For a while there we had WebForms, which was used much like WinForms, but generated the controls in HTML, CSS, and JS. That technology was very much not fun to work with, for the few projects I used it on. I built a full website using Sitecore CMS back when it was fully WebForms, and having come from PHP for web development, it was painful. It tried to paste over the way the web worked, which would have been fine had I never touched web development. Once ASP.NET MVC was introduced, things got much better for .NET developers.

I actually learned VB6 alongside Java in school, so migrating to VB.NET was fairly easy for me, but once I saw C# I jumped ship immediately. I turned my existing VB.NET code into DLL files and called them from C# from that point forward.