Searching for an old graphic adventure game
 

I realize that this is a long shot, but I'm looking for an old(late 80s or early 90s) graphical adventure game that I used to own and have forgotten the title of. I believe the title had "shadow" in it, but I might be misremembering. I've been trying to look up and recollect all the old adventure games I played(or watched my mom play) when I was a kid, and this is one of the first ones I remember.

I believe it was part of a series of three games, or at least a planned series. It came on either a 5 1/4 or a 3 1/2 floppy, I think it was a 3 1/2 but my memory of it is a bit fuzzy. I remember there was an easy mode and a hard mode. In the opening scene, you were in an alley and you could find a few items, one of them was a pair of underwear. In the next scene, you could walk into a store/bar, and there was a door at the top of the stairs that you could talk to a man inside. Then you could explore a city at night. In another scene, you were in a shack and you placed something in a beam of light to open a portal to a someplace outside(a different world, I think).

I found this forum via a google search, and it looked like older games were discussed here, so I thought someone might happen to remember the game I'm thinking of. Any help on this would be appreciated.

It seems rather unlikely, but could it be Monkey Island 2? Some elements you mentioned remind me of it.

Sounds very much like Dare to Dream by Epic MegaGames. I was actually thinking about that game a while ago, but for the life of me I couldn't remember the title - today it popped up the moment I read your description. The mind works in mysterious ways.

Interestingly, Dare to Dream was developed almost single-handedly by the then 17 year old Cliff Bleszinski who later went on to game designer stardom with the Unreal and Gears of War franchises.

That's an interesting bit of information GarageGothic. I didn't know Cliff Bleszinski made an adventure game.