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Author: Kat Singleton
last update Last Updated: 2025-11-16 14:15:16

CHAPTER 2

EMMA

My grip is tight on the handle of my suitcase as I stop in the driveway of Winnie’s Hamptons home. My lips twitch as I look up, a wide smile spreading over my face.

“This will do,” I mutter under my breath, gazing at my home for the summer until the Uber driver interrupts me from my thoughts.

“Having a party?” he asks, handing me a tote bag with three bottles of wine.

I shrug. “Those are for me.”

The man quirks an eyebrow, staring me down with a speculative look on his face.

I blow out some air, trying to ease the awkward tension. “Don’t judge me, Simon. It was Simon, right?” I add on, worrying that I may have messed up his name.

“Yes, it’s Simon.” He turns around to get the rest of my luggage from the back of his sedan.

Simon hasn’t been my biggest fan since the moment he picked me up from the airport. I had a luggage carrier spilling over with suitcases as I waited on the curb for my ride. I was supposed to arrive in Long Island hours ago, but due to my flight being delayed twice, I’m arriving as the sun sets.

I won’t let the late arrival time and fussy driver burst my bubble, though. I’ve got three bottles of wine I spent way too much money on and a big empty house all to myself. Nothing can rain on my parade.

“I hear Pembroke is having a lavish, exclusive party tonight,” he notes, grunting as he drops my suitcase to the ground.

“Really?” I ask, intrigued. I’ve visited Pembroke Hills—one of the most expensive country clubs in the country—multiple times with my friends, but I’ve never gone alone. I don’t think I’d even be able to get in, but it would be a fun time…

“Yes,” Simon answers. “My wife loves to tell me where all of the events are taking place each night, even if she never wants to get out of the house to actually go to them.”

“There’s nothing wrong with staying in,” I say, taking my last piece of luggage from him. I hadn’t thought about getting all of these inside Winnie’s place on my own, but I know it might be too big of an ask to have Simon help me.

“Not at all,” he responds. “But you’re young and should be attending all the fun parties. If my wife, Trina, was here, she’d insist you go.”

I cock my head to the side. “It’s been a long travel day. Plus, I wasn’t invited.”

Simon closes his trunk with a loud thud. “Something tells me you’ll figure it out.” His eyes travel to my large pile of luggage I’ll have to lug inside. “Maybe try packing lighter next time?” He winks, softening his comment just a little.

Maybe I was wrong about Simon.

“It’s not in my personality to pack light,” I quip with a shrug. I must have an outfit for every situation, and I like to have options. I will always be the person who adds additional bags to my flight registration and will still manage to pay an overweight bag f*e.

Simon shakes his head at me. “Have a good night. Stay safe.” Before I can answer, he slides into the car and drives away, leaving me and my collection of luggage alone.

WINNIE

Hope you made it to the house safely. Let us know when you’re settled!

MARGO

Em, that’s Winnie’s way of telling you she’s worried about you.

WINNIE

Me? Worried? Never ;)

EMMA

You always worry.

Made it to the house and enjoying a glass of wine. Thank you again for helping me with my quarter-life crisis, Win!

WINNIE

Let me know if you need anything. Make sure to go out and enjoy yourself!

MARGO

This is where Winnie types a long speech about finding yourself…

WINNIE

Had to delete everything I just typed so I could prove you wrong.

I take a drink of my wine, staring at my phone as I wait for their next text. The house is a little empty without my friends here with me. Every other time I’ve visited the Hamptons, it’s been with them.

Any other time, you’d find Beck, Camden, and Archer seated at the breakfast nook, talking about boring business stuff that I didn’t care to pay attention to. Margo and Winnie would be hunched over interior design magazines, planning the next thing they’d decorate together. And Pippa would either be drinking straight from the wine bottle with me, or she’d be in the kitchen baking something new while she forced all of us to taste test.

Taking a deep breath, I place my phone face down on the counter and try to push away the feeling of loneliness. I think part of this summer in the Hamptons is me needing to be okay with being alone and learning who I am. There’s nothing like hitting rock bottom only to realize you have no idea who you are—and what you’ll do with the rest of your life.

My phone vibrates against the counter, but I leave it face down. Maybe the start of this summer of self-discovery will be less of me depending on my friends. Winnie and Margo are the best friends I could ever ask for. I met them in college when I desperately needed to find people who accepted me and showed me what it was like to be loved and cared for. I’ve allowed myself to let their choices dictate the path of my life. I followed both of them to LA after college and then moved back to New York when they decided it was time for them to come home.

This summer, I want to figure out where I want to be—who I want to be. I want to learn to love myself. And I want the start of that to be tonight.

Looking at the half-empty bottle of wine, I grab it by the neck and press the top to my lips. In a few easy gulps, I’ve emptied the entire bottle. “Ah,” I say, wiping my lips with the back of my hand.

I slide my phone off the counter, opening up the camera app and turning it to face me. It’s not the cutest I’ve ever looked in my life, but I feel inspired—and maybe Winnie was right about documenting it.

Letting out a nervous breath, I smile at the camera. “This might be the silliest thing I’ve ever done,” I mutter, tucking a strand of my blonde hair behind my ear. “But doing new things is all about making yourself uncomfortable, right?”

I pause, waiting for an answer before I realize that I’m talking to a screen—no one is going to answer me. Laughing, I shake my head. “My name is Emma, and I’m kind of a mess.” I take a break, tilting my head to the side as I look away from the camera for a minute. “Well, it’s more than kind of. I’m a huge mess. But I’m trying to get my life together, and I figured I’d document it. I’m going to use these videos as a diary of some sort. That way, when I look back—when, hopefully, I have my life together—I can see how far I’ve come.”

For the next ten minutes, I ramble on about my life story and everything I want to do this summer. I’m more open about things than I feel like I may be while sober, but it’s refreshing to voice all my fears out loud and address them by saying everything I want to accomplish before I leave the Hamptons.

By the end of it, I feel lighter than ever. I still have no idea what my future holds, but at least I’m doing something about it. I feel so good that I decide I actually am going to go out tonight. Do I have any idea if I’ll even be able to get into this fancy, exclusive party at the club? No. But it doesn’t hurt to try.

I film one last video telling my audience of no one but myself that I’ve decided to go out tonight and that I’ll keep them posted. I leave my phone on the counter and run to the room I’ll be staying in to get ready.

I have no idea where the night will take me, but I want an outfit that makes me feel hot as hell—and one that gives the illusion that I belong somewhere as fancy as Pembroke Hills Country Club.

And I think I know just the outfit I want.

Tonight is the first night of an amazing—hopefully life-changing—summer. And I’m ready to get it started.

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