Luke Skywalker and Leia Organa. Obi-Wan had many friends and enemies, most of whom he encountered again at a later point in his life.

He's had reunions with Darth Vader in the Obi-Wan Kenobi series and the original Star Wars film, his lethal rivalry with Darth Maul, which started in Star Wars: Episode I – The Phantom Menace, continued in Star Wars: The Clone Wars and ended in Star Wars Rebels, and there was even a time when Star Wars considered having Obi-Wan reunite with Clone Commander Cody in Obi-Wan Kenobi. There’s one “frenemy” relationship Obi-Wan had during the Clone Wars that I would love to see more of, however. Tales of the Underworld only makes me want it more.

Obi-Wan & Asajj Ventress Were Always The Best Enemies

As much as I loved learning about Obi-Wan’s short-lived romance with the Mandalorian Duchess Satine Kryze in The Clone Wars, there was something so undeniably enjoyable about his enemies-to-reluctant-temporary-allies dynamic with former Sith assassin Asajj Ventress. Of course, when they first met, their division was clear. Asajj worked for Count Dooku, had a hand in trapping and killing numerous Jedi, and utilized the dark side of the Force.

Once Dooku betrayed Ventress, however, she became something else entirely, finally free to chart her own course in life. Eventually, Asajj and Obi-Wan even had a common goal: kill Count Dooku. Their dynamic has always been flirty, and their bickering banter is top-tier. Obi-Wan even its that he finds her alluring, and she consistently insinuates the same.

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  Obi-Wan Kenobi

  Created By

  George Lucas

  Cast

  Ewan McGregor

  First Appearance

  Star Wars: Episode IV - A New Hope

  Alias

  Ben, Rako Hardeen

  Alliance

  Jedi

  Race

  Human

  The Padawan of Qui-Gon Jinn, Obi-Wan Kenobi became a Jedi Knight after his master's death. Obi-Wan trained Anakin Skywalker as a Jedi, with his own apprentice knighted after the Battle of Geonosis. The Jedi Master became a key player in the Jedi during the Clone Wars, and was heartbroken when Anakin turned to the dark side; Obi-Wan critically wounded Anakin before taking to the shadows, watching over the young Luke and Leia for years. He sacrificed himself for his two charges, becoming a Force Ghost and continuing to mentor them.

  Franchise

  Star Wars

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  Asajj Ventress

  Created By

  George Lucas, Genndy Tartakovsky

  Cast

  Nika Futterman, Grey DeLisle

  First Appearance

  Star Wars: Clone Wars (2003)

  Alias

  The Bald Banshee

  Alliance

  Sith, Bounty Hunters

  Race

  Dathomiri

  Hailing from the Nightsisters of Dathomir, Asajj Ventress became Count Dooku's apprentice during the Clone Wars. Betrayed by her master, she sought revenge - even forming a surprising alliance with Jedi Master Quinlan Vos at one point. Asajj has reinvented herself as a bounty hunter, and survived into the Dark Times of the Empire's reign.

  Franchise

  Star Wars

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This all happened when they were genuine enemies. Now, however, Asajj has seemingly turned her life around, having even realigned herself with the light side of the Force. We saw a glimpse of this new version of Star Wars: The Bad Batch and will see more of it in Tales of the Underworld. So, what might Obi-Wan think of her now? I want to know, but is there a chance we’ll ever see them together again?

We Now Know Asajj Ventress Even Helped Jedi During The Dark Times

There is one possible connection between Obi-Wan and Asajj Ventress during the Dark Times. The trailer for Tales of the Underworld confirms that Asajj was a part of the Hidden Path, a secret underground network that helped smuggle surviving Jedi and others fleeing from the Empire’s wrath to safety. This concept was first introduced in Obi-Wan Kenobi, and later expanded upon in the canon game Star Wars Jedi: Survivor.

Even more interesting, however, is that we know Ventress’ former lover, the Jedi Quinlan Vos, is also part of the Hidden Path, as Obi-Wan glimpsed his name carved into a wall when he and Leia were both taken in by the Path and its . Vos and Ventress’ love story is complex and tragic, but Obi-Wan played a role in bringing them together. The Jedi Council ordered Quinlan Vos to execute Count Dooku, and Obi-Wan suggested Ventress could be of use.

Learn more about Vos, Ventress, and the Jedi's plot to kill Count Dooku by reading Star Wars: Dark Disciple by Christie Golden.

Their dynamic is worth exploring further. So, if we know that Asajj helped the Jedi flee the Empire during the Dark Times, and we know that Obi-Wan is aware of the Hidden Path, what’s stopping Star Wars from bringing these two characters together again? No matter how much we may want it, canon might just be getting in the way.

I Wish We Could Have A Ventress & Obi-Wan Reunion (But It Just Wouldn't Work)

I will probably never stop wanting a reunion between Asajj Ventress and Obi-Wan Kenobi, but unfortunately, it just won’t work. Even though the Hidden Path feels like an easy way to bring them together, it’s not. After the events of Obi-Wan Kenobi, Obi-Wan returned to Tatooine, and as far as we know, he never left again until an older Princess Leia called for help. The next time we see Obi-Wan in canon again is in Star Wars Rebels when Maul and Ezra Bridger come to find him. That story takes place just before A New Hope.

Despite Star Wars’ penchant for dragging characters over to Tatooine – sometimes unnecessarily – there’s no real reason for Asajj Ventress to venture to that distant planet.

Despite Star Wars’ penchant for dragging characters over to Tatooine – sometimes unnecessarily – there’s no real reason for Asajj Ventress to venture to that distant desert planet and even less chance of her running into Obi-Wan while there. It would feel incredibly forced. Asajj has enough on her plate if she’s part of the Hidden Path, and Obi-Wan has no resources to help her. I’d love for Obi-Wan Kenobi to meet the person that Asajj Ventress has become since the Clone Wars, but it’s unlikely to happen in Star Wars: Tales of the Underworld, if ever.

Star Wars: Tales of the Underworld premieres May 4 on Disney+.