Your new lover is an ex-kept woman (or fellow). Do you care?

In My Humble Opinion
1

The spiritual successor to this thread, I suppose.

Imagine that you meet Sean, an attractive, intelligent, and witty person whose gender and sexual orientation are compatible with yours. You’re single, and the two of you start dating. Sean’s a professional student who spends time between semesters travelling and doing volunteer work for various worthy charitable causes. One day you happen to see that Sean’s written a check to one of those causes for a hundred grand, making you realize that, despite his/her unspectacular lifestyle, s/he’s absolutely loaded.

“Sean,” you ask one lazy morning, “if you don’t mind me asking, how much are you worth?”

“I don’t know exactly,” Sean replies. “I think it’s about twenty million dollars in liquid assets, but there’s a lot more in real estate and stocks and so forth. About a hundred million, maybe. I’d have to ask the accountants.”

“So where did it come from? Did you inherit a fortune? Invent a new method for attaching aglets?”

Sean hesitates. Then, with a shrug, s/he says that the money was inherited from Chris, the person who paid for his/her first undergraduate degree–and who was, incidentally, a good forty years Sean’s senior. Sean was never in love with Chris, and says that even after knowing you for only a month, s/he cares far more deeply for you than s/he ever did for Chris, though that relationship lasted nearly four years. From Sean’s vantage point, the relationship simply the best way to pay for college; s/he never anticipated being left Chris’s fortune. Sean has never mentioned Chris before because some people have reacted negatively to the revelation that s/he used to be a kept woman (or gigolo). But Sean really likes you, and so wants to be up front about his/her past.

Does this revelation bother you? Do you still keep dating him or her? What’s your reasoning?

2

Having never dated anyone that rich, I dunno. I like to think that I’m a hip and with-it young person and that I wouldn’t care. I sure as hell have imagined how nice it could be to be a kept man. As long as Sean’s nice and seems to genuinely care for me, I don’t see why I would worry.

3

My bf used to take advantage of women like that too and it does bother me a lot. Of course, he doesn’t have $100 million to show for it though. That might make it a little more palatable. (Actually it wouldn’t really…I think being with someone super rich would just make me uneasy.) I wouldn’t break up with Mr. Super Rich over just that though. But I would be on the lookout for other things wrong with him.

4

Given that in this case I am a good 30 years older than Sean, this would work out rather nicely. :smiley:

Wouldn’t bother me a bit.

5

Sean doesn’t LIVE like the super-rich. The OP says his/her lifestyle is “unspectacular” (except for being that of a professional student) and that you didn’t realize Sean was rich until you happened to see the $100K check. So clearly Sean’s not living in a mansion and being ferried about by limousine.

6

I’d marry Sean that day. We get along and he’s rich? Why the hell wouldn’t I?

7

Yeah, and I like that about him, but I would still feel uneasy. That’s just too much money and I don’t think he deserves it (yeah, obviously Chris left it to him because she wanted to, but still…gross).

8

It depends upon other factors than those stated in the OP.
However, assuming those were acceptable, her history is in the past.
I would feel pretty good that she had the guts to tell me the truth.

9

I really can’t figure out why anyone would have an issue with this (except, I guess, for people who’d have an issue with any past sexual partners). So she has a lot of money and at least one slightly unusual relationship in her past? That’s just like every person I know, except for the “a lot of money” part. I’m in, and never give it another moment’s thought.

10

I would have more trouble with the extreme wealth discrepancy! I am by no means rich, and especially in the dating phase, I would be hard-pressed to not feel awkward when my idea of a worthy charitable donation is $50.

11

I wouldn’t care in the slightest, but **Anaamika **does make a good (if uncomfortable) point. Then again, money has never been a problem between me and people I know who are far less well-off.

12

Slightly unusual? Chris was 40 years older. And Sean was just using Chris. Very creepy.

13

Assuming the first month you knew Sean was typical, why would the fact that hewas so much wealthier bother you, given that he lived modestly anyway?

How do you know it wasn’t Chris was who using Sean?

14

As long as Sean and I were compatible so far, I don’t think this would bother me. Both Sean and Chris got something out of the relationship, and assuming they were both open and agreed about just what that relationship was, then why should it be skin off my nose?

For those of you who say it would, would it bother you if instead of the money coming from sugar momma/daddy Chris, it came from “I never met her” great aunt Sally?

15

Since I’m a heterosexual male, I’ll make it Shawna. Or are there women named Sean out there…?

Was Shawna’s benefactor aware that she was mostly using him for tuition money and never truly in love? Or was it more of a contractual relationship?

I would care because either scenario would not sit well with me.

Scenario A (Feigned love)
I don’t think I can trust anyone who can pretend to be in love for four years for their financial benefit at the expense of an unwitting victim. I find this scenario morally reprehensible.

Scenario B (Tuition for company)
That’s prostitution isn’t it? Would she have been willing to sleep with several Johns if she had not been lucky enough to have stumbled upon Mr. Jackpot?

The third added scenario of an inheritance would bother me a lot less. Actually it would be pretty cool, as long as she took care not to rub in it my face how much wealthier she was.

16

Chris might have been using Sean too, but I don’t see how Sean could not be considered using Chris for her money.

No, that wouldn’t bother me because he wouldn’t have been using her and wouldn’t have been in some creepy relationship with her.

17

Where is the poll? And the pie? I demand pie!

I don’t think I would have a problem with it. It really depends on what is going on with us.

18

Yeah, although I can’t decide if it would raise a lot of insecurity or self-esteem. Someone with that kind of cash really could be dating anyone they ever wanted. If they want lil ole me who is not bringing fame or fortune to the table, just a predilection for sarcasm and campy tv along with a kickass brownie recipe, that might be an ego boost.

19

Poll & pastry are right here. Except it’s chocolate cake.

20

Well, it could be interpreted to mean that Sean can be bought, or that s/he has (or can have) a mercenary attitude toward affection, sex, and/or relationships.

Or, having had someone think that it was worth literally millions of dollars to be in a relationship with Sean may have given Sean the idea, if only unconsciously, that s/he deserved or should expect similar deference in future relationships; Sean might not be a good candidate for an “equal partners” type of relationship.

Personally, I don’t know whether it would bother me or not, but I can’t be sure it wouldn’t, or that it mightn’t be indicative of things about Sean that would bother me.