All's well in moderation, I hope it doesn't get to the point where people are getting annoyed by it. Had something like this happen with Dating my Daughter during the jacuzzi day, I just hated it so much that I put it aside for 2 months x'D.
As for John I'd say you don't have to love him, but he's a cool guy and a good friend if you let him and respects the boundaries with Dana, so at least give him that
And just to be clear on the Jessica route: Chris will be double-teamed by both Dana and Jessica at the same time. Massive black strap-on'ing intensifies.