Trying to figure out why I seem undateable?

So, I'm trying to figure out why I seem to completely fail anytime I'm interested in a woman. I don't fail outright either - the women and I have enough in common that we can talk, and I can even joke around with them and make them laugh sometimes. And There's a good, long, initial time where the woman in question and I can have long, meaningful conversations sharing complete thoughts. But eventually, it all goes to hell. Not in any kind of fight, but in them going off with another guy - often times, an idiotic tough-guy douchebag at that. Not just saying that either - they rely heavily on image, and seriously do dumb things.

But it's not about why they win in the end - it's about why I don't. All I can think of is to list good and bad traits:

For me:

-Idk if I'm good-looking, but I don't think I'm that bad-looking that looks are my problem
-healthy, nonsmoker, non-druggie, not obese
-I like to think I'm relatively smart
-I'm well-read and educated
-I have goals and aspirations
-I have hobbies and passions
-I'm a decent conversationalist and can talk about many topics well
-I like to think I'm kind, a good guy. I'm not looking to use women or be cruel. Also I'm real. I don't hide behind image, I'm not trying to be a biker, "gangsta", or some other kind of ridiculous macho man.

Against me:

-I'm currently unemployed. I know this is bad, and I'm working on it.
-I have hobbies and passions but aren't really good at them yet. I wasted a lot of time in my life and i feel I am really behind where I should be in life.
-I don't have a lot of stories, I haven't done a whole lot with my life. I didn't believe I could for the longest time, and only now am I starting to catch up.
-I don't know how to flirt/tease very well. I don't know how to create attraction or have much experience communicating interest or creating a sexual mood. I feel like a robot sometimes.
-Maybe not being a macho man makes women think I'm boring.

Any ideas?

Updates:
PS - I'm 27, going to be 28 in a little while. And I still haven't been on so much as a date, let alone a relationship, so it makes me think that there's something wrong going on. A lot of people are married by my age, yet no girl looks my way.

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Most Helpful Guy

  • Do things ever reach a physical level between you and the women that you talk to?
    Y'all have a great time talking, but is there any flirting going on?

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    • This could be the trouble. There have been times when the conversation has taken a turn towards things of a sexual nature. This one girl I liked, still do actually, once asked me what I'd do if she tried to seduce me. Don't know why she'd ask that.

      I'm not sure how to steer the conversation that way, though.

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    • Thanks for MH :)

    • Yea, no worries. It was a tough call. But you helped explain how to work with my specific situation a little bit in more detail.

What Girls Said 4

  • I would date you.

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    • That's sweet :) May I ask why? What do you think I'm doing right?

      I hope you're not just trolling me.

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    • I didn't read that book you typed though xD

    • It was just me trying to figure out my problem, describing the situation and listing what I think are my good and bad traits. Glad you like my music taste though. I think someone's taste in art and interests is a good window into who they are and what they're like. Even though tastes can always change over time or be added to. It's something to share and bond over, at least for starters.

  • Agree with NoblesseOblige...
    Need this! xD

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    • That seems to be the consensus. Well, at least we've narrowed down the cause of the problem.

      If you don't mind sharing, how do you prefer to be flirted with? How does a man tease well, in your eyes? What communicates interest to you, in a way that gets you to feel that way too?

    • Humor!
      This, to me, is the most important thing of all when flirting.
      Being funny (naturally, not forcing it or trying too hard) is what really establishes a bond between me and another person -be it a romantic relationship or a friendship.
      People usually underestimate humor as a personality trait. With that trait (and a little bit of courage) your game can go a looooooooooooooong way and get to the finish (her saying 'yes' to you asking her out) more often than not.

      The thing is, this is an individualized answer. I don't know what other girls think and how they feel about a guy approaching them this way, but it's my favorite type of an approach (maybe the only one I'll really respond to).
      Also, eye contact is crucial. A good eye contact can say a lot more than words can. So catch her eye before switching to humor and approaching. Just so she may prepare for what's coming and not be completely blind sided. ^-^

  • You sound great :)

    But it seems the girls you end up with are shallow :(

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    • @ArabianPwincess197 ,

      Awe, thanks a lot :)

      It wasn't that they were shallow, though. They could actually be really sweet. No, the fault is mine. I moved too slowly, or I just messed up. Sigh...

    • I guess it just wasn't meant to be. Hopefully you will someone much better and nicer who will compliment you in every way :)

  • Personally for me a guy that is 27/28 should be employed for me to keep an ongoing relationship. After years of dating guys potential, I've learn that in the end it won't work for my standards.

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    • Totally understandable. Like I said, I'm trying to do something about that problem. Wish me luck.

    • Good Luck! I think once you get that lined up your confidence level will sky rocket making you more attractive to girls.

What Guys Said 2

  • Number 1 problem: Not flirting, not touching.

    When I was wonder, I constantly had girls after me, but eventually it would just die out and nothing happened. Once I started flirting and being more physical, things all changed. Reading this book really helped me with that. http://howtoalphamale.blogspot.ca/

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  • This:
    -I don't know how to flirt/tease very well. I don't know how to create attraction or have much experience communicating interest or creating a sexual mood. I feel like a robot sometimes.

    You need this. ASAP.

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    • I think not knowing this stuff has already cost me dearly. I've started to read some of those blogs, but hope I can turn it around with this one girl. She was the one I mentioned on the other post.

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    • I remember you said the Dark Triad was a good place to start. I've begun looking into it. What else would you recommend?

    • Well you don't seem to need it. I think you just need to learn kino and sexual escalation.

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