Obi-Wan missed Satine so much. He often thought about her. He missed seeing her beautiful face. If she were still alive, he would've proposed to her. He often regretted not popping the question before she got killed. And just like Anakin, it would've had to be a secret.
If Obi-Wan and Satine had planned a wedding, Anakin and Padme would've been the only guests. R2D2 would've been the only other guest, but no one else. Not even Ahsoka. The wedding would've taken place on Mandalore. The wedding would've had to be secret-just like Anakin and Padme's wedding was. At the same time, it was a good thing this was also a thought for Obi-Wan and Satine both.
After Satine got pregnant, she and Obi-Wan wanted to get married after the baby was born. But with the miscarriage and her being killed by Maul, the whole thing was off. But Obi-Wan would never forget the time he saw Satine again. And he'd never forget the time he met their daughter Ivory. He regretted not proposing to Satine, but he kept thinking to himself that she wouldn't want him to regret something like that. She'd want him to know that they were blessed to have known each other. Even if it was something more.
Not a day had gone by that Obi-Wan didn't regret not saving Satine when she was killed by Maul. But he just kept thinking that she'd say that it couldn't be helped. Okay, he knew it couldn't be helped, but he still felt that tinge of regret. If Obi-Wan HAD proposed to Satine, she would've said yes. Even if it meant taking huge risks-just like Anakin and Padme. Whether attachments were allowed or not, Obi-Wan still loved Satine. She was different from the other girls Obi-Wan had loved. She was special.
When Maul sent Obi-Wan to his prison cell after Satine got killed, Obi-Wan just wanted to kill himself. This was dismissed after he thought of Satine would've thought. SHE would've thought it was crazy and unforgivable. She wanted him to stay in the world because of what he did. He was a Jedi. And he wasn't going to give up on her, Ivory, or himself. It meant the world to him when he saw both of his girls. Since then, he's had his pride go through the roof. And it couldn't have been any more empowering than that.