Four women in four cities take on 365 dates between them. Follow their adventures and misadventures.

54. For Richer or Poorer – Mr. Needs Tough Love

This is Rachel’s date 2 with Mr. Needs Some Tough Love. Read their date 1.

You know your date did not go well when one of the most positive things you can say about it was that the guy paid.

But for me, and the guys I go out with, this is expected and understood. I have actually only paid for a date once – with Mr. VIP only because it seemed appropriate after all he had done for me.

There were a lot of things Mr. Needs Tough Love did not “get” that night, including why a guy should not make sexual innuendos on a second date or talk about a woman he dated, puking all over herself.

But, he did understand this:

“Guys grow up knowing that, most likely, they will be responsible for making the most income. It’s like paying for dates. We have to do it,” he said.

Interestingly enough, he said this in response to an idea I had been toying around that defies such gender stereotypes.

“So, I have this exciting career and it’s not that I don’t want to have kids ever,” I said. “But doing so anytime soon seems like it’d put a halt on my career and my travels. So, what if I were the primary breadwinner? Like I’ll go out and do it up big and he can stay at home and cook dinner and take care of the kids…”

“Or, you can get a nanny,” he said.

Oh, absolutely.

But, in that moment, there was something that appealed to me about being the “sugar momma.”

Maybe there is something about the personalities of these high-earning alpha males I have been dating that just does not do it for me anymore.

As Mr. Needs Some Tough Love rambled on, I noticed he had chocolate fudge all over his bottom lip, which reminded me of Mr. Man-Boy. I liiiiiked him and he was the opposite of a high-earning alpha male.

But who am I kidding? I want a man who earns! Could I be open minded enough to fall in love with NYC’s next stay-at-home dad? Or would I feel deprived?

At least that night, I was not falling in love with anyone – another date with another guy I could never see myself kissing.

Have you ever had a date that made you question something you have always wanted in a guy?

Has a series of unsatisfying dates caused you to change your criteria in a partner?

How has going on a handful of bad dates in a short period of time affected you? What do you think?

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  • Julie

    Last time I had a series of unsatisfying dates I went on the path of
    least resistance. Texted my ex and ended up fooling around with a
    guy-friend. And a complimentary feeling of emptiness and regret

    • Rachel Russo – Ms. New York

      Ah, yes, Julie. Sometimes it seems like we ladies go back to our exes
      just because they seem better in comparison to the other men who attempt
      to date us! Seems like such interaction is always chased with an
      emotional hangover….

  • http://www.facebook.com/gregfigueroa85 Greg Figueroa

    So how is it understood and expected that the guy pays for the date? Do you tell them beforehand?

  • http://www.facebook.com/gregfigueroa85 Greg Figueroa

    So how is it understood and expected that the guy pays for the date? Do you tell them beforehand?

    • http://twitter.com/RachelTRusso Rachel Russo

      Hi Greg, In Manhattan, among most social circles, it is just understood that when a guy asks a girl on a date, he pays. Most men I date immediately reach for the check or slap down a credit card. Guys have told me: “Women don’t pay” when I was younger and had tried to pay before I knew this was the general dynamic. I would never tell someone beforehand. 

  • http://www.facebook.com/profile.php?id=9102604 Brian Lynn

    If it was a dinner date, I find a woman more attractive if she offers to pay for something small later in the night (e.g. a drink or dessert somewhere else). Great way to show that it wasn’t about getting something for free…unless the guy is a creep :)

    • 3six5dates

       That sounds pretty fair!