What It Feels Like to Date a Rich Woman

My friend went out on a few dates with this multimillionaire.  I think she’s worth nine figures.  My friend was old enough to drink in California, so he’s around 21-25.  I think he’s 25 now, and I don’t remember exactly when this happened, so let’s assume he was 23.

He posted up an ad on craigslist saying he wanted to date someone.  Some lady responded to him but said that he had to sign non disclosures with an attorney before they met.  She also refused to send him pictures or anything too.  He was curious.  So he went over to meet the attorney and signed papers.

On his date, he was given bottles upon bottles of designer alcohol.  He was wined and dined and was provided a five course meal by a personal chef.  He was given like a grand or two, I don’t remember exactly.

I only remember this because when I was living on a sofa in Los Angeles, he was my roommate who had the room.  He was so excited to have a bottle of Cristal, Johnnie Walker Blue, and some other significant pieces of alcohol.

He went out on another date with her and she fixed his car and gave him another fat stack of cash!

Then she took him out on a trip to Vegas.  She promised him massive wealth and success, by promising him business connections and a lot of money.  All she wanted to do was sleep with him but he didn’t want to pursue the relationship further, so he got out of it.

I think the kicker here that made him leave was the fact that she was around three times his age.  Other than that, he seemed extremely happy with the relationship he had.

What do you think?

Originally posted on Quora.

Leonard Kim is Managing Partner at InfluenceTree. At InfluenceTree, Leonard and his team teach you how to build your (personal or business) brand, get featured in publications and growth hack your social media following.

0 thoughts on “What It Feels Like to Date a Rich Woman”

  1. Hmmmm makes me wonder….how would YOU have handled it. I think i would be tempted (if it was a man of course)…man I need to actually “FEEL” something for them if you know what I mean. So it wouldn’t have worked out with me either.


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