There’s certainly nothing wrong with personal happiness, only when it becomes a singular focus. He would wish the same for her and Ezra both. And yet there’s this hesitation on his part. Which is only emphasized by the last thing Ezra says.
The Jedi Master takes an uneasy breath. It’s clear that he isn’t entirely comfortable with all of this. For a multitude of reasons.
“No, you’re not a Padawan anymore,” he says quietly. A thought that pained him a little as their time together as master and apprentice had been so… brief. “Neither was Anakin,” he continued, letting that hang for a moment.
“I know what it’s like to have these feelings, and to get swept up in them. I told Anakin much the same once. Unlike you, he wasn’t inclined to listen and was much deeper into it than I realized.”
There is regret in his tone. Wishing he had tried harder, had done something sooner to keep that disaster from happening. He knew it was useless to think that way, but letting it go was easier said than done.
“I know you’re not him, and I do trust you.” A pause. “There is no order here or back home anymore. Despite that, we had our rules for a reason. I find it difficult to think that such a relationship, and remaining a Jedi, would be compatible.”
“He was fortunate then,” Obi-Wan says quietly. He doesn’t know the circumstances or that he would have agreed with Kanan’s decisions, but he was glad for the outcome in Ezra.
It was something he knew he would never have. Whether it be circumstance such as hiding in solitude on Tatooine for 20 years, or his own beliefs and fears holding him back. It was simply how it would be. However…
“No matter what I might think or feel on it though, I won’t hold you back.”
"He was." Ezra does believe that. " And thank you," the younger man replies, solemnly.
"I didn't want it to be...a secret. Or something you didn't feel like you could talk to me about, if you think you see something, um. Really concerning."
That gets a little chuckle out of Obi-Wan. “Oh it wasn’t a secret.” Obi-Wan had known since Ezra introduced him to Sansa. Despite the time gap he remembers that well.
“But don’t worry, if I do see something concerning, I will be sure to tell you.”
Ezra makes a put upon face and gently grumbles, "You know what I mean." He's pretty sure Padmé and Anakin weren't remotely as much a secret as they thought, but the 'secret' certainly caused problems anyway, didn't it?
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The Jedi Master takes an uneasy breath. It’s clear that he isn’t entirely comfortable with all of this. For a multitude of reasons.
“No, you’re not a Padawan anymore,” he says quietly. A thought that pained him a little as their time together as master and apprentice had been so… brief. “Neither was Anakin,” he continued, letting that hang for a moment.
“I know what it’s like to have these feelings, and to get swept up in them. I told Anakin much the same once. Unlike you, he wasn’t inclined to listen and was much deeper into it than I realized.”
There is regret in his tone. Wishing he had tried harder, had done something sooner to keep that disaster from happening. He knew it was useless to think that way, but letting it go was easier said than done.
“I know you’re not him, and I do trust you.” A pause. “There is no order here or back home anymore. Despite that, we had our rules for a reason. I find it difficult to think that such a relationship, and remaining a Jedi, would be compatible.”
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"I do get that. At least, I think I do. But my experiences are-" Different.
"Kanan- Hera helped Kanan want to be a Jedi again. To look beyond just...getting by and keeping his head down. Take the risks. Take a risk on me."
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It was something he knew he would never have. Whether it be circumstance such as hiding in solitude on Tatooine for 20 years, or his own beliefs and fears holding him back. It was simply how it would be. However…
“No matter what I might think or feel on it though, I won’t hold you back.”
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"I didn't want it to be...a secret. Or something you didn't feel like you could talk to me about, if you think you see something, um. Really concerning."
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“But don’t worry, if I do see something concerning, I will be sure to tell you.”
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More firmly he adds, "Good."