Writing this as a blog post to someone because it won't fit in a comment (over 1000 chars)
The “Test of Time” Award : Sid Meier's Pirates!
Yep, I'm ooooooold. :) The first version I played of this was the C64 version. But this game is good!
The “I'm Not Crying, There's Something In My Eye” Award : Actual Sunlight
DO NOT PLAY THIS WHEN DEPRESSED. PLEASE. It's not like a normal tearjerker thing, it's a full-on depression thing, but it has real emotional impact, enough that I wanted to nominate it beyond anything else I played (even though I actually played it on PS Vita rather than PC/Steam).
The “Just 5 More Minutes” Award : Chime Sharp
I was going to award this to Stardew Valley as I have accidentally played that one to sunrise without noticing before. Chime Sharp only makes me mysteriously lose around 4 hours every time I play it.
The “Whoooaaaaaaa, dude!” Award : Circa Infinity
You might have seen my little review earlier.
The “Villain Most In Need Of A Hug” Award : Steins;Gate
So much would have been different if only [certain persons] had more hugs!
The “Game Within A Game” Award : Stardew Valley
Great minds think alike. :) I really like the mini-games in Stardew Valley.
The “I Thought This Game Was Cool Before It Won An Award” Award : Black Closet
It might be the game I did more early recommending to other people than any other.
The “Best Use Of A Farm Animal” Award : Space Giraffe
The bonus rounds are full of seriously good mooing.
The “Best Yuri Game” Award : Kindred Spirits On The Roof.
The curator of the "Hella Yuri" steam group - who is Hanako of Hanako Games - made a call to all members to use the free vote on "Best Yuri Game" in an attempt to make Valve-sempai notice the yuri community, so I thought I'd pitch in. :)