Yeah, I have the same problem, with 0.38.2, even. It does that where it remains stuck at initializing, and never prompts for the password. To work around it, I have to delete the Jojatekok folder every so often that is stored under C:\Users\your_username\AppData\Local\ before opening up the GUI, then it will prompt for the password and load the wallet. Just deleting the config file doesn't always work for me, but deleting the entire folder does, for whatever reason.