Do "Shy Guys" need a BOLD Woman to be the Pursuer? How BOLD should she be?

He's shy and NEVER initiates anything.. but I'm totally smitten! He seems to always be happy to hear from me but because he is so reserved about his feelings, I am terrified that I might be over stepping my bounds (as the woman/pursuer) so I only message him like a couple times a month. This is getting me NO WHERE! If you were/are a shy guy, could you give me some ideas of how you wish a girl you like would pursue you? Or perhaps she already got you and you have a story of how she accomplished breaking into your shell? Please share! Thanks :)


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Most Helpful Girl

  • You can't beat around the bush with shy guys, you have to be direct about what you want. Some shy guys are easily frieghtened like deer, so be blunt and forward without being crude.

    Simply ask him out on a date. A legit date. Don't use code words like hang out or chill, use the word date.

    After the 2nd or 3rd date ask him if hell be your boyfriend

    Bada being bada boom, simple.

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What Guys Said 7

  • Well, I'm just a teen but I hope I can help. In real life, or with people I know in real life I can be very shy. No shy guy is really shy, though. You just need to find a way for him to be comfortable when talking to you. There is a key to every guy's heart, and like most people think it's not usually food, hehe.. Anyway, you just have to find out how he really is. Like you said, break into his shell. Try to find out what he likes. That's always a great move with shy guys.
    Maybe he likes metal music?
    Maybe he likes romance books?
    Horror movies?
    Ask him, and if you have something in common just talk about it. Should be a step forward to making him open up to you.

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  • I think shy guys do yes. Not so much shy, but they're not extroverted. Guys in general prefer women to initiate in communication because if guys did it it would be regularly throughout the day and they wouldn't want to put the woman off or come off too needy. On the other hand when a girl contacts her SO it's always welcome. It doesn't need to be imaginative simply initiating the chat when you're free to let them know this is a good time and you'll be responding if they message. You can talk about anything, simply how your day's been or what you plan to do- guys love to hear anything from their SO's- apart from heavy bitching.

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  • Yeah, you need to be doing at least once a week. Maybe not everyday, as that can come on too strong.

    Invite him to some group things. Then invite him to something where nobody else shows up. And then say, well, I guess I finally got you on a date - since nobody else showed up. Then see how far you can push it. If you enjoyed the date, don't I get a kiss?

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    • If he's really shy a group of random people might be a little sketch compared to 1 on 1 ^

    • Hey, if you can get him one-on-one then do that. But won't be able to sneak it up as a date if you do that. So you'll have to go with moving into his personal space, and touching him, etc.

  • Well girls are pickier than guys so they should be logically in my opinion haha.
    If he's that shy you'll obviously have to initiate until he gets comfortable, if you want to know if he's even interested ask him out face to face, texting is so impersonal.

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  • ya especially more if they are inexperienced

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    • Can good looking guys be inexperienced? Or even shy for that matter?

  • yeah just get on top of him and ride that thang. hell enjoy it trust me.

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  • Get him out.. you can't talk much over text.

    Invite him out to something simple as coffee or some small event where you 2 can still talk. Or go for a simple walk with him and talk to him so he can slowly open up to you.

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