It was originally used to describe when someone tried to produce something that was circular, but failed (like an aircraft failing to perform a perfect loop or a glassblower failing to blow a perfect globe).

The term can be applied to any endeavor or plan that started out well but began to fail and lose its shape. (i.e., “When the first scabs crossed the picket line, the workers’ strike went all pear shaped.”)

I’ve seen this phrase many times, but never could figure out what it means. Help, anyone?

http://i80.photobucket.com/albums/j167/Lord_Paradise/Transmetropolitan_SpiderJerusalem.jpg

Your mom would have been like, “Lookin good, Brad! I’ve got several attractive women on the phone, and they want to come over to see your amazingly cool 3D glasses! Then I’ll leave.”

Unfortunately, your mom is sort of an unnecessary middleman in that situation, and might not be so agreeable. But you’d still look awesome.