Tony's Lovers..

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Definitely not at any point before the A.J. and Meadow were grown up and out on their own. He seemed quite content with having a "goomar" & meaningless flings on the side, with Carmela at home to run a stable household. I'd say it was a possibility once the kids were out of the house though. When he was considering an affair with Adriana, he openly discussed with Dr. Melfi the idea of having children with her since she was still in her child bearing years, ironically of course since she was "damaged goods" in that regard. That right there shows that he was contemplating the possibility of replacing Carmela with a younger more fertile woman to start another family with.

I think Dr. Melfi hit this assessment of Tony right on the head. I forget when it was, but it was sometime before Tony and Carmela separated.

"Anthony, you would never leave your wife. She might leave you, but you would NEVER leave her."

Valentina was always my favorite of Tony's goomah's, but she had to many other things going on that she would never just give up to be the Italian wife that Tony would want. Plus we don't know how any of the girls would have felt about Tony banging other girls while with them. They all seemed to be naive enough in their own ways to think they were the only girl Tony was cheating on his wife with.