Chapter 5
Chapter Five
Hailey
When You Try to Cross-Check Fate
The sun in Santorini is aggressively bright for a morning that already feels like a bad decision. I should just go back to bed.
Not a life-altering, ruin-everything mistake—let’s not be dramatic—but more of an ugh, did I really need that fifth glass of wine? kind of mistake. And, yes, the tequila shots were overkill.
I push my sunglasses higher on my nose, squinting at my phone with one eye open because committing to two feels like asking too much of myself right now.
A text from Leif sits at the top of my notifications. Time check: Have you embarrassed yourself yet today?
I snort and type back, The day is young, my friend. I have so much potential.
A waiter passes, trailing the scent of fresh coffee and regret. I groan, sinking further into my chair. “God, I need caffeine and a do-over on last night.”
Across from me, Aspen—who is either one of my closest friends or the reason I make questionable life choices, depending on the day—raises a brow over the rim of her espresso. “That bad?”
I peel my sunglasses off, wincing as the sunlight spears through my already-fragile existence. “Let’s just say I’ve confirmed, yet again, that dating is not my sport.”
Aspen scoffs. “How tragic for the men of the world.”
I sigh, swirling the last bit of my iced coffee. “I tried, Aspen. I really fucking tried. I was perfectly charming. I laughed at his stories—even the one about his hedge fund job and how he thinks humanitarian work is ‘nice.’ I was patient when he ordered for me, like it was nineteen-fifty-two, and I was just an optional accessory to his meal.”
Aspen hums. “Ah. So, you ran?”
“Not immediately,” I say, lifting my index finger hoping she waits until I make my case. “I lasted a whole forty-five minutes before texting Leif to fake an emergency call.”
“Wow. Restraint.”
“I know, right?”
My phone buzzes again and not surprisingly, it’s Leif: How do you keep finding the worst men on every continent? Do you have an app for that? Is it Ghostr International—so they can disappear faster than your self-respect? Red Flags Around the World—so at least you see them coming? World’s Worst Mates—because soulmates are overrated?
I groan, but then laugh, my fingers already moving across the screen: It’s a talent, you know? Some people juggle flaming batons, others train squirrels to ride bikes. I make terrible dating choices.
Aspen eyes me over her coffee. “Leif? Why do I even ask, of course it’s him. You’re always texting with him and reaching out to him when you need him to save you—even if he’s on another continent. You’re ridiculous.”
I look up, and her expression is far too knowing.
“What?” I shrug. “He’s my emergency exit buddy. I do the same for him—well, I would if he dated.”
She leans back, stretching like a cat in the sun. “You ever think maybe he’s the reason you don’t actually try with any of these guys?”
I scoff. “Excuse me, I try very hard to be open to love. It’s just that love keeps showing up in the form of emotionally stunted finance bros with the self-awareness of a potato, or guys who think being open to a relationship means they want to date more than one woman at a time, or?—”
Aspen cuts me off with a pointed sip of her drink. “And yet, you and Leif have been talking every day for what, ten years?”
“Fifteen,” I correct, stabbing my spoon into my now-melted coffee. “That’s different. We’re best friends.”
“Right,” she says, unconvinced. “Ever thought about dating him?”
I laugh, leaning back in my chair. “Leif and I are—we’re different. He’s just there, you know? He’s like . . . I don’t know, the North Star or something.”
Aspen tilts her head. “Hailey, you move constantly. You’ve lived in seven different time zones in the last two years. If Leif is your North Star, then why are you still wandering?”
I open my mouth—then close it.
“Not that kind of North Star,” I say, but even I can hear how flat it sounds.
Because what am I supposed to say? That he’s the one person I don’t know how to mess this up with? That I’ve built my entire adult life around the idea of leaving before I get left, and Leif is the only person I can’t afford to risk?
No.
Instead, I change the subject. “So, do we think I’ll ever find a guy who isn’t a walking red flag?”
Aspen grins. “Probably not.”
“Great. Love that for me.” I drain the last of my drink and push my chair back. “Let’s finish breakfast and get to work. This might be paradise, but they don’t pay us to enjoy it.”
“They don’t pay us until we deliver,” she reminds me, arching a brow. “Are you sticking around after we wrap?”
I hesitate. “Probably. My choices are either heading back to New York to wait for a green light on one of my pitched documentaries or staying here and dodging my family.”
Not that anyone could blame me. At my grandmother’s birthday, the conversation was a relentless interrogation— When are you settling down? You’re too old. We —meaning my grandparents— will die before we meet our first great-grandchild. Even the General—who I sometimes, begrudgingly, call ‘Father’—had an opinion. Retirement must have given him extra time to meddle.
“If I had a budget for my next project, I’d bring you on,” she says, matter-of-fact.
“No worries.” I tilt my head, taking in the postcard-perfect view of Santorini—the whitewashed buildings stacked against the cliffside, the sun slipping lower over the Aegean, streaking the water in gold. Maybe staying here isn’t the worst idea.
* * *
And because I am nothing if not committed to my brand of questionable decision-making, I end the night in someone else’s bed.
Don’t judge. I haven’t had sex in . . . a long time. A very long time. Probably a year. Maybe more. This is the first time I don’t leave in the middle of a date because there’s no chemistry—or I’m annoyed as fuck. Listen, I’m not picky, I just don’t know how to choose the right guy. People joke about it, but it’s the truth. I am a terrible judge of character when it comes to men.
Aspen says it’s daddy issues. I try to give men the benefit of the doubt, but they always disappoint me and I just walk away. Except today. Listen, it seemed like a good idea at the time to sleep with him. Did tequila help with that decision? I’d rather not talk about it.
Don Julio and I need to have a serious conversation about boundaries.
I wake up to a regret headache and a text from Leif.
Leif: Are you alive?
I groan, rubbing my temple as I slide out of the bed that is not mine. The man—Mark? Mike? Something-M?—is still asleep, snoring lightly into his pillow, blissfully unaware that he is now part of my ever-growing list of Why Did I Do That? moments.
No, those moments don’t include one-night stands all the time. Most of the times are . . . well, other stuff I’d rather not disclose. I scan the floor, spot my dress next to a shoe that is absolutely not mine, and tiptoe through the room like a fugitive.
Once I’m safely outside, I text back, Barely. Also, tell me why I do this to myself.
He of course responds immediately: I assume this is either having a terrible date or . . . what did you do now?
I groan, wondering whether I should tell him what I really did. But why skip the issues when he practically knows everything about my dating life? And so I answer: A one-night stand, of course.
His response comes immediately, Oh, wow, a one-night stand? That’s something I would do, not you. Did you use protection?
I stare at the phone with my mouth agape. Is he kidding? Of course I did, I respond, very appalled by his question. Then add, That wasn’t my question. I asked why I did this shit to myself.
Leif: Oh, you want my professional opinion now?
Hailey: No, I want you to say something that makes me feel better about my life choices.
Leif: You’re a beautiful disaster with questionable taste. There’s your compliment.
I laugh, shaking my head as I head toward my hotel room. When I step into the elevator, I answer, That was mean.
Leif: That was accurate.
Hailey: Excuse you, I’ll have you know this guy was perfectly nice. He held doors open, didn’t talk about crypto, and had a full set of clean sheets. That’s an A+ in today’s dating scene.
Leif: Congratulations on your participation trophy.
Hailey: Rude.
Leif: So? What was wrong with him?
I sigh, swiping my keycard and entering my room.
Hailey: Nothing. I just wasn’t into it. He was nice but . . . I don’t know. He was too polite—even the sex was polite.
Leif: You like nice, well-mannered people.
Hailey: Yeah, but I don’t want to sleep with one. I need some bite. Some fire. Someone who doesn’t just agree with everything I say like I’m a customer service call.
Leif: This is interesting information. So, you need an asshole?
Hailey: Not an asshole. Just . . . someone who can challenge me a little. Maybe someone who takes charge, who is gentle sometimes, but also . . .
Leif: But also what?
I exhale, biting my lip before typing.
Hailey: Someone who doesn’t just follow my lead. I want him to control, to . . . dominate at times. Someone who isn’t afraid to push back. To thrust hard—very hard when I need it, and knows in fact that it is what I need. A guy who takes what he wants.
The response is instantaneous.
Leif: I had no idea you were . . . this is interesting. So, you like cuddles but also a little force, huh? So probably an asshole you can push around.
My stomach flips.
Hailey: I hate you.
Leif: Nah. You just don’t know what to do with someone who can handle you.
I stare at the screen, heart hammering, because the first person that comes to mind is . . . him.
He knows how to handle me. Always pushing back when I get reckless, cutting through my bullshit like no one else. But would he know how to fuck me? Would he take me apart with the same precision, the same unrelenting control?
I bet he would. And I bet he wouldn’t be gentle about it if that’s exactly what I needed.
He wouldn’t waste time with sweet words or careful touches. He’d shove me against the wall, grip my wrists, and hold me right where he wants me—fierce, demanding, making sure I feel every bit of his strength. I want him reckless with me, to leave marks I’ll feel for days, to take me until I’m wrecked and raw, pleasure curling into pain in the best way.
He’ll be ruthless. Fingers digging in, mouth biting down, voice dark with something that sends shivers down my spine. You can take it, can’t you? He’d push me past my limits just to hear me gasp, just to watch me tremble and break apart beneath him.
I’d run my mouth—because I always do—and he’d make me regret it. Not with words, but with his hands, his teeth, his cock, fucking me so hard I forget how to think. No teasing, no games, just raw, desperate need. A hunger so deep it leaves me shaking, aching, ruined.
I press my thighs together, exhaling slow, but it doesn’t help. Not when I’m all worked up and wanting. Not from Leif, of course. I wouldn’t ruin our friendship that way—never.
After a few deep breaths and calming down from a fantasy that I should never have texted him, Whatever. Anyway, what’s up with you? Please tell me you have better life news than I do.
Leif: I do, actually. It’s official.
I hold my breath as I type, Wait. Official, official? Weren’t we just discussing this yesterday or was it the day before yesterday? I lost track of time.
Leif: Actually, I took my sweet time. The New York Vipers wanted the response that same day we spoke—two days ago.
I let out a squeal so loud I’m pretty sure the entire hallway hears me. Then type, Fuck yes, Leif! NEW YORK! YOU’RE A VIPER!
Leif: Weird, that’s what they put on the contract, too. Kaden isn’t too happy—maybe Papa isn’t either. But the Barracudas didn’t offer me what I wanted. I wasn’t going to move to Boston with a pay cut and the need to show that I’m my father’s son.
Hailey: This is HUGE. Why didn’t you call me?!
Leif: Because you were out making bad choices.
Hailey: I don’t like you right now.
Leif: You like me. You’re just mad I couldn’t break the news between rounds of tequila.
Hailey: That would have been epic. You really missed an opportunity.
Leif: Next time I change teams, I’ll plan accordingly.
Hailey: Seriously, though, I’m so damn proud of you. I know you wanted out of Arizona, and back on the East Coast with a winning team.
Leif: Yeah. Feels weird, though.
Hailey: Because you have to leave Arizona?
Leif: Because I have to live close to my family. Plus, I might get to witness all of your terrible dating choices in real time now.
Hailey: It’s fine. I’ll just start making better ones now.
Leif: Oh, yeah? And how are you planning on doing that?
I stare at my phone, my smile fading just a little.
That’s the question, isn’t it?
Because if I knew the answer, I wouldn’t be sneaking out of some guy’s room at sunrise, wondering why I keep trying to find something that never feels right.
Instead of answering, I type back, Dunno. But you’re buying me a celebration dinner, and I will be getting three desserts.
Leif: I’d be disappointed if you didn’t.