Perhaps it is Jake's attitude and boldness.
I think Eric could do well to take a hint from him. Not that Jake's any kind of role model, but Eric is almost timid around Calleigh at times. He is bold, he has all those characteristics, (in a good way, unlike Jake's arrogant way) he just doesn't exhibit them around Calleigh when things get personal. With everything else, like work, Eric knows exactly how to handle Calleigh, to push her just the right amount, to call her out when necessary. Something gets personal, he won't push it at all, probably through fear he'll push it too far. He wouldn't, of course. Jake would. But, as mushy as it may sound, Eric is totally perfect compliment to Calleigh. He knows how to handle her in every other situation, so why not this?
Personally, I think he needs to give Calleigh a bit of a nudge. To confront her, but not in an angry, overly emotional kind of way. I kind of like to see him just calmly lay it all out for her, and then leave the ball firmly in her court. She's gotta make the move.