How To Ask A Girl Out (Without Dying When You Get Rejected)

Ask the girl out! Rejection can’t kill you.

“That girl, the one with the long hair and the button down and those badass black boots?”


“I have such a crush on her.”

“Then why don’t you talk to her?”

“Because she’s hot and cool and wearing badass black boots — that’s why.”

“Zara, that’s exactly why you should talk to her,” my friend Ryan said, rolling his eyes, reaching into his pocket for his phone. I watched his eyes light up as he began furiously chatting with someone on Tinder.

“Who are you talking to?”

A wicked smile spread across Ryan’s angelic face. “I’m asking this guy out.” He shoved his phone beneath my eyes. My eyes felt intoxicated by the sting of a smartphone light as serotonin rushed through my brain. I think that’s called addiction, but whatever. Who isn’t addicted to phones and tinder and pretty faces these days?

“Zara. Focus.”

“I am, it’s just this boy is so beautiful; I got lost in his face,” I purred authentically, because even though I’m a giant dyke, this boy was indeed so beautiful he elicited a real purr out of me.

“Well, I’m asking him out. I met him once at a party in The Pines, and I’d like to go on a date with him.”

My heart raced. My mouth went bone dry. My blood pressure rose. “Just like that? You’re asking him OUT?” I asked frantically.

“Yeah, what the hell is the big deal? You go on dates all the time.”

“I don’t ask people out.”

“Why? You think you’re too cool to ask someone out, bitch? Because I have news for you — ”


“Then what the hell is it? Why don’t you ask girls you like out?”

“It’s just not my thing,” I said, my voice and energy as freezing cold as ten thousand ice cubes landing against hot pavement.

Ryan primly smoothed his frizz-free hair and looked at me long and hard. I hate it when he does that. Not the long and hard staring part, the smoothing down of the frizz-free hair part. As an Ashkenazi Jew who is always battling against the relentless demons of frizz, I find it wildly offensive when satin-haired gay boys pretend to smooth fly-aways that simply don’t exist.


Later that night, I fell into a hard drunken sleep. In my dream, a woman with a stacked blonde bob and a Coach purse tapped me on the shoulder. We were sitting next to each other in the theatre, only there was no performance; we were staring at a beautiful stage framed by bright thick velvet curtains. There was no cast. There was no set.

“Honey,” the woman said to me.


“You need to get over your fear of rejection.”

“Huh?” I asked, bewildered but intrigued.

“See that empty stage right there?”

I nodded dutifully.

“Your fear of rejection stopped you from really going for your dreams as an actress. Which is why we’re sitting at a show with no performers. Everyone is too scared that they’ll put themselves out there and no one will like them, so no one has auditioned. You’re looking at your future.” She pointed to the stage. “A beautiful theatre.” She lit up a Virginia Slim cigarette. “That’s empty.” She exhaled. “It’s the people who breathe life into the theatre. What good is this fucking venue without people?”

“Can you even smoke in here?” I asked her.

“Doesn’t matter. Look around. No one else has shown up. The fear of rejection killed the theatre a long time ago, darling.”

“Huh,” I said really taking it all in.

“Name’s Sharon by the way,” the cigarette-smoking blonde-bobbed theatre goer said.

“Why are you here, then? If the theatre is dead?”

“I’m your guardian angel,” she winked at me. Her eyes were caked in Tammy Faye Baker style mascara.

I woke up.

The next night, I forced myself to go out to a lesbian gathering. I was pretty certain the girl with the boots and the long hair and the button-down would be there. It’s pretty easy to track down a lesbian. Our scene is small, even in New York. Plus she had RSVP’d to the event on Facebook, which I still believe is the best dating app there is.

I was a nervous blithering wreck as I adhered dark vampy lipstick to my trembling lips. I caked on the mascara like Sharon, my alleged guardian angel, had done in my dream. I looked like I had spiders firing out of my eyeballs, but it looked dramatic and sort of sexy and Sharon had seemed so confident, so it felt wise to mimic her makeup choices.

I resisted the urge to self-medicate my nerves with champagne or Xanax, because that usually leads to me down the dark path of making a giant asshat of myself. Plus, I was really trying to actively feel my feelings rather than simply numb them because my therapist had told me to do so. I’ll do anything an Upper East Side therapist tells me to do. They have great power over me.

I arrived at the venue alone, because I didn’t want to fall into my old habits of curling up into a tiny bar corner with just one friend, talking her face off all night and not engaging with anyone else. Even though I wanted to throw up and die from social anxiety the moment I entered the bar, I forced my lips into a smile and walked over to the bar. I wanted to ask the bartender for sixteen shots to quell the panic and fear swishing like a school of deranged fish through my bones.

Instead, I requested a civilized Sauvignon Blanc. I took a sip of the heavenly elixir as my eyes scanned the room. It was a teeming sea of all kinds of queer women. Brooklyn bohemians with their natural odors and vintage mom jeans juxtaposed against too-school-for-school graphic designing Manhattanites in blazers and designer denim. Suddenly, my eyes zeroed in on the long-haired girl in the button-down with the badass black boots. This time she wasn’t wearing badass black boots; she was wearing beat-up black sneakers. I surprised myself at how turned on I could be by the sight of beat-up black sneakers (purr).


Nicole Sashimi was right. I had no business approaching this girl I didn’t even know, only visually stalked from afar. She was too sexy for me. She was too sophisticated-looking for a wayward lez like me. I was setting myself up for rejection that would follow a shame-spiral that would follow self-loathing that would beget more self-loathing and self-loathing begets binge-drinking and binge-drinking isn’t the goal (anymore).

Then something spiritual happened. In my mind’s eye, I saw the empty stage. The empty beautiful stage. It broke my heart! Broke my heart MORE than the concept of rejection. What good is this fucking venue without talent? I heard Sharon say.

Even though my heart was racing faster than a cab speeding down the West Side Highway at 2 a.m., when the chances of getting pulled over are slim to none, I marched toward the girl in the button down. Even though I was sweating more than a teenager with illegal drugs shoved into her bra going through airport security, I approached her. Even though my voice felt trapped like a prisoner in my chest, I spoke.

“Hi,” I attempted. The voice had worked its way through the prison bars! It might have emerged three-octaves higher than usual, but babe. It emerged!

“Hi,” Said the girl in the button down. She smiled at me. “I’ve seen you around. What’s your name?”

She had noticed me?! She was smiling at me?! Maybe I wasn’t a repulsive heathen after all.

“Zara, what’s yours?”

“Ray. So Zara, what’s up?”

Thirty minutes later, we had found ourselves engaged in a deep and stimulating conversation. She had told me about her job, her pets, her opinions on current political affairs. She looked at her watch. “I’ve got to get home! I’m working out at 6 a.m.”

“Okay,” I said. DON’T ASK HER OUT YOU STUPID BITCH, Nicole Sashimi screamed into the air, swishing a martini around in a too-short, has-been Balenciaga bandage dress.

My mind went back to the empty stage. It’s the people who breathe life into the theatre, I heard Sharon whisper in a voice so kind it made me feel like I was being held by a mother. And even though my voice was shaking and my lips were trembling like a California earthquake and I was pretty sure I could taste vomit in the front of my mouth, I did it. I took a deep breath, the kind they tell you to do when you’re about to do something really hard and painful in a pilates class.

“I was wondering if maybe you wanted to get a drink or something some time?” I managed to squeak.

“I would love that!” Ray said, her brown eyes shining.

My heart leaped out of my chest. I felt my body float into the air and my spirit jumped onto the rafters of the ceiling where they danced happily. Nicole Sashimi pouted and walked away defeated. She looked washed up in that sad, desperate dress, her face weathered and weary from always being drunk and shouting mean things to me.

“But like, it would have to be as friends. I have a girlfriend.”

I felt my spirit crash to the ground. My heart that had been lingering in the air splattered against the floor. Nicole Sashimi ran toward me LAUGHING, wickedly. TOLD YOU SO! YOU UGLY ASS, DESPERATE HO! 

That’s when Sharon stepped in. I saw her in my mind’s eye. She folded her arms and rolled her eyes. You’re fine. She said, puffing on her Virginia Slim. You’re fucking fine. Rejection won’t kill you.

“That’s okay! I would love to be friends,” I said, meaning it. I suddenly felt a great wave of relief wash over my stiff limbs, the warm waves relaxing my tense joints. I had just asked a girl out! For the first time! And she said no! And I was fine! Why? Because rejection wasn’t this crazy force of nature that could physically kill me. So why the hell did I fear it like I fear death? A gun could kill me. A car could kill me. Disease could kill me. But rejection? Nah. It just bruised the ol’ ego. And I was starting to realize that I didn’t have to cater my life to my ego. For my ego was Nicole Sashimi! And she wore bandage dresses that haven’t been cool since, like, 2007. Why the hell did I put her on such a pedestal?

So that’s how you do it, kids. You just do it. You just ask her out for a drink or a coffee (dinner is a little intense for the first date, but that’s for another essay coming to GO soon!) even if you’re so nervous you think your teeth are going to crumble in your mouth. You can be scared shitless to do something and still do it anyway. After all, isn’t that what the essence of the theatre is? You think those actors aren’t nervous every time they get on stage?

And if you don’t “get the part” (as in she says “no” when you ask her out), you keep trudging along, little sister. It’s not that big of a deal, I promise. And honestly, despite what your ego thinks, her rejection probably has zero to do with you. She’s probably dating someone. Or about to move to Mars or Los Angeles or somewhere. Or maybe she’s not over her ex. Or in too fucked up of a place mentally to date right now. Or maybe you’re not her type — which is fine, because there are so many types of lesbians in this world, and you don’t want to be with someone who doesn’t appreciate the type you are. Since asking Ray out, I’ve asked a lot of girls out. Some have said yes, others have said no. One told me I was too femme for her taste, which was okay, because the woman I’m with now loves how femme I am. If I had lost my confidence because of that one comment, that would be a damn shame. Because it’s only one woman’s opinion. And you can’t base your self-esteem on one person’s opinion. (If you do, seek therapy! There is no shame in that; I go alllll the time).

Here are my final remarks: Getting rejected doesn’t mean you’re not amazing. It could mean a million things. But you can’t let the fear of rejection stop you from taking control of one of the most fun, affirming, romantic, wonderful parts of life: seeking love! So, what are you waiting for? Ask. Her. Out. I promise you that you won’t vomit on the floor in front of her because you’re so freaked out. You’ll feel like you will, but feelings aren’t facts, sister. I feel like I’m going to faint every time I go on the subway, and I never do. It’s my mind playing tricks on me. It’s my anxiety screwing with my head. But sometimes you have to push through the anxiety and get on the train. And then get off the train and go to the Hudson River and hop on a big ass boat and grab the freaking wheel and start steering that ship in the direction you want it to go on.

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