I'm near 60 years old. "Harry" is near 70. I met Harry years ago. He was the CEO of a competing company. I lost my job a few years ago and I've never recovered my career. I've experienced age discrimination. Harry has never been married. I'm long ago divorced.
We met up again - in an elevator!
He asked me to meet him for drinks. We talked for hours, mostly about where the business was headed. We went to dinner. We started dating. No sex. We're having a good time and my feelings for him have grown.
I think Harry's terrific. He's a good guy. He's made a fortune and he's given away a lot to charity, especially kid's charities. He plays golf and is esteemed by his circle, mostly men. Some are widowed, some divorced, some have wives.
Harry is cheap when it comes to dating. Don't laugh Missy. He picks where we go. The drinks seemed watered down. That first dinner we went to a spaghetti restaurant. We go to fast food places. He looks for things to do for free, like recently this Smithsonian Sponsored Free Museum Day. We take walks in nature.
I want a man to help me financially. So one night while we were eating our burgers I lied and told Harry that I'd been a mistress before. It's not true! I did it so he'd think about it, me being his mistress. I thought to myself this man has never married and maybe he never will. I don't need to be married but I want love and I need help, at least until my retirement starts.
Harry said "Really, I had no idea," and kept eating.
What do you think? Should I backtrack and tell him the truth?
Babe from Kansas City
MISSY ANSWERS
Babe, you make me laugh!
I've been thinking on this and I wonder if Harry is as rich as you think he is or where this cheapness is coming from. Could be that he's testing you to see if you will like him and enjoy his company even if he's not spending a lot on you? I've heard of some rich people doing that. I've also heard of them not spending a lot because they know you don't have it to reciprocate and don't want to embarrass you.
If he's doing these cheap dates to test you, then you failed.
Sorry Babe, but you shouldn't have lied, especially not to provoke a reaction from him or to put the idea of him supporting you on the table. Maybe I'm being too harsh. So you lied about being an experienced mistress BUT YOU DID NOT LIE ABOUT YOUR INTENTION, which is to be supported, at least for a while.
I have this feeling, I could be wrong, that Harry thinks of you as a friend. He may also be communicating that to you by picking up the tab on your friendly encounters, just acknowledging that it's easy for him. Wouldn't you feel bad if you found out that when he's DATING he spends plenty?
So many people are now working at jobs that are beneath them. People are not working in their areas of education or expertise. There is nothing to be ashamed of about an honest days work, but I understand you are not able to live as you had, and not only that but your self esteem has taken a plunge because you're not fulfilled at work.
Babe, I think what I would do is test this relationship yourself by becoming a bit less available. Let him miss you. When he suggests you go and do something, go less often. Really, friend or lover, no one likes to be on call or taken for granted. See how intent he is on having your company. Be busy at work.
I also think it's OK to ask him if he knows of anyone who is hiring or if he could refer you to any of his business associates for work because you want and need to be more fulfilled and make more money. I would not suggest to him that you be his mistress again. I would drop that subject. Is there a good time to tell him you lied? Probably not.
Missy
PS: I you have a Question for Missy, please leave it as a Comment. Missy considers all Comments before publication and changes all names used (even if you did already!).
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