2. All the Single Ladies

ALL THE SINGLE LADIES

PENELOPE

I kissed a boy for the very first time in the second grade. His name was Daniel, and he had these sparkling blue eyes that made my seven-year-old heart swoon.

I can't remember a time I didn't have a crush on a boy since.

But they never seemed to crush on me back. I'm always the buddy, the cool chick, the friend without benefits. The nice girl who's a bit too big to be arm candy, but lots of fun to pal around with.

What that made me was the master of unrequited love and a mess of lack of confidence. I always kind of thought I was pretty, but that didn't seem to matter if I was also chubby.

Until I started working for Kelsey Best. Yeah, that Kelsey Best. The plus-size, body positive, badass popstar who is changing the way the world looks at big girls one song and a half dozen platinum and multi-platinum records at a time.

Kelsey changed my world even before I became her assistant. When she won the second season of The Choicest Voice, I cried. Literally. Like tears streaming down my face, gulping sobs, crying because never in my life had I seen someone who looked like me stand up to the fatphobic people of the world, like that one judge on the show, and be lauded and praised in front of the entire world.

I couldn't sing to save my life, but I felt seen. I felt represented. For the first time, I felt like my size, shape, and what the scale said didn't have to dictate my life.

Then I went back to school the next day and was reminded by the cheerleaders and their football player boyfriends exactly why I'd struggled with self-confidence with just one insult and a whole round of laughs in the student center cafe.

I quit college that same week, and it was the best thing I ever did.

Working for Kelsey these past few years has been like a crash course in self-love and confidence. Don't get me wrong, I still have my moments of doubt, but they're fewer and farther between. Kelsey's unwavering belief in herself, and by extension, in me, has been nothing short of transformative.

Lately, I've even been toying with the idea of dipping my toes back into the dating pool. Watching Kelsey and Declan together, so utterly in love and supportive of each other, has awakened a longing in me I thought I'd buried deep.

Sometimes, I catch myself daydreaming about finding someone like that for myself. Someone kind, funny, and devastatingly handsome... like any of the Kingman boys, if I'm being honest. Everett, in particular, with his easy charm and killer smile, has starred in more than a few of those daydreams.

But that's all they can ever be—daydreams. Dating my boss's fiancé's brother? Talk about complicated. Besides, a guy like Everett Kingman was so far out of my league, he might as well be playing a different sport entirely.

I shook off those thoughts as Kelsey and I arranged the last of the rubber snakes around me on the living room floor. We'd been at this for hours, trying to get the perfect shot for her social media tease.

"You know," Kelsey mused, adjusting a particularly realistic-looking cobra near my head, "it's too bad we couldn't use a real snake. That would've been so cool."

I laughed, careful not to disturb our carefully crafted snake pit. "Yeah, because Pooh would love that. Your little wiener dog vs. a giant python or anaconda—now that would make for some viral content."

Kelsey giggled, her eyes sparkling with mischief. "Oh god, can you imagine? Poor Pooh would probably try to adopt it as some kind of long, scaly puppy."

"Hey, don't knock it," I said, grinning up at her. "I think owning a snake would be pretty awesome. Kind of sexy, even. You know, in a dangerous, mysterious way."

"Penelope Quinn," Kelsey gasped in mock scandal. "Are you telling me you have a thing for snakes? Should I be worried about leaving you alone with all these rubber reptiles?"

I rolled my eyes, trying not to laugh and ruin our setup again. "Oh please. I just think they're cool, that's all. Besides, after this morning's excitement with Everett, I think I've had enough snake action for one day."

Kelsey's eyes lit up at the mention of Everett's name. "Oh my god. I still can't believe he dove in to rescue you like that. Who knew Mr. Tough Tight End was scared of snakes?"

I felt a warmth spread through my chest at the memory. "Yeah, it was pretty heroic," I admitted, then quickly added, "In a hilarious, over-the-top kind of way, of course."

"Of course," Kelsey agreed, but the knowing look in her eyes made me wonder if I'd been a little too transparent in my admiration.

Before I could dwell on it, Kelsey's phone chimed. "Ooh, that's probably Dec," she said, reaching for her phone. "Let's wrap this up and grab some lunch. I'm starving."

We cleared away our serpentine photo shoot, and my mind kept wandering to wondering what Everett was up to at practice. And if, just maybe, he was thinking about our snake encounter too.

Oh no. Nope, no, no, no. That was a dangerous train of thought that went to nowhere. I'd be better fantasizing about any one of Kelsey's exes over any of the Kingmans. That would be too damn weird.

She glanced at the screen and her eyes widened. "Ooh, it's Neith."

Kelsey had just signed on with the De le Reine agency, and Neith had been a revelation compared to The Mosquito Who Shall Not Be Named. We'd all clicked right away, and honestly, since Neith was also a bigger girl, she just understood Kelsey and her goals and plans so much better than any other agent or manager ever had.

Never once had Neith made me feel like less than because I was an assistant either. In fact, she'd told Kelsey to make me her new record label's vice president. I was going to tell her yes. Soon.

I watched as Kelsey's expression morphed from curiosity to shock, then pure, unbridled joy. She started bouncing on her toes, her free hand flying to her mouth as she listened, her eyes and smile getting wider and wider.

I knew what this call was. I'd be surprised that Kelsey hadn't realized, but she was so deliriously happy these days, that work wasn't the all-encompassing weight on her shoulders like it used to be.

"Are you serious? Oh my god, yes. Yes. Thank you so much." She was practically vibrating with excitement.

I raised an eyebrow at her, silently waiting for her to tell me all about her nomination. Kelsey just shook her head, still listening to whatever Neith was telling her.

Maybe she'd gotten a couple of nominations, maybe even album of the year. After what felt like an eternity, she hung up and turned to me, her eyes shining with tears of happiness.

"Pen," she said, her voice trembling, "I've been nominated for six Grampys."

For a moment, I just stared at her, stunned. Of course she was.

"Oh my god," I literally screamed, jumping up and down. "Kelsey, that's amazing."

We grabbed each other's hands and jumped like kangaroos on crack together, squealing like teenagers. "Six nominations? You're going to clean up at the Grampys."

"I can't believe it," she said, wiping happy tears from her eyes. "Album of the year and best pop vocal album, best pop solo performance, song of the year and record of the year for "Next Chapter" and Best Song Written For Visual Media... Pen, this is insane."

She spun around in a circle and declared, "We need to go shopping and find the perfect dresses for the red carpet."

I nodded enthusiastically, already mentally cataloging the plus size designers we could contact. Kels would need several dresses for the night. There weren't just the awards, but the after parties too. I looked around the snake-messy living room for my tablet. Then her words fully registered. "Wait... we?"

Kelsey looked at me like I'd grown a second head. "Of course we You don't think I'd go to the Grampys without my best friend and right-hand woman, do you?"

My heart swelled at her words, but a knot of anxiety was already forming in my stomach. "But... the red carpet? I don't know, Kels. This is your moment, and that's a lot of cameras, a lot of eyes..."

"And you're a natural on camera," she assured me. "Oh, and of course, Dec will be there too. Which means..." She trailed off, a mischievous glint in her eye.

I knew that look. It never led anywhere good for me. "Which means what?" I asked warily.

"Which means we need to find you a hot date to walk you down the red carpet too."

And just like that, my world tilted on its axis. I was right back in that college campus coffee shop with everyone staring at me, everyone laughing and pointing directly at my chubby butt.

"A... a date?" I stammered. "For the Grampys red carpet?"

Kelsey nodded enthusiastically. "Yeah, it'll be so great. We'll both have our arm candy, looking fabulous in our knockout dresses. The press, and more importantly, the Besties, will eat it up. Ooh, let's do a whole campaign to encourage the besties to dress up and show themselves off too. There will be so many beautiful bodies all over the internet, it's going to be epic."

My mind was reeling. Just this morning, I'd been cautiously considering the idea of maybe possibly dipping my toe back into the dating pool. Now I was supposed to find a hot, celebrity-caliber date for one of the biggest nights in the entertainment industry, and positively represent plus size women in front of the universe?

"Kels, I don't know," I said, my voice small. I hated that the remaining little bit of negative body image issues I still had chose this moment to rear their ugly heads like a mythical hydra. No matter how many times I cut off those nasty insecurities, they popped back up.

"I'm not sure I'm... I mean, who would even..." I trailed off, unable to articulate the tornado of insecurities whirling through my mind. An ugly, dark rock sank right to the bottom of my stomach, and it was made of self-doubt and lava. I was incredibly embarrassed that Kelsey, my friend, idol, and patron saint of body confidence had to see that I didn't believe it all for myself.

"Hey," she said softly, taking my hands. Kelsey's excitement dimmed a bit as she noticed my distress. "What's wrong? Talk to me, Pen."

I took a deep breath, trying to organize my thoughts and not sound like I hadn't been paying attention to her life's mission all this time I'd been working for her. I simply could not tell her I was afraid of being laughed at and made fun of and shamed for what I looked like. I couldn't.

"It's just... I was barely ready to think about dating again. It's been a while, you know? And now you're talking about finding me some hot celebrity date for the Grampys? I don't know if I'm confident enough for that. What if I make a fool of myself? What if no one wants to go with me? What if?—"

"Whoa, whoa," Kelsey interrupted my spiral. "Slow down, honey. First of all, any guy would be lucky to have you on his arm. Second, we've got time. The Grampys aren't for a couple of months. And third," she squeezed my hands, "I've got your back, okay? Always."

I nodded, grateful for her support but still terrified. As Kelsey pulled me into a hug, my mind raced with possibilities and fears. A red carpet date? Me?

What had I gotten myself into?

Okay, okay. It was all going to be fine. I would pull myself out of this body confidence spiral. I didn't actually believe that I was unattractive. More importantly, I would be absolutely honored if some woman who didn't believe she was beautiful saw me on the red carpet and saw a bit of herself in me.

If I held onto that, I could fake it until I made it. I knew I could. I'd just had a momentary freak out, and that was okay. Every woman in the world would worry about what she'd look like on the red carpet in front of all those cameras.

"Are you sure I need a date?"

"No. You can walk the red carpet however you want to, Pen. Anything you want to do will be great, amazing, perfect. I promise." She pulled me into a hug. "I didn't mean to stress you out by implying that you had to get a celebrity date. That was insensitive of me. There's nothing wrong with representing the single ladies."

She began singing Beyonce's "Single Ladies" song and dancing around, kicking the rubber snakes. Wiener the Pooh bolted into the living room and barked along to the song and bounced around like she was doing a little doggy dance too.

I gave in and danced and sang along too.

Even though Kelsey said I didn't need a date for the Grampys, now I wanted to prove that I could get one. I did need to dip my toes back into dating. It was time.

I'd probably have more freak outs along the way, and that was okay too. As long as I sucked up my courage and continued to work through my fears and worries. Because that was the way to overcome them. Face them head on.

It would help if I had an Olympic-level dating coach to help me do this. And I knew exactly who to ask.

The love guru himself.

Everett Kingman.