We'll see. [ He might or might not. It really depends on what stage of life he's on, so hmm, hmmm. ]

It's completely your fault for continuing to play truth-or-dare with people like me.

[ Hershel gets flustered at the smallest things and no, Jake got him a second base sweater for Christmas and Hershel is going to LOVE IT ]

You got a point there, but asking her out to coffee or whatever you do isn't going to kill you or her. It's casual enough.