There's been a fun thread running over at TalkBass about "the one that got away"... I have a couple, and I bet you guys do too.
Actually, the one that really hurt the most (I've mentioned here before) was a Martin D-16H. (H was for 'herringbone') C.F. Martin & Co. made a special run of them in 1992 with some custom features, and I got the very first one that came into Roanoke. It had a beautiful Engleman spruce top, and lightly quilted mahogany sides and back, and that awesome tortoise binding they hadn't used for years. It had herringbone purfling back strip and rosette, and gorgeously scalloped braces under that white-gold top. I was in love at first strum. The guy that ran (and still runs) the local music store let me pay it off on an extended layaway for six months, and would occasionally even let me take it to a gig or fiddler's convention while still paying on it. It was plain-and-simple, made just for me.
Anyway, long story short, hard times came, and I had to sell it to pay bills and subsequently a divorce lawyer.

There was no extended layaway plan for that, so I cried every night for six months...

over the guitar more than anything else. It's been nearly 20 years ago now, and I swear if I ever see #518842 again, I would buy it back in a heartbeat, even if it's a box of splinters and I have to pay full-new price.
Here we were back in the glory days... note that someone has been scissored out of the Road Warrior pic... yeah - she was the reason it got sold. The other picture was taken backstage at the Roanoke Civic Center. I'm 99.9% sure this picture actually captured the conversation where I was hired by Acoustic Endeavors to be the new bass player, a relationship that would finally put me on the road, thus beginning my professional music career/crash diet. If I'm right, that would have been early Spring of 1994. (dig that Dale Earnhardt 'stache and Indiana Jones hat!)

So... which one did you never get over? Bass, guitar, or whatever?