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I don't really know. :?
Considering I like being alone, it's hard to think of that as a negative thing. I'll have to think about that and edit this later.
Loneliest feeling...standing in the autum rain. Waiting for someone to arrive but they dont. And so you catch a cold/fewer etc. And you have to stay inside for a week. :D This would be it for me. (I hate being sick)
Silence. I live alone so I have to have some kind of noise on while I'm home or the silence really bums me out. It's not so much the actual silence as it is the thought of knowing that nobody else can break it because there is nobody else.
Waking up in the morning a month removed from a zombie apocalypse with only a pistol in hand with 2 clips, and everyone you loved and cared for either dead or a flesh eater.
A day or more without access to the internet. Honestly, my social life doesn't exist outside of it, so I'll definitely be feeling lonely if I have to go without the internet.
I'd say the loneliest feeling in the world would be silence for me. I mean, it's an incredibly powerful thing if you think about it. I just can't imagine what would make me feel lonelier than pure silence.
I never have a problem with loneliness, honestly. Growing up as an only child with no cousins the same age as you kind of drills that out of you :p
But, the loneliest feeling I've ever had was the first time my boyfriend stayed with me for a week (LDR) and when we drove him to the airport so he could go home. The drive back was miserable but when I got home and went to my room, it was probably the emptiest feeling I've had, at least recently.