Need some help tracking down a movie!

[Data Holmes]

Ok, so this has been a mission for me going on like 15 years now.

I'm looking for a movie I saw once as a kid. It was on pay tv when I saw it in the late 80's to early 90's. It was about this kid, a homeless/wrong side of the tracks kid who, through lies and confidence techniques, works his way into a wealthy community, charming the women, young and old, to get money. But when he falls in love with one of the girls in this community he hits a crossroads and must choose the con or her. He ends up choosing the girl, but either he is exposed before he can confess, or he admits it publicly at a gathering and the community is shocked.

I think part of the con may have involved getting/being engaged to one of the rich girls when the one he loved wasn't...

In the end he ends up with the girl, and I think has to work a real job to pay back the money he conned out of some people.

I used to think the kid was played by patrick Dempsey, but none of his early movies match up, however the kid/guy who played the lead may have looked like young PD and that's why I was thinking that.

Anyone have any ideas, any help would be much appreciated after trying to figure this out for so long.

 

[Admiral Shran]

Hmmm... it sounds kind of like the 1989 movie Worth Winning with Mark Harmon, Madeleine Stowe and Lesley Ann Warren.

I could be wrong though.

 

[Data Holmes]

Hmmm... it sounds kind of like the 1989 movie Worth Winning with Mark Harmon, Madeleine Stowe and Lesley Ann Warren.

I could be wrong though.

Looks like an interesting movie, but it isn't it. The lead was more of a late teen, early twenty range character just out of high school early college age.

I'll be checking out this one though as I'm a big Mark Harmon fan. Thanks for trying to help out.