Despite playing for about 5 years now, I've never changed the strings on any of my guitars because I was too lazy to and it seemed tedious.

Lo and behold, my first time re-stringing my though body guitar and the little metal piece the string is fed through on the front popped out of the damn wood when I removed the old string. Tried putting it back, but it won't stay in. Is this normal, or is it broken? If I stick it back in and put the new sting on, is going to just pop out of there or what?
Get some super glue, put it on the sides of the little thingy, called a ferrule by the way, and stick it in the hole. Hold it there for a few minutes, and it'll stay put.

My things:
Bowes SLx7
Washburn WG587
Washburn X40Pro
Washburn X50
Washburn HM24
Washburn WR150
Laguna LE200s
Arietta Acoustic
First Act
Valveking 112
VHT Deliverance

Set it with a wood-to-metal adhesive and stick it back in. Whatever you do, DON'T try to restring without it. A friend of mine (bit of a n00b) did that and his string that was missing the ferrule cut a groove into the body of the guitar. Those little suckers are important.
1989 Kramer Showster
Rogue RADH Acoustic
Fender CD-60 Acoustic
Washburn XB-100 4 string
Peavey Millenium AC BXP
Fender Rumble 150
Crate BV60H Head
Crate BV412 Cab
Vox AD15VT