by Max Monroe
I fondly recall being eleven years old and telling him about a fight I’d had with Emma—my best friend at the time. It was the usual catty girl stuff, but it was putting a serious rain on my adolescent parade, and Milo ended up being the only person in my house who was willing to listen.
After that, I trusted him.
And evidently, over a decade later, I still do.
“You didn’t date when you were at Stanford?” he asks and pops a fry into his mouth.
“A few times, I guess.” I shrug. “But nothing of substance. Most guys my age weren’t into a quiet night of Netflix. They wanted frat parties and bar-hopping.”
“Sounds like you’ve been dating the wrong guys, Mayb.”
I snort. “So, what you’re telling me is that basically every guy I came into contact with at Stanford was the wrong guy?”
“No.” He laughs. “Well, maybe. I don’t know who you were around. But a college frat party isn’t a great place to meet a guy, base case.”
I nod, though I suppose it’s happened for some people.
“And what about you?” I ask before finishing off my last bite of Reuben.
“What about me?”
“Are you dating anyone?”
“No.” He tilts his head toward his shoulder, and he smirks. “Nothing steady anyway.”
Another snort escapes my nose. “I’m not surprised.”
“What’s that supposed to mean?”
I laugh. “I mean I’m not surprised that you’re doing a lot of not-steady dating.”
“I didn’t say I was doing a lot of it,” he defends pitifully.
“Oh, c’mon, Milo,” I retort. “Back in the day, you always had a revolving door of pretty girls. When you were living with us, you once came home from one date, only to go on three more in the same night. With three different girls.”
He chokes on his water. “I did not.”
“You definitely did.” I nod, eyes serious.
“How the hell did I even fit that much activity in?”
“You and Evan were in your senior year of high school, and you said it was, and I quote, conditioning.”
“No!”
“Getting in shape,” I say, using finger quotes, “for prom.” The vivid nature of my memories of him would probably be more disturbing if he weren’t so horrified by his own actions.
“Well, fuck. What an asshole, seventeen-year-old-kid kind of thing to say.” He runs a hand through the dark locks on top of his head. “I have to admit,” he says with a tiny smile. “I’m a little disappointed in myself.”
I shrug.
“How in the hell do you remember this kind of shit?”
Because, when it comes to you, I remember everything. Sigh.
“I don’t know… So, yeah, it’s safe to say I’m not surprised you have fuck buddies now.”
“Fuck buddies?” he coughs, choking on his water.
“Yeah. A fuck buddy. Friends with benefits. That sort of thing.”
“Jesus,” he says through a chuckle. “I know what a fuck buddy is. Just hearing the words leave your mouth is…well, disconcerting.”
I roll my eyes. “Surely, I’m not the only person in New York saying fuck buddy.”
“Yeah, but you’re Evan’s little sister.”
A deep sigh leaves my lungs. “I’m not thirteen anymore, Milo.”
“That’s becoming more apparent by the minute.”
God, is he always going to see me as Evan’s baby sister?
What is it going to take for him to really realize I’m not a little girl anymore?
Suddenly, a lightbulb goes off over my head, and I spout the words without a second thought. “Why don’t you help me with more than just a job?”
“Help you with more than a job?”
“Yes. Help me navigate the New York dating scene. You said yourself I’m not really in touch with it anymore. I need someone with the inside track.”
It’s a shot in the damn dark, but one I have to take.
For the love of God, what if he says yes?
“Jesus,” he says on a sigh. “Help you date?”
I nod, and he scowls slightly.
I don’t know what to make of his expression, but after a few seconds of silence, he finally makes up his mind. “How about we start with connecting you with publishing houses and go from there?”
It isn’t a yes.
But it isn’t a no either…
Maybe he’ll be more open to it the more time we spend together.
“Fine,” I agree and point a teasing index finger toward his face. “But you better have some damn good connections, buddy.”
He winks. “Trust me, kid. I’ve got the right connections you need to land your dream job.”
Kid. He called me kid.
Every single piece of me knows I should be irritated, but for some strange reason, the way it flows off his tongue with affection and amusement, I don’t hate it all.
Milo
“Mr. Ives, your nine-thirty just called to say he’s running twenty minutes behind schedule,” my assistant Clara’s voice echoes from the intercom on my desk. “And just so you know, Caplin Hawkins has called twice.”
Of course he has.
“Thanks, Clara,” I respond. I haven’t spoken to Cap since I saw him at the hospital, but when it comes to him, there’s always a calm before the storm. He may be silent for weeks at a time, but when he decides to make contact, he always comes on strong.
Women, I fear, see it as part of his appeal.
I toss the file for GlossBit, the firmware company I was scheduled to meet with at nine thirty, onto my desk and pick up my phone to scroll through some of my publishing contacts.
I never have much time during a busy workday, so the twenty minutes I’ve just been granted is the perfect time for trying to figure out who would be the best fit for a connection for Maybe.
Or it would have been, if my phone didn’t start ringing in my hand.
Incoming FaceTime Call Caplin Hawkins.
Jesus Christ, this guy is like a bad rash.
Despite my better judgment, I tap accept and then transfer the call to my computer.
“Goddamn, Milo. You’re so hard to get ahold of, I was almost fooled into thinking you’re someone important,” Cap greets. “But, well…” He gestures at me and the computer and the fact that he has me on the line mockingly. “Apparently not.” I give him the finger, but he pays it no mind as he conferences Evan in.
On a sigh, I brace myself for the kind of call I can only imagine this will be.
Evan’s image shoots dramatically onto the screen, filling half of it next to Cap.
He smirks immediately at the sight of me. “I told him you had meetings all day, but you know he’s hard of hearing.”
“Only when it’s something I don’t want to hear,” Cap clarifies before laughing raucously. “Anyway, I think the point Evan is trying to make here is that you should always answer Old Cap-i-tain’s calls.”
“Isn’t it supposed to be the other way around?” I question in amusement. “Shouldn’t I be the one always trying to get my lawyer on the phone?”
Cap chuckles. “You would think that, right? I mean, I am the bigger deal out of the two of us.” I shake my head and Evan snorts. “But you know I’m a hands-on kind of guy in and out of the courtroom.”
“Ninety-nine percent of the women in New York can agree with that sentiment,” I announce.
“One hundred,” Evan corrects.
Cap’s grin grows wider.
“Like you bastards should talk. Up until the last few years, we were nose-to-nose with conquests. Evan’s got a thick chain around his ankle that links to only one pussy—”
“Hey!” Evan snaps.
“But what about you, Milo? You come down with a sudden bout of impotence or something?”
I smirk. “We can’t all continue to stick our dicks in everything that walks. Some of us have to grow up to be men, you know.”
“Grow
up to be men or grow up to like men?” Cap muses. “You know I’m a supporter of all walks of sexuality, bro. Say the word, and I’ll get suited up to walk in the parade with you.”
“Is it just me, or is everyone wondering how in the world Cap has yet to be disbarred?” Evan remarks.
“I haven’t been disbarred because I am a magical specimen of a man with skills heretofore unmatched in the field of corporate law. Hence the reason why I’ve been trying to reach you bozos all fucking day.”
“All fucking day?” I chuckle. “It’s not even ten a.m., Cap.”
“Do you want to hear it or not?”
“Hit me with it,” I respond.
“The contract with Birkin Industries is a go. It’s just a matter of signatures at this point.”
“Seriously?” I question, forgetting all about Cap’s inappropriate tendencies. Birkin Industries is an app development company we’ve been trying to buy out, but fuck, they’ve been resistant. So much so that I nearly gave up on the prospect.
“Consider Birkin your bitch.”
“Damn, Cap,” I say. “That’s incredible.” He really is incredible. It’s no wonder he’s so sought after.
“Well, shit,” Evan mutters. “And for a minute there, I almost forgot why you’re our lawyer.”
“You both know I’m the best lawyer money can buy, and I always have important shit to talk about.”
“A month ago, you interrupted one of my meetings with an urgent call.”
“It was an urgent call.”
“You called to ask me if you could fuck Kelly Booker.”
“Because she was your ex-girlfriend. I was sticking to Bro Code, bud. You should be thankful I’m such a thoughtful guy,” he explains. “Trust me, I made the mistake of accidentally getting up close and personal with one of Quince’s ex-girlfriends, and I felt like a real bastard.”
“Accidentally? How does something like that happen accidentally?”
“I didn’t know she was his ex-girlfriend until after the fact.” He shrugs it off. “I knew her name was familiar, but her face drew zero recognition. Honestly, for all I know, she had some plastic surgery done or some shit.”
“For the love of God, stay away from my sister,” Evan chimes in, and Cap tilts his head to the side.
“You have a sister?”
Jesus, Evan. Big mistake bringing her up. Huge.
“Yeah, and she’s off-fucking-limits.”
Cap grins. No offense taken at all. “But like, she’s free rein on nights and weekends, right? Like an old phone plan?”
“I swear to everything that’s holy, you better keep your hands—”
I’m not sure how Maybe ended up a part of this ridiculous conversation, but I cut him off in an attempt to change the direction of the conversation to something a little less volatile. “By the way, Ev, I had lunch with her on Saturday.”
“You did?” he asks, and a genuinely warm smile crests his lips. “How did it go?”
“Wait a fucking minute,” Cap interjects. “You’re telling me your sis is off-limits, but you’re thrilled when this bozo takes her out to lunch?”
“Because he knows she’s off-limits and is helping her out.”
Cap grins like a dirty bastard. “Oh, I’m sure he’s helping her out, all right…”
Internally, I cringe when I think about how Maybe basically asked me to help her get laid.
She said date, my mind interjects. Getting her laid is just what you were thinking about.
“Don’t be a sick fuck,” Evan retorts. “Maybe is trying to get a job with a publishing house, and Milo has contacts that could help her get a foot in the door.”
“And I don’t have contacts in publishing?” Cap asks, offended. “You do realize I’m a corporate lawyer, right? I have my hands in all-the-fucking pots.”
Evan chuckles. “Yeah, well, I don’t want your dirty-fucking-hands anywhere near my baby sister.”
“I still don’t see why I can’t help little Miss Maybe out…” Cap grins a devilish smile. “I’m very accommodating.”
The mere idea of Cap and Maybe within 100 feet of each other makes my gut churn.
“Mr. Ives,” Clara’s voice chimes through the intercom. “Your nine-thirty is here.”
“All right, well, I’d like to say it was great talking to you bastards, but I prefer not to start off my Monday with lies.”
Evan smirks. “Thanks again for helping Maybe out.”
“Of course. No problem.”
“And what about me?” Cap asks, and I laugh.
“What about you?”
“Don’t I get a thank you? A lunch date? Some-fucking-thing for all of the hard work I’ve put in for you dicks?”
“Aw, you feeling left out, bud?” I ask in a sugary voice. “How about I take you out to lunch next week? Will that make you feel better?”
His pout turns serious. “Somewhere nice?”
“Don’t worry, sweetheart. I know you’re a five-star restaurant kind of lady.”
“As long as we’re on the same page,” he retorts, and I click end on the call before he can rope me into another ten minutes of ridiculousness.
But in typical Cap fashion, before I even have the chance to let my nine-thirty appointment into my office, he insists on having additional last words via text.
Cap: Why don’t you go ahead and bring Maybe along? I’d love to meet this off-limits sister of Evan’s…
I roll my eyes. Always the shit stirrer.
Me: Lunch is canceled on account of you being a dirty bastard.
Sadly, my message doesn’t give me the satisfaction it should. If anything, it’s a stark reminder of the way I’ve been thinking about a very grown-up Maybe since the first time I saw her.
If anyone’s a dirty bastard, it’s me.
Maybe
After a short ride on the E train to SoHo and a five-block walk through a quiet side street of unique storefronts, I spot the sign for Charlie Bird—a cool, new-American eatery that Lena chose.
I locate her quickly, seated at an outdoor table with a half-drunk glass of white wine sitting in front of her. I nod my direction at the hostess and head straight for my delightfully weird new friend.
“Looks like you already got started without me,” I say by way of greeting and sit down in the seat across from hers. “I hope you weren’t waiting too long. There was a delay on the E.”
“Not at all.” She shakes her head. “You’re just on time.”
Just on time? Pretty sure I’m fifteen minutes late, but who am I to argue?
I order a coffee from a fauxhawk-sporting, emerald-eyed server named Grady, and Lena frowns in disappointment.
“Really?” she questions. “Coffee? You’re not going to have something fun with me?”
“Trust me, I’m three cups behind my usual four-cup quota for the day. It will benefit both of us if I drink coffee.”
She laughs, shakes her head, and sips her wine while we both peruse the menu. It feels weird to have silence with a virtual stranger feel comfortable, but she’s so at ease with it, I can’t help but be the same.
By the time Grady comes back with my coffee, we’re both ready to order.
“Burger and fries, please,” I say and hand him my menu. “But I do have one very special request.”
Grady grins. “Hit me with it.”
I loathe coming across as difficult, especially when I’m at a restaurant, but this is one thing I can’t help but be difficult on.
“Please keep any and all onions away from my plate,” I say in the nicest way possible. “I’m truly not trying to be a pain in the ass here, but I’ll literally puke if they accidentally end up in my food.”
“Got it,” he says with a soft smile. “No onions.”
“I am forever grateful.”
Once Lena orders and the waiter heads toward the kitchen, she flashes a secret grin my way.
“You are flipping adorable.”
I furrow my brow. “What ar
e you talking about?”
“Trust me, even our server would agree with me on this. You’re adorable.”
I groan and scrunch up my nose. Adorable is the last thing I want to be. Gorgeous, sexy—even hot. Now those are adjectives I can get behind.
“What’s wrong with adorable?”
“Adorable is for puppies and kittens. I want to be seen as a grown woman.”
“There’s nothing wrong with adorable.” She grins and takes a sip of wine. “Trust me, honey. Adorable for a grown woman is good. Guys blow their loads over adorable.”
I snort. “They do not.”
“Oh yes, they do.” She nods. Eyes serious. “Being able to combine innocence and secret sexpot is dick kryptonite.”
“Secret sexpot?” I question on a laugh.
“I have a good eye for these things.” Her smirk is both knowing and devilish. “I can tell, beneath those cute little jean shorts and Converse and beautiful girl-next-door face, there’s a total freak just waiting to come out.”
I don’t know how to respond to that. At all. But I don’t need to because Lena is apparently well-versed in the art of keeping conversations going all by herself.
“Trust me, our server Grady is probably in the back adjusting his boner for your adorableness as we speak.”
A shocked laugh escapes my throat. “He is not!”
“He totally is.” She laughs again. “Just stick with me, and I will enlighten you on all things men.”
With her long blond hair and bohemian dress and hippie-chic vibe, Lena is the epitome of confident goddess. She is the sun, and cool girl vibes are her rays of light, radiating from her every action and word.
No doubt, I could certainly use her wisdom when it comes to men.
“So, you just moved back to the city and you’re on the job hunt?”
I nod.
“Did you grow up here?”
“Yep. My family owns a floral shop in Chelsea.” I nod, pouring two sugar packets and a bit of cream into my coffee and stirring it with a spoon. I finish stirring and take a sip of coffee to test it out. “What about you? Have you always lived in New York?”
She nods. “Born here. I’ll suffer through life here. And no doubt, I’ll die here.”