I mentioned Rav Leib Gurwicz earlier. A bochur who merited being the ‘hoiz bochur’, told me his best moment was when he came to the yeshiva to tell everyone that the Rosh yeshiva had just got engaged. He remarried to Rebbetzin Isbee from Detroit.
Also, the Chofetz Chaim famously remarried and had a child, Rebbetzin Zaks at age 70.