Chapter 15
FIFTEEN
Max
The beer in my hand has gone warm, forgotten as Ryan recounts a story about some bar patron's disastrous attempt to impress a date. Drew laughs at all the right places, but I can barely focus, my mind circling back to the same uncomfortable thought: I'm in love with a woman I made a bet about not falling for. The irony would be hilarious if it didn't make me feel like complete garbage. It's been four days since our staged proposal at Brooklyn Bridge Park—four days of Lena wearing that ridiculous plastic ring on her right hand when we're alone, a private symbol that means more than the borrowed diamond that's setting Instagram on fire. Four days of knowing I need to tell her about the bet before someone else does, while simultaneously finding every excuse not to.
"Earth to Max," Ryan waves a hand in front of my face. "Did you hear anything I just said?"
"Something about a guy, a martini, and a regrettable fire hazard," I reply automatically, though I've processed none of the details.
Ryan narrows his eyes. "That was ten minutes ago. I've moved on to asking whether you're ready to admit defeat."
My stomach knots. "Defeat?"
"The bet," he clarifies, leaning back in his chair with a smugness that makes me want to throw my warm beer at him. "You know, the one where you swore you wouldn't catch feelings for Instagram Girl, and I said you absolutely would?"
Drew winces, clearly reading something in my expression. "Maybe we should drop it, man."
"Drop it? No way." Ryan sits forward, oblivious to the storm brewing inside me. "This is the sweetest victory. Mr. 'I'm Perfectly Capable of Keeping Things Professional' is thoroughly whipped. The evidence is all over social media."
"It's not like that," I mutter, though it's exactly like that.
"Oh please." Ryan pulls out his phone, scrolling through what I assume is Lena's Instagram. "The proposal photos? That look on your face? Either you deserve an Oscar, or you're in deep, my friend."
My hands are numb from gripping my beer bottle too tightly, but I feel a warmth in my chest, an uncomfortable heat that I recognize as guilt. The bet seemed so harmless three months ago—stupid male bravado between friends. One month's rent if I could fake-date Lena without developing feelings. Playing my guitar at Ryan's birthday party if I failed.
Back then, Lena was just a stranger with a business proposition. I couldn't have imagined how she'd infiltrate my life, how her laughter would become my favorite sound, how the smell of her shampoo on my pillow would make me feel more at home than I have in years. I couldn't have imagined the plastic ring still sitting in her jewelry box, waiting for a future proposal that might be real.
"The bet was a mistake," I say finally, setting down my beer with more force than necessary. "I want to cancel it."
Ryan's eyebrows shoot up. "Cancel it? You can't cancel a bet just because you're losing."
"I'm not canceling because I'm losing." My voice comes out sharper than intended. "I'm canceling because it was a shitty thing to make a bet about in the first place."
A silence falls over our usual hang-out spot—the living room of the apartment I share with Ryan, where Drew is a constant fixture. The three of us have been friends since college, through my band days, through breakups and career changes and everything in between. They know me better than almost anyone, which makes their failure to see how serious this is all the more frustrating.
Drew studies me, his expression shifting from confusion to concern. "What's really going on, Max? This isn't just about a stupid bet."
I run a hand through my hair, a gesture Lena often teases me about when I'm stressed. The thought of her makes my chest tighten further. "It's not fake anymore," I admit, the words feeling both treacherous and relieving. "Lena and I. We're actually together."
Ryan's eyes widen. "Wait, what? Since when?"
"A while now." I don't elaborate on the complicated progression—the night in my apartment during the rainstorm, the hallway at the charity gala, the confrontation with Sophie, the afternoon Lena finally admitted her feelings were real. It's too private, too precious to lay out for dissection.
"Holy shit," Drew murmurs. "Plot twist."
Ryan, for once, seems at a loss for words. He opens and closes his mouth a few times before asking, "Does she know about the bet?"
"No." The single word hangs between us, heavy with implication. "That's why I need to cancel it. I can't tell her I made a bet about not falling for her. It would hurt her, and she's been hurt enough."
"But if you don't tell her, and she finds out some other way..." Drew trails off, the conclusion obvious.
"I know." I stand, too restless to remain seated. "That's why it's keeping me up at night."
Ryan watches me pace, uncharacteristically serious. "You really care about her."
It's not a question, but I answer anyway. "Yeah. I do."
"Then you have to tell her," he says simply. “You owe her the truth. Come on, man. It was a harmless bet.”
But I’m not sure she’ll see it that way.
"And risk losing her?" The fear that's been gnawing at me finally surfaces. "She's been through enough bullshit with men using her for their own agenda. If I tell her I literally made a bet about her feelings?—"
"Then you're being honest," Drew interjects. "Which is what real relationships need."
"Easy for you to say. You don't have to see the look on her face when I tell her." I sink back onto the couch, suddenly exhausted. "I've been trying to find the right moment, the right words, but they don't exist. There's no good way to say 'Hey, by the way, I bet my roommate I wouldn't fall for you, but surprise, I'm in so deep I can't see straight.'"
Ryan's expression softens unexpectedly. "You love her, don't you?"
The question stops me cold. Love. It's a word I've been circling in my mind, testing and retreating from. A word that feels simultaneously too big and not big enough for what Lena has come to mean to me.
"I think I do," I admit, the confession leaving me vulnerable in a way I haven't been with my friends in years. "And that's what makes this so fucking terrifying. I finally find someone who sees me—really sees me—and I have this stupid bet hanging over everything."
"If she really sees you," Drew says quietly, "then she'll understand that the bet was before. Before you knew her. Before this was real."
"Or she'll see it as one more man who saw her as a means to an end. A challenge." I shake my head. "You don't understand what she's been through with her ex, with the industry she's in. Everyone wants something from her. Everyone has an angle."
"And what's your angle now?" Ryan asks, surprising me with his insight.
"I don't have one." The answer comes easily, truthfully. "I just want her. The real her, not the Instagram version. I want lazy Sunday mornings and arguments about ice cream flavors and watching her try to identify constellations even though she has no idea what they're supposed to look like."
Ryan and Drew exchange a look I can't quite interpret.
"What?" I demand.
"Nothing," Drew says with a small smile. "It's just…I've never heard you talk about anyone like this before. Not even Sophie, and you were with her for over a year."
"Lena's different." The simplicity of the statement belies the complexity of the feeling behind it.
"Then you owe her the truth," Ryan says, returning to his earlier point. "And for what it's worth, the bet is officially nullified as of now."
I eye him skeptically. "Just like that?"
"Just like that." He shrugs. "If it's real, it's not fair game for stupid bets."
"So no rent payment? No birthday performance?" The relief I expect doesn't come. If anything, the easy cancellation makes the bet seem all the more trivial, all the more shameful for having caused so much distress.
"Well," Ryan hedges, a glint returning to his eye, "I wouldn't object to a song or two at my party. For old times' sake, not because of any bet."
Despite everything, I find myself smiling. "You've been trying to get me to play again for over a year."
"Because you're good," he says simply. "And you love it, even if you won't admit it."
The observation hits closer to home than I expect. Since walking away from music, I've kept my guitars mostly as decoration, playing only in private moments when the urge becomes too strong to ignore. Lena has asked about it a few times, but I've always deflected, unwilling to excavate that particular wound.
"Maybe," is all I say. "But that's a conversation for another time."
"Fair enough." Ryan stands, grabbing fresh beers from the fridge and handing them around. "So what's your plan? When are you going to tell her?"
"I don't know," I admit. "We've got a Luminous Beauty campaign event next week. I don't want to drop this bombshell right before she has to perform professionally."
"After, then," Drew suggests. "Just rip the bandaid off."
I nod, though the thought makes my stomach churn. "After the event. I'll tell her everything."
"For what it's worth," Ryan says, uncharacteristically sincere, "I think you're overthinking this. From what I saw at the bar that night, the way she stood up for you with Sophie, she's not going to throw away something real over a stupid bet that predated your actual relationship."
His attempt at reassurance surprises me. "Since when are you the relationship guru?"
"I contain multitudes," he replies with a grin. "Besides, anyone can see you two are disgustingly into each other. It's nauseating, really."
"Thanks. Very supportive."
"Anytime." He clinks his beer bottle against mine. "And Max? For what it's worth, I'm happy for you. Even if it means you're going to be insufferably sappy for the foreseeable future."
The sentiment, delivered with Ryan's typical sardonic tone, nevertheless feels genuine. A lump forms in my throat, unexpected emotion welling up after weeks of stress and guilt.
"Thanks," I manage. "That actually means something, coming from a heartless cynic like you."
"Whoa, let's not get carried away with the emotional declarations," he protests, but there's no heat in it. "Save that for your Instagram girlfriend."
Drew watches this exchange with amusement. "This is touching and all, but are we actually going to watch the game, or just continue this bromantic heart-to-heart all evening?"
"The game," Ryan and I say in unison, both eager to retreat to safer conversational ground.
As Drew turns on the TV, Ryan catches my eye and gives me a brief nod—an unspoken acknowledgment of the significance of our conversation. Then, in a gesture so awkward and unlike him that it's almost comical, he reaches over and pulls me into a quick, back-slapping hug.
"It's gonna be fine," he mutters against my shoulder, clearly uncomfortable with the display of affection but pushing through anyway. "Just be honest with her."
The hug lasts approximately two seconds before he practically shoves me away, immediately pretending to be engrossed in the pregame commentary. Drew snickers at the display, earning himself a thrown couch pillow from Ryan.
As we settle in to watch the game, the weight on my chest feels slightly lighter. The bet is officially canceled, though the confession still looms. But Ryan's clumsy encouragement—so out of character yet so genuine—gives me hope that maybe, just maybe, Lena will understand too. That what started as something artificial has grown into something too real, too important to lose over a stupid wager made before I knew what I was gambling with.
I pull out my phone, looking at the most recent text from Lena: a photo of her desk covered in campaign materials, with the plastic ring visible on her finger as she gives a thumbs up. The caption reads:
Drowning in work but thinking of you.
The simple message, meant for no audience but me, reinforces my decision. I have to tell her the truth—all of it, even the ugly parts. Because what we've built, strange and backward as its foundation may be, is worth fighting for.
And if that means swallowing my pride, facing her potential anger, and yes, even playing at Ryan's birthday party as a self-imposed penance rather than a lost bet…well, that seems a small price to pay for the chance at something real.