Expert: Susan Dunn, Dating Coach - 1/8/2010

Question
Dear Susan,  
   Thank you for taking my question, a quick response would be appreciated, i have knots in my stomache. To make a long story short, i went to school with this very shy guy, he was 1 year behind me. I had a crush on him, but never acted on it, i was just as shy as he was...and nothing ever happened.
   Through the years, i found out he inherited millions from a stepfather, and moved across the country.  He's been there for 25 yrs. now, and never dates anybody. I am 46 yrs. old and he's 45. I know his uncle very well, he was my softball coach, i worked for him for 3 yrs., and he was also my landlord...we're just friends. He's a VERY generous person, and thru the yrs. he's taken many people on vacation with him. He asked me if i wanted to go see his daughter, and his nephew, who both live across the country. I did go with him, it was a wonderful vacation, but....
I think i have fallen for the nephew, the bad part is...he has inherited millions of dollars thru family. What's wrong with that?
Well that's not me, money is not what i'm looking for, and never has been. I had a crush on him before the money came along. The thing is...#1-he will think i want his money, #2-he's so incredibly shy, he hasn't dated anyone all these yrs., according to his uncle. I am so scared of being rejected. And he's clear across the country, too easy for him to say no. I am attracted to his personality, and always have been. How do i convince him that i'm not after his money? and how crazy i am about him? I have knots in my stomache, i have to do something soon, this cant be healthy for me. Please tell me what move to make? I'm desperate!

Answer
Dear Shelley,

The key thing here is what you call his "shyness" and the face that he is 45 and has never married or, ostensibly, "dated."  This is not a good sign.

Generally speaking, it doesn't work very well when the woman does the initiating.  I suppose it's worth a try to contact him, but this "so incredibly shy that he hasn't dated anyone all these years" -- this is NOT a GOOD SIGN.  Think about that, more than about the money issue.

All the best,
Susan Dunn
www.susandunn.cc