Date #1| Results: Failed

I was anticipating last evenings date to be interesting.  The man had shown decent level of interest and our first conversation went well.

I sort of knew it wasn’t quite right for who knows exactly what reason, but none-the-less, I was looking forward to it.

He chose a nice bar that was crowded when I arrived, late.  Originally he suggested coffee and I requested alcohol and a later meeting time due to my work schedule and he was thrilled with the suggestion, so I knew he was a decent man to begin with.

He wasn’t “my type” upon first glance, and definitely too small and soft in general, but, again, I was willing to see how the night went.  When we secured a seat at the bar he pointed out there was a happy hour menu and asked for the types of drinks they had available.  Of course, I didn’t choose a drink from their limited selection of Margarita or Chardonnay and requested my usual Prosecco.  I saw eyebrows raise at that.

Other small indications highlighted themselves across the evening but them most obvious was his inference to the cost of things.  Money, as you know, is a trigger for me.  I have a bougie side and I don’t like when a man consistently speaks about an actual price tag of things or how expensive something is.  When he started talking about salaries and what he considered “excellent” for a man of a certain age, I knew I was in trouble. There would be too much disparity.

Now, when I start to sense that the match isn’t right, I move away from difficult or incompatible topics, much like I would handle a work discussion.  But he wouldn’t give up.  He persisted on certain topics and it only made me realize he had an underlying current of thinking “I expect too much.”  And, I’m sure I do, from someone like you. 

We parted with a friendly hug and his promise to catch up with me again. I didn’t say anything though I’m sure many would say “be honest up front” it just didn’t feel right to me. If he were to text I would be honest but I don’t think he’s going to. 

I went into the date with a very open mind and I wasn’t nearly as disappointed as in the years past. I didn’t drink to excess, I didn’t try to entertain myself and it was less than 1.5 hours together which is plenty of time to determine I won’t be seeing him again. 

Meanwhile my next date, planned for next Friday, is already looking to discuss vacation destinations. He’s planning on going alone but is now hinting that a couples vacation would be so much better. 

Sometimes you can’t win. 

Author: Madeline Harper

My journey through divorce and an emotional and sexual reawakening. Love, laughter, friendships, family and heartbreak included. And there is sex, lots of it, so close your eyes and turn the page if that's not for you! While I started this blog as an endeavor to journal my thoughts and feelings in an attempt to better understand myself, it has become an amazing platform from which I have met some of the most interesting and wonderful people in my life. My path is often crooked, but I hope you will share in the journey with me.

10 thoughts on “Date #1| Results: Failed”

  1. I like this post because you pragmatically approached this date with a clear head. He’s nice but you saw the red flags, so you aren’t ignoring them. You aren’t beating yourself up over the thought of him not liking you. You stayed sober and polite — just like a grown-up 😉 Well done!

    Liked by 3 people

    1. He sent a message after the date that while he had suggested coffee and I suggested a drink, I then did not offer to pay half even though I knew I wouldn’t be seeing him again. He was bothered that I didn’t pay my way. I did reply to tell him
      I had noticed the disparity in our measures of social Behavior and money and it was my expectation a man pays for the date. While I know many disagree with me here, that is how I feel. I knew my gut was right about the different opinions regarding money were dead on!

      And…thanks! I’m ready for my next!

      Liked by 2 people

      1. OMG – I was going to do a whole rant, but I’m taking a breath since I’m a bit hangry at the moment. 😤

        Bullet dodged!! Obviously his relationship with money is not compatible with yours. Perfect, you can forget about him & move on. He can find someone else to split the tab with. Kudos to you for being mature about the entire thing.


  2. He messaged you to day he was bummed you didnt pony up what… 20 bucks? Is he 17? I haves work mates in the US who know I make less so they always pick up the tab even though we are friends. I personally think whoever asks for the date pays. You suggested a better time/place but he initiated. I get you’re not totally on the same page but tjeres a level where 1st dates are about learning and if something is weird and you continue seeing them, you feel it out. If you don’t plan on seeing them its a lesson learned, boo hoo. Move on .

    Liked by 1 person

    1. That’s about what the bill was my $14 dollar drink and half of the $1 oysters! I can’t believe he had the balls to text afterwards but it shows how good my gut was in regards to the way he was about money…I feel like (after my x) I have a fine tuned sense of someone who feels differently about money than I do!


      1. That’s also the guy who thinks if he buys you good dinner he deserves good sex. Ha. If I had good sex for eberytime I cooked like a boss I would never get out of bed…..


  3. It’s interesting how people have different expectations when it comes to dating. I would never meet someone for the first time for drinks or dinner and NOT offer to pay for my own drinks/meal. If the gentleman insists on paying, then I’m happy to accept (and to be honest, most times they do) — but as I have no idea what their detailed financial situation is prior to a first date, I would never assume they could afford to pay for my particular wants and tastes. You are in an enviable position of having a very well paying job — but many are not. I totally support your desire to only date men who make comparable (or higher) salaries than yours, but — of course — I’ve never seen your dating profile. Do you mention that so that potential dates are aware and fit the bill?

    Liked by 1 person

    1. haha – I do tend to try and suss out the “right” criteria for dates and generally speaking, among my friends, the man footing the bill is common. I would not dare to mention it because I consider that impolite and an expectation. I have noticed that it’s a rare occurrence for a man to not pick up the bill. It’s only happened to me twice before and I’ve been single for close to 3 years now. I don’t think it’s simply about income, but how people perceive gender roles. As cheap as my x is, I never once in all our dating paid for a thing. So I have also learned that the ability to pay for a date doesn’t make the person “cheap” but indicate for me if they come from more traditional gender role upbringing.


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