How a Date Can Be Doomed Before It Starts

I have learned the hard way not to do a few very specific things when attempting to set up dates on-line:

  1. Do not go straight to texting, give yourself a little time to feel comfortable.
  2. Never go on a date after just a couple of text, learn something.
  3. Do not text endlessly until you meet the man, you need to get to know them in person and have something to talk about.

I have made these mistakes a number of times and it never works out.  It’s worth the little bit of effort it takes to text a little, chat a little, exchange more photos and then meet for a drink.

Know what you are getting, people.

I could write a much bigger list of not-to-do’s but this will suffice for now.  (and, honestly, friends, I am still making tons of dating mistakes so I would rather not highlight that fact at the moment!)  Today is about communication in particular, speaking to someone too much before a first date.

You do one of two things – either you set yourself up for a fall, or you set yourself up for a fall.  Ha.  That’s about it.

If you speak to them too much before the first date you could like them a whole lot. Then you meet in person and there is no chemistry.  Dead.  Over. Letdown.

Or, you can speak to them too much before the first date and start to hear things you don’t like and get you sort of turned off before you even meet, already starting the unintentional process of elimination in your head.

Case in point, I met a man on Bumble, we chatted a bit and switched to text.  We were due to go out in a few days, but he cancelled our first date with plenty of notice and rescheduled for a week later.  Although his reason for cancelling didn’t seem flaky, I just assumed he would disappear.  However, he did reschedule based on my availability for the next week.  A day or so after the cancellation he wrote again and asked me for a phone conversation.

Now, my friends and I disagree on the phone conversation thing.  Several of my friends say that only men in their mid to late 40s want to talk on the phone, those silly Gen X’ers (which means 1965-1984, so it actually covers more than 40 year olds!) However, my friends who state this neglect to realize that, while they may be younger than me, they are still in the same generational bracket!  However, they have a lot more dating experience in the Millennial generation (which the media designates as the worst generation ever!) and I suppose this is one of those crappy Millennial things – no one wants to speak on the phone anymore.

Anyway, I agreed and we chatted for a while.  There was a lot to like about this man, a whole lot.  He was handsome, well-educated, fantastic job, well-traveled, divorced, and super intelligent.  There was really nothing not to like about him, he met all of my criteria.  His communication was consistent and good and had just enough peppering of sweet.

Then we spoke.  I heard an almost-effeminate purr in his voice.  He called his son his “little angel.”  He is a creative type and I understand creatives tend to be a little airy at times but he spoke about the quality of his next relationship in terms of soulmate. I started to back-pedal because I interpreted all of this as soft.

Soft is not for me.

He asked me where I would like to go, suggesting a few places and we agreed upon a perfect location – hip and romantic at the same time.  A very cool locale.

So, except for the interpretation I made of him….he really is perfect on paper.

But now I have this earworm telling me he is soft and I don’t know how to get rid of that.

So, we shall see how this date goes and if an in person meeting changes my initial perspective.

He has been quite consistent to send at least one sweet text each day, but no more than that…which is a good thing.

There is a glimmer of hope.  He is a lovely man.

well, until I showed my dad his photo (just by way of conversation) and he frowned and exclaimed  “Maddy, he’s not for you, he’s gay!”

My Dad, the truck driver.





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.

30 thoughts on “How a Date Can Be Doomed Before It Starts”

  1. I once went out on a date with a man who had an effeminate voice. I thought he might be gay but I could be totally wrong. It just ruined it for me. I like a man’s man, and this guy just wasn’t it. Best of luck on your date. Let us know how it goes.


  2. You’re quite right on the level of conversation… I would suggest as well, and I don’t know if you do this, that an early quick drink (meaning 1, not a bottle!) or coffee is a good way to suss out some chemistry early on. I ensure I can’t stay long and he knows it in advance. That way, it’s not a major time investment, if it doesn’t go well you aren’t waiting a week or two to find out, and if it does go well it’s a nice way to have both of you wanting more.

    Liked by 2 people

  3. I would listen to your father.

    And you are correct with the not talking too much….I once chatted with a guy for far too long, really liked his personality, started to fall for him but then when we met in person there was zero spark. Nada. It was such a huge let down and then super awkward because he felt a spark for me and I had to explain to him that it just wasn’t there.

    Liked by 2 people

    1. Yea, that’s my fear is thatyou can like someone on the phone or in text but the real life chemistry just isn’t there. And it’s even worse in your situation where one person feels a spark and the other doesn’t! How did you end the date after that?


  4. I dated a guy Todd, back in the early -mid 90’s. He to had an effimanate voice that I too could not get over. I tried.. But a few dates in and I learned that his previous relationship was long term and with a male. Totally fizzled….😉


    1. I like a man’s man – tough and rugged in many respects – very masculine. My last guy was a cowboy through and through (he liked guns and cattle and the whole thing) and I know I am attracted to those very male qualities. I also like someone who takes charge and leads. Not controlling though.

      I think I would be shocked to find out about a previous relationship where my man was in a relationship with another man…that would throw me off. How did you handle that?


  5. I would have the same reaction. Did you see Grown Ups? The hunk at the pool came over to talk to the girls and when he opened his mouth … OMG! Hilarious. I think many of us have been conditioned to view the effeminate voice as a sign of softness (or weakness, depending on your perspective) and even as homosexuality. It can’t always be so, can it? I can’t wait to hear how this plays out.


    1. No, it can’t always be so – and this guy is really super in many, many ways…I just have to give him a chance and erase my preconceived notions before meeting him tmrw!

      I don’t recall if I have seen grown ups or not so that doesn’t ring a bell for me but I will check it out!


  6. I have definitely been turned off by the way a guy talks on the phone or in person. I know the feeling. I went on a date with a guy a few years ago, and I got lost on my way to meet him (I had never been to that place before, it was 45 mins away). Because I was driving, I just called him before the date to get better directions than my GPS was giving me and to apologize. How he sounded on the phone was a shock, he sounded more like a girl than a man. I later found out that he had congenital heart defects and had multiple heart surgeries and during one of them his recurrent laryngeal nerve was cut. I felt like a horrible human being knowing the exact reason that his voice sounded so feminine. Also knowing his medications and the fact that his heart was a ticking time bomb really turned me off. I trust my gut a lot, probably why I am still single. But if its bothering you now, its going to bother you in the future. Enjoy the date, but likely he’s not “The One.” 😉
    Great post!

    Liked by 1 person

  7. I am instantly thinking: “exactly HOW effeminate is that voice? Is it like: Well, he “. *doesn’t* speak like a lumber jack in the far North who drinks whisky every day”, or…. is it like “Omg, you sound like Britney Spears on her first album”!… ? 😀
    See…. it is the lack of men and sex does this to me. I am a lost cause, go on save yourself! 😉 Haha. I have my most pathetic post ever that I will post soon, I think, because of this… Back to the topic here: I think you are right to check him out if he has so many good things going for him. You can never know until you meet someone. The “90%ers”-guys, we just can’t afford to let thos slip without investigation….. 🙂


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