Horrible Choice

I’m not talking about the pathetic U.S. Presidential campaigns.  

No, I’m frustrated, because I met this woman who I REALLY like, but because of my pathetically numerous failed experiences in dating and my pathetic track record of disappointing relationships, I’m now a very insecure man who’s extremely afraid of asking a woman out on a date.  

Ever since I was a kid I’ve had no courage what so ever in asking a girl out on a date, mainly because I was always the outsider who never fit in…the ugly duckling…which you can read about Here and Here.

Of course, over the years I gained a little more courage each time I asked someone out on a date, but after my last failed relationship I’ve lost all courage and confidence in asking anyone out.  

I have ZERO confidence.  

None.  Nada.  Zilch.

I really don’t believe that women have any idea how much they affect the mental and emotional state of men when they repeatedly reject us.  It really is devastating to not only our egos, but also our confidence and morale.  I think that’s why so many men need the false sense of liquid courage (or the internet) to even muster a fraction of the energy and confidence needed to approach a woman.  

It’s pathetic, I tell ya.  

And now…after years and years of repeatedly being told I’m unwanted . . . here I am . . . once again . . . trying to muster the courage and figure out a way to look at this woman and ask her if she would like to meet me for dinner, coffee or another activity.  All the while telling myself that it’s not worth it because this will end just like every other relationship I’ve ever had . . .  six weeks and a cloud of dust.  

That’s right…every single dating relationship I ever had ended after six weeks, and they ran away into the arms of another man who they eventually married within three years of fleeing from me.  

For the women who have run away…a blessing. . . 

For me…it’s a pathetic curse.  One I’ve had to live with all my life. . .   

sooo…ya.  There’s that.  




It’s pathetic how a lack of confidence and fear of rejection will keep me from taking a chance.  

rejection hurts




39 thoughts on “Frustrated

  1. Well, I can only offer my experience from the other side and I can tell you it is a mess for women too! Me personally as I have had my share of disastrous relationships and am currently just not dating anyone until I figure myself out a bit.

    For myself and many other women I know, we are dyng for men to take charge and make the first move and then follow through with a properly planned date. I think men for too long have gotten away with keeping things casual via quick text hookups vbecause we women have allowed this. This is turn spoils it for good guys like you becuause we tend to get cynical about all men.

    That doesn’t help you much, I know, just sharing my perspective. So what happened? Have you asked her out yet?

    Liked by 1 person

    • let me begin by answering your question… sadly, no. I didn’t ask her out because I found out that she’s engaged. I wasn’t all that upset when I found out, a little disappointed because she led me on by flirting with me, but not really upset. With that said, I thank you for sharing your experience from the other side. And what you said actually does help me more than you realize. It’s reassuring to know that there are women, like yourself, in this world who desire a man to take charge and follow through with the plans he’s made…so, thank you. I really appreciate your insight and wisdom. 🙂

      Liked by 1 person

  2. I always found dating to be the most frustrating thing in the world. And I always felt like I was on the other end of the deal. How do so many women control men? How did it always seem that men I dated had the upper hand. Looking back, I had more control than I realized. I had control over choosing who I wanted to like and how I handled it on my end. Didn’t make it any easier, that’s for sure!

    Liked by 1 person

    • ha! yes!! You are correct that dating is very frustrating. My biggest issue is knowing WHEN to ask someone out, and I always seem to be a day late…or in this case because I found out she’s engaged…a few years late.

      The older I get the more I don’t like dating and believe that families should play a bigger part in the whole match-making process. I’m not saying that I believe in arranged marriages from birth, but I think that families should have more influence when it comes to who dates whom. — just my opinion.

      Liked by 1 person

  3. This post makes me sad. Interestingly, I’ve been broken up with multiple times by multiple men within six weeks or so. After seeking some kind of answer, it’s always “I’m insecure,” or “I’m a sad lonely person, and you shouldn’t worry about me.”

    Please don’t be that kind of person.

    Liked by 1 person

    • Too late! I’m already an insecure, sad and lonely guy. lol..

      Okay…not so much. 😉

      I apologize that my post made you sad…I don’t like making people sad because that makes me sad. So, here’s a positive, uplifting comment… (I hope)….

      Quite honestly . . . and I hope you don’t mind me saying this. . .you’re a beautiful, strong confident woman. At least, that’s how you come across to me and those are extremely attractive qualities. You have a brightness about you that is infectious and makes people want to be around you, so I hope that you find someone who won’t take you or those endearing qualities for granted. 🙂


      I hope so.
      BTW…I found out that she’s engaged, so I never did ask her out.

      Liked by 1 person

  4. Just do it! I ask a bunch of questions every day. I get a lot of no and it sucks. but every now and the I get a yes and I feel great. After a while, no loses meaning. It’s just freedom to ask someone else

    Liked by 1 person

    • Thanks. I appreciate the encouragement, but I found out today that she’s engaged, so I’m a bit late…like two years too late. LOL.

      Anyway, it’s okay…if I had known a couple months ago when we began flirting, I would have stopped immediately…but then again…she probably should have backed off as well knowing that she was engaged. 🙂 oh well…life goes on.

      thanks again, Run…I appreciate your comment. 🙂

      Liked by 1 person

        • thanks, Peachy. However…

          I found out that she’s been engaged for the past year, sooo…asking her out isn’t going to happen. 😦

          I’m finding that the older I get the more difficult the whole dating thing is getting.


        • I know. I wish she would have told me, but I should have asked early on…and I didn’t.

          I did see a ring on her finger, but it wasn’t anything special…doesn’t even look like an engagement ring…just a plain old ring with a very small stud…in any case, we’ve flirted off and on for the past two months, and I wouldn’t have if I had known she was engaged.

          oh well…such is life. 🙂


  5. Dude. You’re NOT an ugly duckling. And not taking risks is worse than getting turned down. Take a chance…she’ll either say yes and you see where it goes…or she says no and you can move on. You know I care about you which is why I’m being tough on you. Pull yourself out of the negative hole – no one, including yourself, wants you there and it does you no good.

    Liked by 1 person

  6. No advice from me. I married, and we have children, and I am still trying to figure it out. I think it has something to do with hormones. Probably not a good idea to stick things like that in cattle.

    Liked by 3 people

  7. I know this feeling all too well. And I sadly lack the rainbows and sunshine nature that says “Go for it, it’ll be great!” But I will say that, if you want to, even just a little, you should. Because the longer you wait, the more it festers and makes the potential blowout much worse. That, and the “could’ve been”s grow more crippling if you don’t make the jump and someone else does and you’re in a position to be exposed to it.

    Best of luck, whichever way you decide to jump.

    Liked by 1 person

  8. I think the last “someecard” joke isn’t true. Love can be very painful but loneliness is worse. I would tend to view the rejection as recognizing a “bad fit”. Better to find that out sooner than later. You almost have to be a bit of a gambling man, because love is a gamble. When you hit the jackpot – there’s nothing like it! So don’t give up.

    Liked by 1 person

  9. Imagine all those yeses you don’t get if you don’t ask. And even if you’re on a six-week Groundhog Day, at least you’re getting the best six weeks of a relationship, you lucky sod!
    Stop being pathetic and go ask her out!

    Liked by 1 person

  10. I’m so sorry, irtfy. Rejection and learned helplessness stink. It probably sounds crazy, but the only cure I know for that is to fail faster, harder, and more often. Ask out every single woman you see. Young, old, ugly, pretty, whatever. You aren’t offering to marry them, just have coffee or something.

    You aren’t a series of failed relationships, you are now a relationship expert. The words we speak over ourselves have terrific power. It can feel a bit like a Jedi mind trick at first, but you have to speak confidence over yourself before it becomes real. Be Batman.

    Also, don’t think like all the girls who left you were fleeing you. Flip that around. You dodged a bullet. God was looking out for you. You got lucky. They were not worthy of you. It’s true you know. All that glitters is not gold. They always look so, so good, when they aren’t yours. Women learn about this too. That hot guitar player that seemed so desirable, once they get to know him, he’s actually just an unemployed bum who sits around playing guitar all day.

    Liked by 3 people

    • good advice, IB…however, I’ve failed fast…I’ve failed more often and I’ve failed harder each and every time. I’m going to be 45 years old very soon and the failing part just isn’t in me anymore. I’m tired of failing, and believe me…I’m no relationship expert. lol. that just sounds funny…

      Anyway, thanks for the advice…I know you’re meaning to be encouraging and it’s very sweet of you. 🙂


  11. I’m thinking that if this is what you’re thinking already then what have you got to lose from asking, you’re going to be no worse off that you are now, and if you don’t try you might miss out in something special.
    If it doesn’t work it just means she wasn’t the one.
    Usually we say grab that bull by the horns, but in this case catch that cow by the udders just seems wrong. For all us lonely hearts in the world man up and make the move!

    Liked by 2 people

Herd Mooings

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