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Howard Wise/JPI (2), Aaron Montgomery/JPI, Matthew Olsen

Is history about to repeat itself?

The Wednesday, Sept. 22, episode of The Young and the Restless finds Jack accepting the riskiest of propositions: He reflects on his past decisions and ponders how they might be affecting his present and future.

Now on one hand, that could be swell for the tycoon. It’s never too late to learn from one’s mistakes, right? On the other, it could be an incredibly painful and frustrating endeavor. What if Jack discovers where he went wrong… and doesn’t see a way to make it right?

More: Redemption for former Young & Restless baddie?

Considering how heavily Phyllis has been weighing on Jack’s mind lately, we have to assume that their failed attempts at marriage will come up in his musings. If he realizes now that he should never have let her go, what will he do about it? Would he actually throw down the gauntlet and vie with former stepson Nick to win her back?

Jack, Phyllis engaged Y&R

Given how much Nick has suddenly been analyzing his and Phyllis’ relationship, Jack might not even have much of a fight on his hands. As tempestuous a romance as he and Summer’s mom have, is it the same kind of true love that he once shared with first wife Sharon? If it isn’t, is that OK? Is that enough or even better?

Should Nick come to the conclusion that in the end, he and Phyllis aren’t meant for one another, the path would be cleared for Jack to come rushing in to try to sweep her off her feet and into his arms. While we wait to see what new light his trip through the past sheds on his future, stop off at the photo gallery below for a history lesson in the ladies’ man’s many, many loves.