Dating While Shy

How I overcame my shyness for my first date in, like, MONTHS.

I am a shy introvert (because no, those two things are not the same), and until last week, it had basically been a year since my last first date. To say I was rusty would be an understatement. But I’m in a stage of my life where I’m figuring things out, and didn’t feel like I was in a position to be looking for love, because, as cliché as it sounds, I was trying to find myself.

But I was passively perusing on Hinge, the latest dating app that’s trying desperately to provide users with a twinge more depth than your typical swipe right/swipe left Tinder experience. I had matched with someone, and we’d been talking for a while. It went on far longer than my Hinge conversations usually ever do.

When he asked if I wanted to hang out some time, my gut reaction was to make up some sort of excuse. After all, I’m not really looking for anything right now. Am I? If I’m not, why did I just spend the past 2 weeks messaging someone in a dating app? Isn’t meeting in person the whole POINT of this crazy exercise anyway? And on and on went the panicky internal monologue until I agreed to go on a date. Which, for me, was a huge deal.

In a lot of ways, dating apps are great for people who are shy. You can scroll through someone’s profile instead of having to approach them in a bar and say something flirtatious. You can talk to someone in a way that feels more comfortable so that you have at least some sort of rapport by the time you meet in person. It’s pretty amazing, actually — until it’s time to meet in person.

I had a lot of concerns going into my first date, and hopefully my experiences can either serve as advice, amusement, or, at the very least, proof that you’re not alone.

What if they get there first and I have to wander around looking for them?

I’m assuming that for most first dates, you’re probably going to meet at a bar, a restaurant, or a coffee shop. My single greatest fear was that this guy would get to the bar first and I’d have to wander around, trying not to stare too long at strangers, while trying to find him. My solve: text him something like “almost there, want to meet me outside in 5?” In reality, I actually got there first. Even better. I was checking a work email when he walked up, so the awkward “is that the person I’m supposed to meet, can’t really tell” fell on him, not me. Sorry, dude.

How do we greet each other?

A hug seems natural, but some people aren’t huggers. I’ve heard of people shaking hands upon meeting for a first date, which just feels a little too businesslike for my taste. Read the room, but a hug is a pretty safe bet. It makes you seem warm and comfortable, and establishes contact early on.

What if we have nothing to talk about?!

My guess would be that this is any shy person’s #1 fear going into a date — not having anything to say or coming off as quiet or boring. This was a big fear for me, too. But honestly, it almost always turns out fine. You’ve been talking to this person online, or you were set up by mutual friends, or whatever the case may be. Use the things you know about them as a jumping off point. When in doubt ask questions! If you’ve never met before, there should be plenty to ask about — work, their favorite restaurants, their go-to Netflix show.

Are we going to kiss at the end?

Every date, and every couple, is going to be different. If you feel like the date went great and want to end it with a kiss, that’s awesome (assuming both people are into it)! If the date doesn’t end in a kiss, that’s okay too. That doesn’t mean the person didn’t like you or that it didn’t go well. It can absolutely take more than one date to feel comfortable enough to kiss someone. So feel it out and go at your own pace — there’s no right or wrong answer.

In my experience as a shy person, online dating can be kind of nice, because at least you’ve established some sort of basis for the relationship. You’ve each found something attractive enough about the other person that you wanted to leave your houses and meet in person (which, who are we kidding, is kind of a huge deal these days). So if you can, take comfort in the fact that there’s a reason you’re both there. This person wanted to meet you!

If you’re shy and feeling too anxious to start dating, that’s okay. I hate nothing more than being told to “put myself out there.” You’ll do whatever you need to do when you feel ready. If you’re up to pushing yourself at some point, you will. If you’re shy and thinking of going on a date, try to be kind to yourself. Especially if you know it won’t be easy for you. Go at your own pace. People always say you may develop feelings or get a free drink out of it, but no matter how it goes, you’ll get a story. It’s true — try to have fun, but if it goes badly, you can leave early. You can retreat to your bed and do a solo binge of Tidying Up with Marie Kondo. Remember: dating should spark joy.

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