Transcribing US Weekly

For my cut-up experience I brought in a bunch of my roommates' old US Weekly magazines. As you can imagine, there are lots of trashy articles I could have pieced together. Here is what it looks like:
I pictured this being read with the left column first, then the right rather than straight across. In that case, here is the transition between articles in the left column: "Shes smart and sharp-witted, and has a lot less high fronted with the image of an (unimpressive) penis poking out of smiley face-covered boxer shorts." Haha, can you tell where the transition is?

Here is the one in the right hand column: "The gold bauble, which TMZ.com claims to be worth dochine with John Mayer August 14 for an evening of flirting and sipping wine, they settled into a cozy booth."

Personally, I don't understand how anyone can cut and transcribe and have it make sense-this was hard!