Teary McCrybaby Face

I finished The Walking Dead season 1 game not too long ago :D, I didn't cry at the end though it was a great ending but its hard to get me emotional in games xD What you should play next? Dark souls it will leave you crying for a whole other reason :D

Play To The Moon, then come back and tell us about crying :P

Dragon Age! Also Mass Effect to some extent, I suppose.

if you want to keep on crying, I suggest you watch Grave of the Fireflies

I went ahead and played (and finished) Gone Home as well. That didn't make me cry, yet I was compelled by it's narrative and atmosphere. I can see it being quite a polarising and perhaps divisive game though. I found it resonated quite deeply with me, being that I grew up and went through secondary school around the time that the game is set and felt like an outsider as well (although not to give away any spoilers, not in the exact same way as in the game). I'd also recommend this game to people who want a really different gaming experience (there's no combat, or even any other character interaction) and are fairly open-minded to the prospect of a narrative-based experience rather than a traditional "gaming" experience..

Have you tried Thirty Flights of Loving ?

BIT.TRIP presents... Runner2: Future Legend of Rhythm Alien is a pretty upbeat game I think. It doesn't have much of a story and is probably a game you can/should play in between, but I have no idea what drug the developers were on exactly. So there is that.

EDIT: ... I was (way) more emotional when the ending of The Walking Dead S1 rolled around, but not so much when I played Brothers: A Tale of Two Sons. I liked both games for what they are, but I probably had a hard time connecting with the brothers for some reason. I also kind of expected the end to be the way it was. The moment that touched me the most was probably when the controls changed in the end, to say it in a mostly spoiler-free way.

I was watching Cry play The Crooked Man. His last 2 videos had me crying. His voice and the meaning of the game made me bawl. Same as Season 1 & 2 of TellTales' Walking dead. I love games that get me attached emotionally, I just hate that it makes me cry (I'm just an emotional type of person).