Oh man. This is like the ultimate canon vs. canon (but not really). I'm kind of waffling on it now, because while I don't want to be that guy that says, "Well it has to be that way", it is part of Jack's character (as much as I would be happy if it wasn't). I'm not sure if they're all that compatible for an event, because either way it ends up contrary to their characters. After all, Jack is written as being irresistible to women (except those who've had enough time to know him) in some wish fulfillment writing of some very male authors. The irony, being, that I don't even RP sex.

So yeah, I think it might be a little too awkward to play out. It might be better for their CR to just keep doing what we already have going on (which will be pretty much the same as you described) and preserve their CR.