How does a girl get the shy guy she wants if he's too shy to let her win him over?

For whatever reason, shy guys seem to "self-sabotage" relationships with new women. I am really into this shy guy and its almost like he is avoiding getting to know each other. I know I'm not the first girl to run into this problem with him but he has been married before, so she got through his shell somehow. How did she do it? Anyone out there that knows how to capture this rare breed of man? Tips, ideas, personal experience. I'm open. Thanks!


Most Helpful Guy

  • I have to wonder how he's so shy even after all you've gone through. Are you positive that he likes you? Are you sure he counted your last "date" as a date?
    I can kind of see from his perspective as I used to be one of the shyest guys you've met. I can still be shy. However, the last four and-a-half years of my life have put some iron into my personality (joined the military) thereby reducing my shyness, but never eliminating it.
    The only way to get him is to open him up. That was how my girlfriend got me. I was very stubborn in opening up to her until she (metaphorically) backed me against the wall and pried me open like an oyster.

    Right now he is probably content with the current situation. You need to be more forceful, but don't run him over as well. That is easier said than done, and you'll really have to play it by ear.

    • Great insight! Neither one of us called the date a "date".. But he picked the time, the place (which was very intimate and candlelit), and paid the check. He's the one who brought up seeing me again.. twice, when I didn't respond the first time.

      I would consider myself an extremely observant person so I don't think I misinterpreted his interest. I do however think he was at a loss as to how he could pursue things further so I took the reins. But no luck.

      At this point, I've given up trying anymore. I stopped talking to him altogether a couple of weeks ago. Then he surprised me by "like"ing one of my posts on Facebook. Which is totally out of character because we have been fb friends for almost a year and he has NEVER acknowledge my wall, EVER.

      I don't know what to think anymore :(

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    • No. You haven't wasted your time on this man. He is probably interested in you, but he has some issues he cannot overcome to pursue that interest.
      Everyone has issues, some which can cripple.
      This may benefit him as much as you. What this man needs is to go through the crucible of life's experience, to rise above his weaknesses and overcome his shyness. He needs to understand that waiting passively will not get him all that he needs or wants.
      You yourself have also learned something. You may have learned the limitations and attitudes of shy men. You may have encountered what works/doesn't work, and how to tackle this issue in future.
      I can't readily say what either of you took, or will take, from this.
      I do agree that if he steps up and wants to pursue this relationship, you should accept. You are doing what you need to do; live life as it comes; and what happens, happens.

      All I can say is that you took something from this.

    • That makes a lot of sense. Thank you:)

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What Guys Said 4

  • Have you heard that saying "Be careful what you ask for, you might get it"? The quiet shy guy you describe could be having difficulty interacting closely with others and so presents to the world a rigid, automatic persona pleasant on the outside, but seething with hidden conflicts. Maybe he has developed a phobia about women. But that's just a side note and you can trust your own judgment.

    I will give you powerful tools to help you gain control of your environment: Practice your social skills, which will improve with use. You look good, smell good, and dress good. Smile, eye contact (drop your eyes occasionally, but keep looking at his neck, chest, et cetera). Friendly touch his arm during casual conversation. Ask his help or opinion on a subject he may know about. Have inoffensive conversational subjects ready so you know what to say to keep him talking. Nod yes or no appropriately as he speaks (umm, uh huh, oh!). Break your conversation long enough to give him time to speak. So, you've approached him through the five senses with your pleasant femininity. If you can do so without awkwardness, invite him for coffee, movie, dinner and so forth. Once he responds positively to your efforts, then you can take charge and gently tell him what you want of him. You will do all this because you want to.

  • You need to make the first move. The shy guy isn't ever going to do it first unless he's backed into a corner. I would know, I am one, and the most courage I've ever mustered up to ask a girl out was the very day before my high school prom... through a text. I still cringe to this very day about it.

    • We went on a date once. I tried subtle moves, not so subtle moves, and nothing has worked. He still messages me but its like he's hiding behind his texts.

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    • How do I "back him into corner" and get him out of his shell?

    • Positive feedback can get a shy guy to break from his shell. Shy guys are shy because they're afraid. They're afraid anything they do might get disapproval from the person they like because something devastating happened in their past. In order to reverse this, they have to get positive approval from the girl whenever they do something that show's they actually tried to muster the courage to do. This builds their repertoire of courage and their ability to build it up faster, but be careful, because all of this can go crashing down with ANY sign of negativity from you. If he eventually gets the courage to give you a compliment or get a little closer to you or ESPECIALLY ask you out, you have to accept it. Any amount of disapproval could shatter any of the courage you helped him build up to that point, and it certainly would destroy his moral if you denied a formal date.
      I don't know how you could back him into a corner yourself. I know I was because I had a deadline.

  • Sounds like you're going to have to just ask him out. Saves him from having to do it himself and after you make the first move he might feel more comfortable around you.

    • I have already been out. It was amazing! That was 4 months ago. We still talk occasionally but he has kept his distance since then. I don't really know why because he has had a crush on me for years.

  • There you have it, "He's been married before" some lucky girl was able to get through to him and believe me the shy guys are most likely keepers. She probably messed it up some how and i know for sure he won't be trusting any girl easily, if you truly want him, you have to show him that you're on a totally different scale than the previous girl. Men tend to be hard to fall in love but believe me, when we do, it becomes our only weakness in a sense; its the only thing that can break us unless, he is an emotionless tools.


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