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How to ask a shy girl on a date? (The Right Way)

If you are reading this article, you are most likely having bad luck winning a date with that shy girl you've been eying for a while now. Or perhaps you just aren't sure how to approach the girl without making her too shy to comfortably be herself with you and accept a date.

The key approach to successfully asking a shy girl out will be the "Come To Her Comfort Zone" technique.

Why Do They Always Say No?
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When I first met the guy I am currently dating, I was very shy. He indirectly made it clear that he liked me, even though I rejected each of his offers to hang out in the beginning. He even went on to say that it didn't need to be a date, but more of a hang out. Still didn't work.

The reason I rejected his offers was because I did not know him well enough. I didn't feel comfortable enough around him. I needed to to feel more at ease with him before hanging out just the two of us. A shy girl needs to know what type of character the guy is before she can feel free to be herself with him so that she can know how much of herself to show without feeling embarrassed.

The Secret Technique

Most shy girls secretly know exactly what they need from a guy, so that they can overcome their nerves and go on a date with him. In fact, many of these girls are disappointed that most guys don't care to know a girl unless she is naturally outgoing. They often day dream of the day when a guy will finally notice and take the time to know them.

Here is how the technique works.

With most shy girls before you ask her out, it's always best to get to know her in an environment that she is already comfortable in. For example, where do you typically see her? At school? Work? group meetings? etc... If you know her from school, why not ask if you could join her and her friends during lunch? If you are getting to know her someplace she already feels at home, she is most likely to open up to you and be herself. It is the best way to get to know a shy girl.

Me and my boyfriend met at church. Church was one of my comfort zones because I knew the environment and I knew the people well. The first few times we hung out was at youth group. Once we started knowing each other better, the first step he took to gradually bring me away from my comfort zone was the following:
"The guys who end up dating the shy girls are the ones who are persistent and patient at pursuing them."

Our whole church had had planned to go see a movie at the theater, and he had asked me to sit beside him during the event. When I got to the show, he followed through with what he said, and reserved a seat for me beside him which prevented me from bailing on him, even though I was super nervous. See how I was in a comfortable environment with people I knew, and he simply asked me to sit beside him. Because he followed through by reserving me a seat and calling me over, I did! It might not seem like much, and I was very nervous the whole time, but is was so exciting to me and I loved it!

After that night, we started seeing each other outside of the church. Him and his family came to my house for supper and then we saw the Christmas parade together. Soon enough, we were going on real dates just the two of us!

To The Point
When it all comes down to it, not many guys actually take the time to get to know the shy girls. The fact that my boyfriend was so patient and persistent with me (unlike most guys) is what sparked my interest towards him in the first place. The guys who end up dating the shy girls are the ones who are persistent and patient at pursuing them, who know how to properly apply the "Come To Her Comfort Zone" technique.

Good luck with that special girl!

What Guys Said 20

  • My advice would be to have nothing to do with girls who won't meet you half way. You might 'win her over' but you'll be trying to 'win her over' every day of the damn relationship. Her shyness is such a handicap that she's in fact self centered.

    Avoid her. Move on and find someone who is actually able to give something back in a relationship.

  • 3mo

    I'm only 15, but please don't judge because of that.
    I've been going to this drama group outside of school for nearly 4 years now, and about 3 and a half years ago, I met this amazing, but shy and quirky girl. I only really get to see her once a week, and never during the holidays, so it is very difficult to actually talk properly, especially considering she is with her best friend at this group and I'm with my older brother.
    She goes to an all-girls school so she hasn't had much contact and time with guys and I'm wondering that this might be a factor into the awkwardness.
    We occasionally get to talk for about 5 minutes on the way home, but I don't feel we are actually friends, as I never have a good chance to talk to her. This realisation that I can never get close has led me to attempt abandoning that, and trying to go out with other people, and even in those relationships, I can't get over her.
    She can openly talk to me, but there can also be unnerving silence whenever I talk and I feel as if she doesn't feel like she has to respond. Could this be a sign that she is not interested or the other way round, like she's nervous to respond?
    I'm not sure how to approach her properly, as I am kinda shy too, so I've never really asked for her number, or to go out or anything, despite numerous attempts of telling myself I am going to do it.
    I've recently learned she is a perfectionist when it comes to exams and studying, and so I am wondering if it is a good idea to offer to help her revise/study but I'm not sure how to bring it up without it sounding weird. I skipped up a year, so I know most of the topics she would be doing in Maths/Science etc. but I want it to seem more like a firendly gesture than anything.

  • HI, please help me! lol

    im interested in this really shy girl at my uni. (we are both 22), i can't spend much time with her since we dont have many classes together perhaps 1-2/week and its hard to talk when others are around. I've managed to speak to her and become friends, but its hard getting her to go out, what can I do? she should know that i like her, I've given plenty of signs, not sure about her, she's too hard to read.(i have faint feeling that she does). this pursuing process has gone on for 4 months now. should i just tell her how I feel, or be patient and wait for her to open up more? I’m just worried that im not acting fast enough. Im running out of ideas...

  • great article! I was actually going to ask a girl out even though we've only know each other 2 weeks, I'll restraint back a bit now.

  • very nice article, I liked it a lot, but I would have to say that would apply to most girls yes? not just shy ones, since I believe all girls would like to be in their "comfort zone" when they are with a guy of interest

  • Ok so I read your article on on How to ask a shy girl on a date. Here is the deal, how do you get to the environment that she is already comfortable in. That would mean she would have to ask me to some sort of event. Right? How would I get her to ask me to an event? Because she is shy and I can't ask her to an event because she will be uncomfortable because she sorta only knows a few of my friends (not that well).

  • Too much work!?!? Meet us half way? Not a chance.

  • I have a question.. I know a girl and most signs point to her being shy.. How she and her closeset friend act and talk to me.. Kinda like they have a secret and don't want me to give up on her...But she puts up a front that she's not shy.. And flirts with every guy.. Well except me now... After I asked if she liked me.. She said.. "IDK".. Do shy girls do this but up a flirty front..? She gets really figity when I do anything.. But her other guy friends do it all the time.. Like picking her up..

  • What is the point? this sounds like a lot of work and not fun. This just sounds like another scream for entitlement. Basically the whole article is based on this "I am not going to put much effort, you will have to put up with my insecurity and you will have to do all the job".

  • Going to give this a try. Thanks.

  • That's kind of hard if you are not friends or you don't even know each other. The fact that you invite a girl out IS TO GET TO KNOW HER BETTER AND MAKE HER EASY AROUND YOU!

  • I have a problem with a shy girl I like at work. We went on one coffee date last fall and at work was still flirting with me, until she became cold around me the next day and rejected me as my other coworkers were gossiping to her and she got very uncomfortable. I respected her decision but she still gave me signs of interest. Now we have different shifts. I still text her and we tease each other but I only see her if I come by to visit at the store. How can I ask her out the right way?

  • I think we'd be very compatible, but I'm probably coming off as a confident, outgoing guy with no fears in the world, when really its quite the opposite. But I don't want to come off as dull and boring which I naturally am. I feel like at times she avoids me and I don't know what to think of that? When I'm with her sometimes it seems like she really likes me and other times her ambiguity throws me off.

  • I'm really losing patience because I've shown a lot of interest in her, even giving her small romantic gift once that she really enjoyed. It was a bunch of bananas and a sock moneky. She told me weeks before I did this, that bananas were her favorite fruit. It's hard to spend time with her in school because our schedules conflict. I have to actually try and find her at school during certain periods if I wanna see her. It's really making me go crazy. But I really like her because I'm shy like her.

  • Hi, I'm trying to get a shy girl to hang out with me outside of school. We're in college and she is a 1st year, I'm a 3rd year. She told me that she has never had a boyfriend and has told me things like "she tends to disappear when people get closer to her" She has shown interest in me by always complimenting my style and saying I'm funny and interesting. We have no classes together and she has no cell phone or social media.

    every time I ask her out she comes up with the small excuse not to.

  • I don't care what anyone says, I agree with kheserthorpe, don't waste your time with a girl that won't reciprocate interest, there are plenty more girls out there that aren't socially handicapped. Plus, this only works with shy girls, what if you think you're trying to get with someone you think is shy, but who's not interested? That's a big waste of time, and to adopt the persistence philosophy is only a recipe for failure in the larger scheme of dating.

  • That kind of feels like a contradiction. Just hear me out. I feel like I'm harassing a girl if I repeatedly ask her out and she says no. I don't want to be a stalker. How would I know if she's shy but interested vs she's just not interested?

  • This is great. Thanks for the article! The comments are great, too.


  • If its not too much trouble could you have a look at my question please as you seem to have a good knowledge about shy girls

  • This advice sounds very good. I'm in the exact same situation where I know the girl definitely likes me but I'm out of ideas and have given up. she is too shy and inexperienced.

What Girls Said 17

  • ..they will struggle with trying to overcome the frustrating complications their shyness creates. That is why if you are the type of guy who is patient and believes it is worth it to help that poor girl out, then go for it! Everyone has their weaknesses, some people have a hard time not getting too shy around their crushes.

  • Some of these girls are actually very selfless and super sweet. Some make great girlfriends, and are shy simply because they view guys they have crushes on as above them and it makes them blank out and get all shy when he's around. It's not something they can control in fact most of the time I think of how they wish they could have reacted. They try really hard not to let their shyness choke them up, but until they can see that the guy likes them too and/or that they get more used to him...;

  • loooooove this! if only my crush could see this

  • Yes, good point. This could work with most girls! Note: Some girls require less work than others and these measures might not be needed. Most outgoing girls will talk to you and accept a date and all you have to do is walk up to her, and ask her out. If that girl says no, than she might get annoyed if you come bother her when she is with friends or at work, because she's not interested. You need to be careful and use your instinct if you are to try this with a girl who is outgoing. Good luck!

    • Hi you seem to be giving good advice here so I hope you answer I'm not shy but I'm not outgoing either there's this girl who I like and I know she likes me though friends I'm in my senior year and I have like 45 days left of school I need to make my move now the thing is she's really shy but I've gotten to know here a bit im going to ask her for her number tomorrow but then what do I do I plan to talk to her and I want to ask her out before may 19 cause that's when we all go to DC and I want to be together then

  • Thank you for the comment :)

  • I'm a shy girl, and I've gotta say.. This would totally work on me.


  • How do you know her? Where do you usually see her and how old is she? This is all something to take into account.

  • If a girl is too shy to approach a guy, than the guy needs to man up and help her ease up to him. If your not willing, then fine, you just aren't gonna be dating that type of girl.

  • I hardly know any guys who are like this and genuine about it.Most of them just want to crack the shy girl open so to speak.I have yet met a guy who was persistant enough and respectable enough to do this.And the ones thatt are like this are usually annoying,immatuure and not all up there.

  • Well csk28, I do not personally know the girl, therefore there is no way for me to truly know what you should do. Either she is a nice girl but decided she only likes you as a friend, and now feels awkward with you because she knows she doesn't feel the same way, or she likes you and it is making her nervous. The best thing is simply to tell her how you feel and ask her if she feels the same way. You don't want to ask her out again if she doesn't.

  • Look, this article was created to help a guy ask a girl on a date in case the girl is too shy to accept one. There are cases (mostly with shy girls who are new to the dating scene) when a girl will flat out say no to a guy regardless of whether she wants to go out with him or not. I know this, because I used to be this way, and knew a few other girls who were the same. If you don't feel you need to help the girl feel comfortable with you before asking her on a date, than disregard this article.

  • That is a matter of opinion Moloch, we are all entitled to that.

  • haha! I feel your pain. I', glad you like it :)

  • I never said to continuously ask the girl out till she says yes. Its all about making her feel comfortable with you before asking her out. You do this by going to see her to spend time with her in an environment she already feels comfortable inn. If you follow the steps properly, if the girl is interested, it will be much more likely that by the time you ask her out, she will say yes. If she still says no after you have been following the technique, than it could be she is not interested.

  • Thanks! I'm glad you were able to find it helpful :)

  • Hi lovestruck, I wouldlove to help you out. Could you please specify what your question is?

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