I'm one of those guys who is looking for the feels but is never prepared for it. However, we have to admit these feelings make living and anime or anything just that much better.
Warning! There are spoilers ahead so as soon as you see something you haven't watched but are going to, just RUN! RUN THE HECK AWAY!
Toy Story 3 - Incinerator Scene
I ended up watching Toy Story 3 because of my little sister but man....before watching it, some people said be careful and even at the cinema some people were coming out with red eyes, and I wasn't prepared for this.... I never a story about toys could make me feel like this AT ALL. For those who have watched it knows what I mean. I could also go for when Andy leaves for college.
Pokemon - Ash's Butterfree
This has to be my first taste of the "Right in the feels". Even though I was a kid back then, I just couldn't stop crying. Damn it, I can't even stop crying right now as an adult.... Next slide before I dehydrate.
Angel Beats - Kanade Dissapears
If we're talking about the feels, Angel Beats has to be here. To be fair, I could've put any scene from Angel Beats and the feels would come out automatically. However, this scene marked the ending for the anime and it's different from the other people disappearing. Not only that, the soundtrack....that song man....it hits you so hard you'll never ever forget this scene. No wonder no one has succeeded in the "No Cry Challenge" for this scene.
Charlotte - Ayumi's Death
I developed a sister complex for Ayumi in the first few episodes and I'm sure a lot of you can agree and see why I'm like this. I got the feels but I got so angry thinking to myself "Don't you dare Charlotte...." but it ended up happening anyways. I did finish the anime even though I was so mad at it, also because I wanted to see that this was all a dream.
Death Note - L's Death
How's this fair... Saddest moments for any Death Note fan but also one of the creepiest to some extent. It's like they don't even warn you for it and surprise PUNCH in the face... However, I do admit it gave Death Note a new sense of direction and we were always eager to see what was to come.