I need someone capable of playing a smart, sexy, 40+ female in a private line. Basically, my guy and your character would have met when they were in high school. They were always close and great friends, but despite being a perfect match, they never tried to further it, both knowing it wasn't the right time for them. Now they just so happen to have met back up after losing touch years ago. He's still single, she's divorced (or vice versa), and they're so comfortable together it's like no time at all has gone by. I'd prefer playing Jeffrey Dean Morgan. Leave an AIM if you're interested.
Alternatively, I can go for his sweetheart having changed over time while her daughter grew into the girl he used to love. It's up to you!