The Shy Girl’s Guide To Dating

We don’t have to mask our shyness or pretend to be perfectly outgoing in order to have a good date.

By Keelia Clarkson3 min read
The Shy Girl’s Guide To Dating shutterstock

Attempting to date while shy – it might often feel akin to trying to bake cupcakes without an oven, or washing our hands without soap, or going to the store without shoes. Something really important feels missing, and it’s normal to wonder how on earth two single people can possibly meet each other, express interest, plan a date, and then find things to talk about on said date.

When you’re shy, it’s hard enough to admit to yourself that you like someone, much less ever have any sort of meaningful or extended dialogue with them in a romantic context.

This leads us to stay away from dating altogether, thinking it out of our comfort zone or too difficult for us to ever succeed. But is that the case? Is dating really reserved only for the golden retrievers of people?

I’d say not. Despite our nervousness, guardedness, and reticence, shy girls can date too. We just need a little help.

Every Shy Girl’s Dating Predicament: Meeting a Guy

The first hurdle to overcome in the dating saga of a shy girl is simply meeting the right guy. We’re not the type to confidently approach a guy at a café or nonchalantly ask out our new coworker. No – we need more time than that to get to know him, more assurance that he’s the type of guy we’d keep on liking beyond a surface level. So what are the safest ways to find such a guy?

The most common way to meet our boyfriend is through friends.

Well, probably through friends. Our friends aren’t just a collection of people we get along with – they’re reflections of what we value and the person we want to be. If we have good friends, chances are, they have other good friends whom we’d also enjoy. In fact, the most common way to meet your boyfriend is through friends.

But if that’s not an option, there’s a possibility we’ll come across a guy who shares similar interests and ideals at work, assuming we enjoy our line of work. This way, there’s an immediate point of connection we share with him and we’ll have had the opportunity to suss out whether or not he’s the type of guy for us by seeing him every day.

The Next Predicament: Getting Through the Date

So let’s say you’ve already secured the guy and the date. That’s already something to celebrate, but you’ll probably be too distracted to do that until you get through the first date – perhaps one of the most anxiety-inducing events for the shy girl. What do we even talk about? What if the conversation lags? What if we say or do something embarrassing? The list of things that could go wrong feels endless.

First off, it’s worth considering organizing a group date – involving a couple of your friends and their significant others – so as to take some of the pressure off yourself and your date. Whether it’s catching a movie, going bowling, or just all meeting up for dinner, group dates are a safe way to get more comfortable around a guy and come out of our shell in a group of mostly familiar faces.

But maybe a group date isn’t in the cards. How can a shy girl make a good impression on a first date? There are a few ways.

One way is by listening. It sounds like a simple concept (maybe even too simple), but when I reflect on the moments when I’ve felt overtaken by my shyness, I was completely in my own head and thoughts the whole time, mostly unaware of whatever was going on around me. When we make the effort to stay present and listen to the guy sitting across from us, he’ll automatically feel at ease – and who doesn’t want to feel that?

Ask questions – but not just for the sake of filling the silence. Here’s something that’s true about everyone: we love to talk about ourselves and our passions and our accomplishments and what makes us special. We want to feel unique and adored for our uniqueness. Asking questions and showing genuine interest will make a guy feel fascinating, and that’s a fantastic feeling. By making him feel like he’s captured our attention, he’ll likely want to return the favor.

Another thing to do? Maintain eye contact. I know – it can feel incredibly uncomfortable to hold someone’s gaze for longer than a couple of seconds at a time, but it’s actually a wonderful way to let someone know that you’re connecting with them and what they’re saying. Not just that, but direct eye contact can actually deepen attraction and create bonds.

Lastly, if we have anything nice to say, say it. It sounds so elementary to suggest saying something kind, but if I’m honest, I far more often find myself thinking something wonderful about someone instead of saying it. But when we notice something good about a guy, whether it’s his jacket, his smile, or the way he recounts a hilarious story, it’s worth telling him. Giving him a compliment will make him feel appreciated by us while keeping the spotlight off us.

Closing Thoughts

Although dating as a shy girl doesn’t always come naturally, it’s not anywhere near impossible, and we don’t have to pretend to be someone we’re not, either. Either way, dating will always have its fair share of butterflies, especially if we really like him!

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