I think at this point the first object is nailing down a CMS to start with, I'm leaning towards Dolphin but I have never used anything other than Joomla/Xoops to date.
Monetizing thoughts: Premium memberships, Adsense, Dating affiliates, Clickbank e-books (tons of them on breakups attractions regaining lost loves etc), Itunes/amazon sales of breakup songs self/help books. Other ideas?
Or maybe you can build a website about breakups between hollywood stars... Something that end up nasty like britney (leave britney alone.. LOL )
Or a section to that effect yes, good idea. I'm excited about the responses so far DP, can't believe I sat on this for nearly 3 years!
If I went with a premium membership section it would probably be a borderline dating site. Just an idea anyways.
You could have a section where people can make confessions. Oh lala! Sounds evil. "I cheated on Kyle last night.." "Mmmm...sorry Katie but Susan was better!"