10 Tips for Dating A Shy Guy …

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10 Tips for Dating A Shy Guy ...

You’ve found the perfect man, flirted to perfection and now you have a date. Sounds perfect, so what’s the problem? He’s shy! Shy guys might be cute and endearing, but on a date, it can lead to awkward silences and tension. There are ways to cope with this shyness, though! Here are my top ten tips for dating a shy guy…

1. Spend time as friends…


Shy men are often loud and confident with their friends, but find girlfriends intimidating and can’t help getting shy! Spend time together doing friend things, and not only will you get to know him but he’ll learn to drop his guard, too.

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  1. September 21, 2011 at 10:48 am Permalink
    Mayaboo says:
    I like a guy and we aren’t really talking to each other what should I do??????????
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    • September 21, 2011 at 10:54 am
      Denise says:
      Hi Mayaboo. Welcome to All Women Stalk!

      Why aren’t you talking to each other? Does he know you? Please share more details. Thanks.
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  2. August 15, 2011 at 5:24 pm Permalink
    kRshyL says:
    ^^ thanks for the information i gonna try it to my crush.. .
    coz he is shy, im gonna get his attention seriously.. .!
    i will not give up.. ^^

    .. . . i ... See more will write soon if what is the result.. ^^
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  3. April 11, 2011 at 4:27 am Permalink
    Brendon says:
    wow after just coming accross this as a shy guy I felt doomed, most of us shy guys are only like that in public places, online we talk quite a bit and we also talk ... See more more to people we know well just a tip
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  4. November 2, 2010 at 10:56 am Permalink
    Ashlee says:
    I love dating sweet, shy guys because you have to earn their trust and friendship. They don’t just give it to anyone, you have to be super special to get it. :) It is ... See more also a little bit of a challenge to try to read them and make them happy. Great tips!
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    • November 6, 2010 at 4:07 pm
      Michele says:
      I really like this shy guy..he’s gorgeous, it is a lot of work for sure, but soooooo worth it. I work with my shy guys and he only talks to me, his friend who ... See more works there and his boss, I love it, because he is so handsome.. I know he’s not playing me, I love it!
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    • September 21, 2011 at 10:41 am
      Mayaboo says:
      Me to I look forword to a guy like that
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  5. April 7, 2012 at 9:20 pm Permalink
    Ben says:
    as a guy I’m quite confused by this positive talk about shy guys. Why are we constantly being told how important confidence is for attracting women?
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  6. February 19, 2012 at 9:39 pm Permalink
    Greg says:
    I am one these shy guys you talk about. I am not a shy as I once was but the key for me anyway is I am shy at first because I like to feel ... See more someone out. See what is ok and how far I can go. It is important I feel comfortable before I let someone in. As mentioned trust is key.
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  7. October 24, 2011 at 10:25 pm Permalink
    Anonymous says:
    Making my shy guy happy is enough to make me smile (:
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    • October 25, 2011 at 12:36 am
      Denise says:
      Awww…. That is so sweet. I sure hope your guys knows what he has with you.

      Thanks for sharing that!
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  8. February 2, 2011 at 3:44 pm Permalink
    Michele AP says:
    I have currently started hanging out with a guy that is shy. He isn’t shy around his friends. Since we have a lot of mutual friends i know several funny stories i start ... See more talking about them and try incorporate a quesetion that he can maybe finsh the story to get him to losen up a bit! However for this to work you have to know something about him or his friends.
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  9. November 6, 2010 at 4:11 pm Permalink
    Michele says:
    Wow..Ashley’s comments are right on target. I feel special too and always let him know that I am lucky to have him in my life. It’s a challenge but if you can get ... See more him to open up to you, it’s a huge accomplishment and so worth the challenge especially when he is so freakin’ HOT!I’m happy with my shy guy, patience is the key.
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  10. April 10, 2010 at 3:26 pm Permalink
    Samantha says:
    Hey i have been dating this uber shy guy for a week. He’s the nicest guy but I’m very loud and love to laugh and a leader and he’s more quiet and a follower but ... See more we both like eachother a ton and havent talked much because we get nervous around each other so these tips are perfect thanks! :D
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    • April 10, 2010 at 4:03 pm
      Sheila says:
      Hey Samantha,
      I know it can be hard to make such opposite personalities work but there’s a reason why they say opposites attract ;)
      Good luck sweetie! I hope these tips help :)
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  11. February 26, 2010 at 11:05 am Permalink
    Stacy says:
    That’s really “hoping tips”. I am dating with a shy guy, i read this tips when i was already implied some of it. I can’t more agree with your tips… shy guy is very misterious, ... See more need sometimes to open up.. since i love him i have to accept to all of his personality..the first tip is very important.. now he is so different .. i find him as my hero now… your tips for sure enriched my weapon to be my man…thanks again
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    • February 28, 2010 at 11:39 am
      Sheila says:
      Hey Stacy,
      Awww! That sounds like a wonderful love story. Good luck to you and your shy guy ;)
      Thanks for visiting!
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  12. January 9, 2010 at 11:51 am Permalink
    Xannyyy says:
    I don;t know about this one. Shy guys aren’t my types as I’m very bubbly and out spoken!
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    • January 10, 2010 at 7:32 am
      Sheila says:
      Hey Xannyyy,
      Shy guys really aren’t my type either. I’m not the most outspoken person around new people but I like my guy to be a little smarter than me and shy guys just don’t ... See more cut it for me either!
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  13. December 31, 2009 at 1:41 am Permalink
    Piyanuch says:
    my date was a shy guy, but now he a is a non-stop talking with (only) me.
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    • January 2, 2010 at 7:29 am
      Sheila says:
      Hey Piyanuch,
      Lol! Is that a good thing or a bad thing? :p
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    • August 15, 2011 at 5:26 pm
      kRshyL says:
      oh… . that’s gOOd!! ^^
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  14. December 29, 2009 at 3:09 am Permalink
    Johanna says:
    If a guy is really shy, I prepare a list of questions ahead of time to ask, if the conversation goes dead. (But I of course don’t pull the list out of my purse and ... See more read ofof of it, I just memorize the questions.)
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    • December 29, 2009 at 6:24 am
      Sheila says:
      Hey Johanna,
      Lol. Yeah it would be pretty funny if you actually pulled out a list. Didn’t something like that happen in The Ugly Truth with Katherine Heigl? Imagine how freaked out the guy might get.
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  15. December 28, 2009 at 7:55 pm Permalink
    Fatima says:
    Very good tips. I never really dated a shy guy. I tend to be the shy one. But if I ever stumble upon a shy guy I will remember these.
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    • December 29, 2009 at 2:40 am
      Sheila says:
      Hey Fatima,
      I’m just like Rose and you. I usually end up dating talkative guys…who are more talkative than me anyway. I want them to work on me rather than the other way round ;)
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  16. December 28, 2009 at 6:27 pm Permalink
    Amy says:
    aww this post was so sweet (:
    for shy guys, i feel that opposites attract. a very outgoing girl may be just what he needs to bring him out of his shell.
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    • December 29, 2009 at 2:39 am
      Sheila says:
      Hey Amy,
      I think that would work for a while but like Jake said I think the girl would eventually get bored if the guy doesn’t get any better.
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  17. December 28, 2009 at 3:10 pm Permalink
    jake says:
    as a shy guy I liked your tips. they are exactly what I look for in a girl :) I have been struggling with my shyness for many years. Nevertheless, I have had some girlfriends ... See more along the way who know how to seduce a shy guy, even though they got bored or gave up later on. thanks for the post. you are are not going to believe it but maybe I myself can use these tips from now on :)
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    • December 28, 2009 at 3:26 pm
      Rose says:
      Well best of luck Jake (:
      I have a few guy friends who are VERY shy. But I’ve known them for YEARS so their girlfriends always ask me what they should do to get ... See more him to talk.

      Good luck with you shyness (:
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    • December 29, 2009 at 2:38 am
      Sheila says:
      Hey Jake,
      I really hope this post helps you come out of your shell. Don’t hide your awesome self under all the shyness :)
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  18. December 28, 2009 at 2:55 pm Permalink
    Rose says:
    These are some GREAT tips!! Personally, i prefer the outgoing talkative guys. Not overly talkative of course. lol. But to me i like a guy who can open up to me right away and show ... See more me who he is…and it makes it more exciting!!

    Plus, this seems like A LOT of work. But i mean if you find you really are interested in a shy guy. This is perfect!!

    Thanks for the post (:
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    • December 29, 2009 at 2:36 am
      Sheila says:
      Hey Rose,
      I agree. It does seem like a lot of work! And personally I don’t think I have the patience to try them out.
      But hey, sometimes if you really like the guy and ... See more think something amazing could come out of it, why not!
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  19. April 6, 2011 at 3:31 pm Permalink
    Miroo says:

    Hidden due to low comment rating. Click here to see.

    Poorly-rated. Like?: Thumb up 1 Thumb down 8
    • April 6, 2011 at 5:19 pm
      Sheila says:
      What if he’s a really wonderful guy? :D
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