I really like Sophie Blackall's illustrations of missed connections ads from Craiglist and other sites. The style reminds me a bit of Maira Kalman.
If this were on Tumblr, she'd already have a book deal.
Update: About that book thing:
Ms. Blackall's whimsical drawings have also caught the attention of publishers: She says she's currently negotiating a deal to create a book of her illustrations, which would likely land on shelves sometime in the next year to 18 months.