Paid dating, take 2

I had a couple more thoughts after writing this post.

First, I realize that in one little phrase – “if we hit it off” – I skipped over a giant portion of the process of reaching a mutually beneficial arrangement. In fact, I hit it off with very few of the women with whom I met. Sometimes, this was because I revealed myself not to be interested in showering the women with gifts and money; in others, it was because there simply wasn’t chemistry; often, it was both. One woman I remember particularly clearly seemed incredibly promising – we totally hit it off, riding around in a cab for an hour or so after our first date and fooling around prodigiously as we drove. But she was unmoveable off her high price tag, and I was uninterested. She then turned on me and started sending quite hostile messages, about how I was looking for the wrong thing on the wrong web site, etc. Eventually, I had to block her, because she honestly was harassing me.

And/but she wasn’t entirely wrong: I was looking for women who were looking for more than just money. And that was a rare, but not unknown, quantity.

And second, I left out a fair amount of thought about the women’s experience. In a post to come, I’ll delve into that. And talk a bit about a funny exchange I had with a woman friend of mine.

Her response to that post?

“Your seeking arrangement post made me laugh.”

I asked why.

“My friend is on that site and I had a threesome with her and her sugar daddy a while back.”

So I’ll tell you a bit more, both about my thoughts, and about her experience, and about my reaction to her experience, in the coming days.

Stay tuned!


  1. ohh.i’ll be cheap (just for you). pay me in orgasms.

    why would you want a lower price for something like that? i don’t get all. because what you’re describing is prostitution. no matter what you call it. “paid dating”. or is it not that forward?

    1. Wait, what don’t you get? Why there might be a disagreement over price? Why I call it “paid dating” and not prostitution?

      Fwiw, I think it’s prostitution. I just think paid dating is a certain subset of prostitution.

  2. Yup. I think it’s rude to ask for a discount when you’re with the person and getting hot and heavy.I’d be pissed if someone asked for a discount. I think that’s the sorta thing you work out before touching.I can see why you would think it’s a subset of prostitution but I think those girls are just better actresses. And thank you.

  3. I think chemistry is important no matter what. I can’t see what would be the point of paying to have sex with someone who didn’t turn you on…. however, I have a feeling trying to lower the charge during the ‘date’ could well kill off any chemistry that might have been there.


  4. There’s an anecdote about Winston Churchill. A woman he is speaking to says she would consider sleeping with a man for £1mil. He asks if she would do so for some derisory sum. She is scandalised; “Sir, do you take me for a prostitute?” Him “We have already established that Madam, we are merely haggling over price.” Or words to that effect. If you’re in business you can expect some day to have to haggle with a customer. To be indignant seems a little fey.
    I read the other post. ‘Compensated dating”. Made me laugh out loud.

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