Quote ksupergirl: I think Jack and Jill would be a great match. Jack RESPECTS Jill both as a woman and as smart business executive. Jill is intelligent, a business savy executive just like Phyllis, and she's tough like Phyllis. Jack likes smart, strong women and that's exactly what Jill is. Jill is Jack' equal in every way just like Phyllis was.
Here's another reason for Jack to like Jill. She's RICH, very rich.
Jack's last two romances have been a disaster with the viewers. This is a romance that is age appropriate and one the viewers would approve of.
And Jack could possibly take control of Chanceler Industries some day!!! That alone should be enough to entice him!!!!! :-) :-)