How do you know it's not recognizing the key? As far as I know, there's no reason to press # at any point in either MM1 or MM2.

If it looks like the game is asking you to press #, it's probably asking you to press one of the number keys, most likely the one corresponding to the town whose inn you want to start in. If you just started a new game, you want to press 1 here.

MM2 works the same way.

(This is a very common question, so don't feel bad about asking it.)

The attached screenshot shows where it's asking for #. Thanks for the info though, pressing 1 did work. :D

Hello JoeMD!

I did not come across this issue myself, but on some occasions with both DOSBOX and Windows games it helped me to switch in Windows (on the Operating System end) the keyboard layout from one region to another. Especially Laptop and Notebook keyboard layouts vary a lot between regions and thus, may allow for accessing the necessary key (' # ' in your case) easier, on an entirely different key location without the need for a multiple key combination.

The older the game, often I had to change from my European regional keyboard layout to an American one. (The virtual on-screen keyboard helped me to learn about new key locations on my machine, since a number of keys and their function do differ.)

Maybe, you might try even a German keyboard layout, as well, for those can have the ' # '-key on a Laptop keyboard on the one next to the RETURN-key (on the lefthanded side directly above the right SHIFT key) without requiring any SHIFT-key combination).

I hope this might provide a workaround for your issue.

Kind regards,
foxgog

[Edit:]
Just to be sure, it's a long time ago that I had played M&M1, but you have created at least one character, already, right?
Because without any playable character in your party you won't be able to proceed in the very beginning of the game.