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If he liked Robin Hobb would he like..?

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digopheliadug:
Possibly Lynn Flewelling?  I've only recommended that in the opposite direction (people who like Lynn should read Robin), because Robin Hobb books are like Lynn Flewelling books but better.  Still, if he was really into the Robin Hobb, Lynn Flewelling is really similar (and gets better as she goes along).

WrathandRuin:
Brent Weeks' Night Angel trilogy was very good; Kristen Britain is also very good, and recently released the third book of a story she started several years ago, so she shouldn't be hard to find.
I haven't read Lynn Flewelling (although I'm going to, now) but I second all of the previous recommendations.
I also recommend Neil Gaiman's American Gods as a good starting point on him, then Good Omens to get him into Pratchett (it worked for me, but in the opposite direction, Pratchett, then Gaiman).

Jackie Blue:
Ehhh.

I like Robin Hobb a lot.  I absolutely loathe Robert Jordan and can't believe I wasted so many hours reading his misogynistic drivel.  Robin Hobb is, in fact, the only "fantasy" author I can think of that I genuinely like these days, unless you count Michael Swanwick.  If he liked Hobb for the weirdness and non-traditional fantasy writing she has going, then definitely throw him The Iron Dragon's Daughter and its sequel, and Stations of the Tide and Jack Faust too.

I can't imagine anyone who likes reading seriously disliking Pratchett, so I have no idea why you're apprehensive about getting him to read any.  It's funny and poignant and completely without pretension; what's NOT to like about Pratchett?  The question really is, is he prepared to get into an author where he'll end up wanting/needing to read 40+ novels?

Surgoshan:
Pratchett's an easy read, but be aware that the early discworld novels are significantly different from the later.  The early novels are dark parodies.  The later novels are much more philosophical and yet, almost paradoxically, lighter in tone.

Jimmy the Squid:
Fiona Mackintosh is pretty good as well. I've only read one of her books but I enjoyed it immensely and have been looking to buy more, but alas, I have no money for buy books.

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