Ryu Ga Gotoku Studio's director, Masayoshi Yokoyama, has revealed that, despite his conversation with Ichiban in a recent clip for Like A Dragon: Infinite Wealth, Kiryu hasn't actually proposed to anyone before, which means he might still be a virgin.
For the longest time, one of the main questions that Yakuza fans have had about the series is whether or not its lead, Kazuma Kiryu, was still a virgin. We've seen him have presumably intimate relationships, like with Kaoru Sayama in Kiwami 2, but it was never clear if he'd gone all the way, something that seemed even less likely when series producer Masayoshi Yokoyama said he personally believed Kiyu was still a virgin because he was holding onto his pure love for Yumi Sawamura.
That, combined with Kiryu's gentle nature when he isn't beating the snot out of people, made it seem pretty definitive that he was a virgin. Then, RGG Studios shared a clip of Like A Dragon: Infinite Wealth that showed him and Ichiban having a heart-to-heart. In that conversation, Ichiban reveals he was rejected after he proposed to Saeko, which causes Kiryu to not only suggest that he's proposed in the past too, but that he's also "been around a few times", suggesting he wasn't a virgin.
This absolutely blew everyone's mind when it was so casually dropped out of nowhere, but it seems that it was a bit of a red herring. As pointed out by GamesRadar+, RGG Studios' director Masayoshi Yokoyama explained in a recent interview with Gamer Braves that the comment made by Kiryu wasn't meant to be taken seriously and was more of a joke than anything else, which means that he likely hasn't actually proposed before.
Yokoyama said, "With regards to the answer made by Kiryu and the mentioning of the proposal, it was actually very lighthearted. There wasn’t much depth to that answer. He just kind of wanted to go with the flow of the conversation and say, 'Hey, you know what, I proposed before.' without thinking much into it. So there won’t be any kind of further talking to the actual proposal in the background of that conversation because it was mainly just out of fun".
It's a little bit weird for Kiryu to be so casual about such a big thing, especially when Ichi clearly takes it to heart and believes him, but if it's true that Kiryu is just joking, it stands to reason that his comment about how he's "been around a few times" is likely just a weird joke from him too. At least he seems to have a pretty good relationship with Ichi, even if it is built on a tower of LIES.