Here's a funny series of geek art created by artist Chris Gerringer called I Know That Feel, Bro. The art includes a collection of classic geek pop culture characters that are looking for a shoulder to cry on. As you will see each character pairing has a little something in common.
Source: Geek Art (http://www.geek-art.net/chris-gerringer-i-know-that-feel-bro-series/)