So here is the thing, I have played JRPGs for a really long time, I'm totally passionate about them and I totally love them. However, recently, thanks to a few interesting articles, I've wanted to get into WRPGs. I was simply wondering where is good place to start? I want something challenging but not to horrifically tough, and something with an interesting story and engaging characters.

note: I've played like Skyrim, Oblivion, ME2, Fallout 3, and New Vegas.

I will just say this to you, the RPGs here are FAR different then those RPGs you play for 1 reason there is almost no hand-holding elements like waypoints, you have to read.

As for my recommendation: Fallout 1

Edit: here is more if you want a silghtly more easier experiance, Legend of Grimrock and Torchlight, they are a little easier.

Man would I like to see his first reaction to Fallout 1 after playing only Skyrim, Oblivion and Mass Efect. :)

My experiance with Mass Effect 1 was hard at first, the enemy AI are not programed like most shooters. They don't take cover they sometimes run up to me and shoot me anyway so the cover system in the game is kinda useless.

The Witcher

One of the few games that made me care about the characters.

You might start worrying about me here, but I don't think so. For the first western RPG, I would just go with the popular stuff: Mass Effect, Dragon Age, the usual. If he likes those, more experimentation would be in order. Ha, want some reading? Play Planescape: Torment. Will give you all the readin you can possibly handle :-P

It's actually funny you should mention The Witcher because I bought it on steam and was super excited to play it because I had heard all of these great things only to realize 'hey my computer is total shit.'

If you can enjoy action RPG gindfest you could always go with Diablo or one of few million of his clones. :)

'Western' RPGs is a really broad genre, larger than JRPGs from what I've seen. Here's some recommendations for the subgenres.

Action RPG: Torchlight, Legend of Grimrock

Party RPG: Balder's Gate 2 or Planescape Torment

Single PC RPG: Morrowind or Neverwinter Nights expansions (main campaign is generic).

People seem to like Silver (currently on sale), and I'm interested but haven't played it yet. Gothic is also highly rated, but odd, and the controls are apparently actually painful for some people.

Morrowind is somewhat similar to Oblivion in terms of controls, mechanics, etc. But it's got a vastly better story and more engaging characters. Also, with the ME Graphics Overhaul I think it looks better than Oblivion (Bethesda can't do faces to save their lives, IDK why). LInk for Overhaul: http://www.ornitocopter.net/mirrors-mirrors-mirrors/

Arcanum (available on GOG) is an example of how great western RPGs can be (it has flaws, but the awesome make them seem inconsequential).

Dragon Age is a good choice. Maybe Neverwinter Nights 1 and/or 2. Older BioWare games always felt to me more like JRPG's than most WRPG's.

I'm not really a fan of most "open world" RPG's (Elder Scrolls games and the like), as I prefer a more focused experience for the most part.

I was excited for The Witcher, but I HATED the controls.
I never really Diablo-esque style ARPG's, so I stopped playing them. I need an engaging story, even if it's ridiculous.

Sadly, since the 90s, most WRPGs have really weakened, focusing more on large open maps and non-linearity than trying to be an actual good game, and for the most part, this has only weakened the genre, save for a few rare exceptions. If you need modern/semi-modern Neverwinter Nights and its sequel are probably the best in terms of mechanics, though if you want story, Star Wars: Knights of the Old Republic II: The Sith Lords, The Witcher, or Deus Ex (avoid Invisible War at all costs) are the way to go.

However, if you're willing to try some older games, the first five Ultima and first six Might & Magic (not to be confused with the Heroes of Might and Magic spinoffs which, while excellent games, aren't really RPGs) games are awesome.

I don't think too many RPGs are open world and RPGs like Fallout are not linear, you can go to the final boss even at the beginning of the game (which imo is kinda silly)

Seems to me that most big name ones are nowadays... But maybe that's just because I think more of what I see discussed on other forums than anything else.