A (slightly less) non-comprehensive list of Obi Wan Kenobi’s currently open offers of marriage*:
Waxer and Boil. It was a desperate situation. The General was desperately injured, and was trying to run from the med droid instead of being treated. Both had the same idea at the same time and got on one knee to distract him. He was discomfited enough to be ushered back to bed.
Cody**. He was once again picking up Obi Wan’s lightsaber, already on one knee. “General, we need to stop meeting like this. Let’s just make it official.”
Anakin Skywalker. He will not be outdone by Cody. Obi Wan promptly checks him into medbay.
Padmé Amidala. Anakin goes to complain at her, “you accepted my proposal, I don’t know what I’m doing wrong here!!!” She reminds him that she essentially kidnapped him from Vokara Che and married him after Obi Wan told her not to. Anakin, missing the point, counters “so Obi Wan proposed to you on my behalf is what you’re saying!! So clearly you have to go there and tell him not to marry me!” And so Padme goes, but something gets a little lost in translation, and Obi Wan is gentle. “Padmé, I think Ahhnakin might be offended if I accept your hand.”
Quinlan Vos. Quinlan proposes frequently and with vigor. It’s different every time, but memorable is the time he proposed to Obi Wan right in front of Master Windu. He got archive duty for the next two months. His request to Canto Bight’s express officiant was never cancelled and remains open to this day. Obi Wan’s amusement with the situation got him assigned to crèche duty.
Taria Damsin. She spots him laughing while drowning under a pile of snuggly younglings and proposes on the spot. Mace Windu assigns him to solitary meditation.
Bail (and Breha) Organa. Bail catches Obi Wan performing his forms (in Bail’s defense, Obi Wan was just wearing his leggings and nothing else). Bail immediately comms Breha like “honey I found us a hot jedi sidepiece, I’m proposing!!”
*still does not include any offers Obi Wan has already (very politely) declined
*still a very non-comprehensive list, this cannot be emphasized enough
**technically this offer of marriage is not open… Obi-Wan recovered his sass and waved Cody off with a “sure Commander, let’s.” It is the only proposal he ever accepted.