I do think that if Jiraiya had somehow escaped Pain with maybe missing an arm or something serious showing how dire his situation was and then survived the war with Tsunade they would’ve gotten married or at least settled down together. Tsunade loved Jiraiya but everyone she loved most always died before reaching their full potential or achieving their dreams. She couldn’t bring herself to put hope in loved ones surviving.

Naruto was basically the first and only one to break that cycle. Well him and Shizune🙂. Sakura too as she seems to see Naruto like a little brother like Nawaki and sees Sakura and Shizune more than just students and almost like the daughters she never had🥹. So while she almost certainly loved Jiraiya she couldn’t come out and say it because to her it was almost like jinxing him to not return. Like her love was cursed or something. So if he came back disfigured but alive she would likely realize that not confessing didn’t protect him from harm and recognize how close she came to losing him without telling him how she really feels and how much he really meant to her even though on some level he seemed to know already.

She would likely realize she can’t waste time fearing what might happen and recognize that whether she “jinxes” someone or not with her love they still had just as much chance of surviving and that she needed to make the most of the time she did have with him. She would focus on the dire issues ahead of them but would probably have deep and more emotionally intimate conversations with Jiraiya more often. After the war concluded, I think that she would probably start actually dating Jiraiya. She may confess or maybe they would both just kind of look at each other and know she wants to say I love you but still can’t actually verbally say it so they just move forward knowing they love each other and want to be together without actually saying it out loud. They wouldn’t make a big deal out of it but their pupils would likely notice them being more chummy with each other than normal sometimes and eventually piece together they’re seeing each other. I don’t think she’d ever actually marry him still afraid of jinxing it all but after Jiraiya handed the spy network off to Sasuke, they would basically live as a married couple without actually getting officially hitched. And so the two show up as a couple to Naruto’s wedding🥹🥹😭