“Before I impress you with my cheesy pick-up line, are you ladies single?” he asks with a smirk. Aspen and I both laugh at his brazen approach and nod. “Are you my next workout? Because my heart is racing, and you’re making it harder for me to breathe,” he continues with an exaggerated wink. The taller man snorts a laugh, and I can’t help but join him. “I’m Oakley, and this is my best friend Parker.” The one who’s been speaking finally introduces them.
“Nice to meet you,” I say with a warm smile. His confident happiness is contagious, the kind of easy charm that instantly draws me in and makes me want to spend time with him. “I’m Sage, and this ismybest friend Aspen.” I gesture to where she’s smiling and holding eye contact with Parker.Interesting.
Oakley must notice too because he turns his full attention to me.“Well, Sage, is there any chance that I could get your number so we could all go out sometime?” he asks with another huge smile.
“Like a double date?” I clarify, really excited by the idea. Aspen and I have never been on a double date before. When I look at her, I’m surprised to see that she’s smiling openly at the suggestion, nodding slightly. She’s always been so private about her dating life, I’m shocked that sheactually seems to be happy about the suggestion. Maybe she has a very specific type and Parker checks all her boxes? Whatever the reason, I’m not going to question a good thing.
“If you both would be up for that,” he replies easily, glancing at his friend to see if he’d be interested. Parker nods before aiming his smile back toward Aspen.
“Okay,” Aspen and I say in unison, which makes us both laugh more. I can’t remember ever hitting it off with anyone so easily before. We all exchange numbers, and Oakley starts a group chat so that we can plan something.
“Well, we’ll let you get back to your workout,” Parker says. “It was nice to formally meet you both.”
“Bye, Sage,” Oakley says with another wink before they return to their routine. I could be wrong, but it seems like they might be showing off a bit. Oakley seems like a really nice guy, easygoing and funny. I hope that our double date goes well. It would be a dream come true if Aspen and I could be in relationships with men who are as close as we are.
The fantasy of what that could look like—spending all our time together, all of us being neighbors, maybe even raising families together if the thought of kids ever becomes less terrifying, or maybe we’ll continue to focus on our careers—it almost seems too good to be true.
May
“I haven’t beenthis excited about a date in a long time,” I tell Aspen as we ride the elevator down to the lobby of our building where we’re meeting Oakley and Parker. I’m full of energy and can barely stand still as I try to calm myself down enough to not scare Oakley away before we can even begin the date.
“Neither have I,” Aspen agrees. I almost ask her why, curious about what made her so eager to date Parker when she’s normally content to be single, when the elevator doors open and I see the guys waiting for us.
“We all match!” Aspen says brightly as she walks up to Parker, giving his forearm a light squeeze as she laughs at our matching boat inspired ensembles for our date on the water. Aspen loves dressing for a theme and coordinating outfits, which is why we’re rocking skirts, button-up blouses, and have sweaters tied around our shoulders. We look fit for a sailing commercial. Oakley and Parker fit in just as well with the more masculine version of our outfits.
Remembering how over-the-top Oakley was with his pick-up lines at the gym, I’m inspired to try to match that energy. “I’m not sure which look I like more, you hot andsweaty in the gym or all cleaned up here for a date,” I tell Oakley.
“Well, I can think of a few other looks I’d like to show you in my apartment,” he responds with an equally flirty tone and a wink, earning more laughs from Aspen and me.
We make our way to Oakley’s driver, who’s waiting out front to take us to the pier to Oakley’s boat. I know that these guys must have money to be able to afford to live in our building, but as we board the very nice yacht, and the the crew reminds us of the safety procedures before we’re escorted to a romantic dinner they’ve set up on the deck, I wonder if maybe I should have looked Oakley up before coming out tonight. Luckily he doesn’t seem like the type to expect me to know who he is, and the easy conversation on the way here confirmed how laid-back he seems.
There’s a table formally set for four with red rose petals contrasting against the stark white of the table cloth. Oakley pulls out a chair for me next to Aspen and takes his seat across from me. Having my best friend with me on this date is even better than I had hoped.
The four of us spend the meal laughing and learning more about each other. Oakley and Parker have been best friends since childhood, and they work for Oakley’s family’s hotel chain. I absolutely know of Caldwell Hotels, but, Oak, as he said I could call him, says it all very casually. It's obvious that he loves his family; every other story he shares seems to involve them, and it’s so refreshing to hear a grown man talk so lovingly about his siblings and parents.My family isn’t nearly as bad as Aspen’s, but I’ve always felt a disconnect from them. Our relationship is very formal and obligation based, not at all like what Oak’s describing.
We watch the sunset over the Chicago skyline and enjoy the fancy meal as Aspen and I tell them about how we met, and how we have been inseparable ever since. We constantly interrupt each other to add to the stories we’re telling, and I notice that Oakley and Parker do the same thing. I need to stop myself from running away with fantasies of us all growing old together, but I feel like they really understand us and our friendship in a way that a lot of people never could. I’ve had boyfriends in the past complain about how much time Aspen and I spend together or how often I talk about her, but I don’t think that would be a concern with Oakley.
“Wait, you’rethatAspen?” Oakley asks when she tells them about her career.
“Are you a wedding fan?” she responds with a laugh.
“Our company is revamping an old resort in Bora Bora to turn into an exclusive wedding destination,” he explains, full of excitement. “I’ve been obsessively researching wedding trends and your dresses are everywhere! That’s so impressive. You should be so proud of everything you’ve built.”
His comment isn’t flirty at all, he was equally engaged when talking about my career, asking about my favorite plants and what medications I’ve helped create from them, telling me how amazing everything I’ve done is. He seemslike a very supportive guy, and it makes me like him even more that he cares to know about my best friend and not just me.
“Maybe we could collaborate once the resort is finalized, feature some of your dresses in promo?” Oakley suggests, and Aspen lights up at the idea, suggesting which of her designs might be best for their venue.
I know they’re talking business, but I take it as a good sign that he’s so willing to make plans with us that far in advance. Like maybe he hopes that this could be the start of something real too.
When the chill from the wind over the water becomes uncomfortable, we move inside to the couches that are in the boat’s living room area as the yacht heads back to shore. In all the years that Aspen and I have lived in Chicago, we’ve never actually done the Centennial Wheel at Navy Pier, and tonight seems like the perfect opportunity.
“Can we ride the Ferris wheel?” I suggest as I we walk along the crowded pier past the restaurants and theater toward the city.
“Of course,” Oak says easily. “Sounds like fun!” The smile he flashes my way hasn’t faded all night, and I know mine has been equally present. Aspen and Parker seem to be having a good time too.
This is easily the best first date I’ve ever been on.
15
