The Shy Girl's Guide To Asking Someone Out On A Date

by Zara Barrie

Nobody believes me when I say I'm shy. But I'm actually really, debilitatingly shy.

I'm what I like to call low-key shy. I rock in-your-face, red lipstick and attention-seeking mega heels, and I'm totally shameless when it comes to sharing my most deeply personal, wildly embarrassing sex fails on the internet.

But when it comes to social interactions of any kind, I would rather just stay home and stare at the cracks in the ceiling. I would rather drink cold champagne alone at a dark bar full of old Upper East Side ladies than strike up conversation with a cool, new acquaintance.

I might be wearing a pink dramatic dress, but baby, don't let all that tulle and winged eyeliner fool you: I'm recluse.

My shyness really crawls out of it's shell when I'm dating.

Every single person I've ever dated has questioned whether I'm even into them, because I was always so timid about expressing my lusting and loving feelings. Your local lez wasn't asking any girls out.

And because, like many shy people, I have a loud energy, girls weren't asking me out either.

And you know what? I like to date. I like to have sex. I like sit across from a beautiful entity and gaze into their lovely face as it flickers in the subtle candle light over a three-course dinner at an uptown bistro. I can't help it. I'm a romantic. Purr.

But if no one is asking me out and I'm too scared to ask anyone else out, that just isn't going to happen. And it didn't for a while. For a long time, my weekends were spent spooning gay boys after salacious nights at famous gay mecca The Stonewall Inn.

I realized I had to get the hell over myself and my debilitating shyness, and ask a chick out.

And finally, somewhere in between the pitfalls of 28 and the triumphs of dirty 30, I learned to ASK A GIRL OUT, even though I'm secretly super shy. So I'm sharing the love, sister.

Here is the shy girl's guide to asking someone out on a dang date!

Wear a conversation starter piece of jewelry.

If you've ever stared at my chest (which I know you have, you dirty girl), you will notice that while I don't have the most ample set of breasts, I always have a gold handcuff necklace nestled between my clavicles, baby.

Why? Because I'm shy. And if you're shy, wearing a statement piece of jewelry is an amazing conversation piece.

So if I'm standing at the bar and I'm ordering myself a stiff drink and I'm making eyes at the girl three seats over, all I have to do is start playing with the gold handcuffs. Maybe I even go over to her and meekly say "Hi" while running my fingers along the cold texture of my gorgeous, golden necklace.

I swear to goddess, they will always ask about the necklace. Because it's provocative and it's different and it's sort of kinky —the perfect recipe for breaking the ice. I now have a lead.

If you're shy, it's imperative you have a lead, a pre-planned conversation starter that you're comfortable with so you can get warmed up and improvise from there.

"Hey. Woah, your necklace is handcuffs."

"Yeah, my best friend bought it for me for my 30th birthday," I'll lamely reply.


"I wear it because she lives in London and I miss her and I feel like she's with me whenever I wear it."

"That's sweet. I like it. Where did you get it?"

"Actually, this really cool blonde girl I know, who also lives in London — her name is Jessica De Lotz — designed it. She has a really sick jewelry line. You should check it out."

"Why do so many people you know live in London?"

"I'm actually British."

"You don't have an accent..."

And then I can launch into topics that really put me at ease: my English mother, my time living in the UK, if I prefer America over to the UK, does she prefer the UK to America?

By then, we've had at least an hour of animated conversation, which makes it SO MUCH easier to then ask her out on a date.

Ask him or her incessant questions about themselves.

My mother always told me the golden rule to overcoming the shyness epidemic was to switch the focus off of ourselves and turn it around on the other person.

For example, imagine me at the Cubbyhole (your neighborhood lesbian bar in Manhattan). I'm paralyzed with fear and I'm trembling as I press a tumbler of whiskey to my lips.

But I see a really sexy girl. I want to talk to her. I'm not wearing my conversation starter necklace. I have no wingman.

GAH, I'm spiraling fast. What do I do?

I take a deep breath, approach her slowly (not fast and predator like) and say, "Hi, what's your name? Do you come here often?"

"Hi, my name is Leslie the Lesbian, and yes, I come here a lot," she says.

"Do you live in the area?"

"Yeah, I live in Chelsea!"

"I used to live in Chelsea! What's your favorite restaurant?"

"I LOVE this place on the corner of 21st and 7th avenue called Elmo. Have you ever been there?"

And because people inherently LOVE to talk about themselves, they will be really excited to answer all of your rapid fire questions, and you'll be teeming with a newfound confidence because you won't be thinking about yourself for once.

Your energy will be on them, not on your narcissistic self.

FYI, we shy people are really surprisingly self-involved. We think everyone is judging us when really no one is even looking in our direction.

Once you've got the guy or girl passionately talking about themselves, they will start to become attracted to you because your interest in what they have to say is oddly refreshing.

After you've been talking for about 30 minutes, ask them out. It's not creepy at this point. You're like old friends because you've learned so much about them and they've opened up to you! ASK, girl.

Have a game plan.

Look, kittens, I get it. When you suffer from social anxiety, shyness or meek personality disorder like I do, you lose your words when you're nervous.

It's nerve-racking to ask someone out, so we always get tongue tied and start acting really weird, slurring our words and doing other deeply embarrassing stuff.

This is precisely why, my babes, you need a game plan. You need to pre-rehearse exactly what you're going to say and know it by heart. This way, when you black out as you're asking her out (not from booze; from nerves), you can go on autopilot and just say your lines.

Trust me when I say no one will notice that you've memorized your technique.

Now, some smug bitches might say "That's not AUTHENTIC. Just be yourself!" But those smug bitches aren't shy, so they don't get it.

If something comes over you and you feel like improvising, that's great! But make sure you have your asking-out speech perfectly down pat, so you can rely on it in case you have a meltdown.

Let me give you an example:

"Hey, so we've been talking for X hours and I think you're really interesting. Would you like to go out sometime? I know this awesome, really weird, but cool piano bar on the Upper West Side. I think you'd like it."

This way, I don't have to worry about coming up with something on the spot. I have the specific location already planned: somewhere cool but not trying too hard and not too bougie, but not too dive-y.

Own your shy.

Being shy isn't a bad thing. It's not like being a liar, a cheater or a wench. It's just a personality trait. And in this brash, in-your-face, let's-put-it-all-out-there culture, it's sort of sweet and endearing (so I've been told).

If you're feeling nervous and shy, don't try so hard to cover it up. Just own it.

"Hi, my name is Zara and I saw you across the bar and wanted to say hi, but I'm super shy, and I'm really nervous right now, so, um, HI."

It might not be smooth or graceful, but it's real. And I happen to think smoothness is way overrated. In fact, I usually run far away from sweet talkers because I don't find them authentic.

So just own your shy, weird, dorky self and the ladies (or boys) will be totally down. Because quirks are sexy. And being shy is not a flaw; it's a gorgeous quirk!

Quirks are sexy. And being shy is not a flaw; it's a gorgeous quirk!