I gather a silent H is part of the answer, but I can’t get any further than that.
Neo’s Mom’s name is Mrs. ____
ANDERSON (and 'er son)
I thought you were changing the answer from 8 letters long to 3,2,3.
Sissy depicted young sleuth (5, 4)
Sissy depicted young sleuth (5, 4)
NANCY DREW
+++++
Cry when I fail (5)
WHINE (anagram)
Evil neighbor is a modern dude. (6)
Hint: “evil neighbor” refers to a character in a popular sitcom.
I’ve got the Seinfeld gif all cued up; I’m just trying to craft a good follow-up clue.
+++++
In giving a man a clever line, you can lock him up. (7)
In giving a man a clever line, you can lock him up. (7)
MANACLE (container)
+++++
M, A, I, and L. (7)
LETTERS (double definition)
Ruin the end of the Metro (5)
SPOIL (anagram of POLIS, which is the end of METRO, AND it means “ruin the end of”! Very elegant and efficient crypto!)
+++++
Deprived of the imaginary part of my social environment, I’m suddenly all about my gut. (5)
No one?
Okay, a hint: You only deprive me of one of the "i"s, not both of them.
Does “society” figure into the solution?
No, not really. But a word that means “social environment” will be modified and anagrammed.
I’ve been trying to think of synonyms for “social environment” that have the letter i, but I can’t think of any that can be morphed into the solution. Building, village, university, office, milieu, dwelling…
ILIUM (milieu minus e)?
No, but very close.
The ilium is a bone, btw, not part of the gut.
ILEUM part of the small intestine.
That seems to work.
I defer my clue to The Prof for getting it essentially correct (plus no time to think of a good clue 
)
Well, the ilium is part of the pelvic girdle, which encircles the gut, so to speak. Ah.
Thanks, Oly!
Little women go mad for basketball this season. (5)
MINIS is the best I can come up with.