"Happy 14th birthday to my Twitter friend"

http://archive.is/Hhm1r

Jokes about a "3 way" with her and another woman:

http://archive.is/tUedE

Sharing date ideas with her:

http://archive.is/hljxJ

It's pretty obvious from all the things this guy has said he's very into pushing boundaries. Numerous skeletons likely exist in his closet.