The What If Guy

by Lauren Blakely

  I let the thought marinate for a moment, stirring it around, wondering how it’ll taste, before I say, “I like Bryn. A lot. At first, when I saw the site numbers for the piece, I thought wanting to see her was because of the article. But then I realized it’s not that at all. I don’t care if she writes about me or us or the app again. I like her. I want to date her, plain and simple. I want to know how to do this the right way. Is it against the rules, or does it just require disclosure if I date her?”

  He strokes his chin, switching instantly to full-on legal mode. “You’d have to disclose it to HR. You shouldn’t be dating a direct report, and if you are, you’d need to discuss with HR about having her moved to a different manager. You’re the CEO, so you don’t technically need her reporting to you, and you’re not even going to be in the same office much after this week, but you still need to do this the right way.” He begins to rattle off options. “You could, for instance, add in layers of executive or senior VPs between you and the other VPs. Or you could have her report to your COO. That’s a reasonable solution, and it’s better, frankly, than sneaking around.”

  The wheels in my brain turn faster, picking up speed. Sure, it’s only been a few days, but I’m so damn drawn to Bryn that I want to see what’s there. “Should I do that? Is that crazy?”

  Smirking, Oliver taps his chest. “You’re asking the guy who engineered a fake fiancée-ship with his best friend so as not to lose a client. I’m hardly the best one to give advice on this. But I can tell you this for sure—talk to her first.”

  I noodle on his advice all day and into the next, weighing it, considering it from all angles.

  And forty-eight hours later, I still feel the same way.

  I text Bryn and ask if she can meet me after work that afternoon to discuss a business matter.

  This is business after all.

  I’m not nervous. I’m not nervous. I’m not nervous.

  Hell, I don’t get nervous.

  My plan is to be straightforward with Bryn the second she walks into Dr. Insomnia’s Tea and Coffee Emporium. It’s on the Upper West Side, and I know Bryn lives in the Village, but I didn’t want to meet her near work.

  At six on the dot, she enters.

  And I’m a little nervous now.

  But I’m also certain. Forget “Mr. Smolder.” Forget the numbers. The numbers just illuminated what I’ve learned this week. I want to give this a shot. I hope she wants to as well.

  Bryn walks over to me. She’s still in her work clothes—a green skirt and a black blouse.

  It’s no surprise that she looks stunning. But there’s more at play than mere looks. All our conversations over the last week have stoked my desire to see what we might find between us.

  When she reaches me in the back of the shop, I stand and brush a kiss on her cheek before I realize what I’ve done. “Shit, sorry.”

  With a curious smile, she asks, “Why?”

  “I’m trying to be professional,” I say, gesturing to a chair.

  “How’s that working out for you?”

  I run a hand over my hair, laughing lightly. “Terribly. Can I get you something?”

  “Sure. A latte would be great,” she says.

  I head to the counter and order two, glancing back at her. She’s fiddling with some bracelets and glancing around. I wince. I’m so damn new to this—this modern dating thing. I should have told her why I wanted to see her.

  When I return, I slide her the mug. “Your non-mojito.”

  “Thanks,” she says, then takes a sip. “It’s a delicious non-cocktail.”

  I take a drink of mine, then rip off the Band-Aid. “Listen, I should have said why I wanted to meet with you.”

  “It’s because ‘Mr. Smolder’ did so well, right? You want to keep it up?”

  I blink. “What? Well, yes, it did. Advertisers love it. I love it, and it raises some questions.”

  “No one knows it’s about you and me. I told you that,” she says, her tone a little defensive, her eyes a little scared. “But if advertisers are pressuring you to run another piece, we should definitely talk about it.”

  “That’s not why I wanted to meet you, Bryn. This isn’t about the piece. Well, in some ways it is,” I say.

  Her brow knits.

  I try again, pushing up my sleeves and looking down at my ink, drawing strength from it. “When my marriage ended, I was in a pretty bad place. I saw the world negatively. I was pissed and angry, and just generally believed everything in life had gone to hell.”

  “It’s understandable to have been mad.”

  I run my thumb across the lotus flowers on my skin. “But I didn’t want to be mad forever. And I’d always wanted to get a tattoo, so it seemed like the right time, when I was trying to figure out how to go from being this married guy with a kid to this divorced guy with a kid. I got this lotus—for change. So I could try to live my life on the other side. And part of that is honesty.” I draw a deep breath, meeting her gaze. In her eyes I see patience, and it’s wonderful. It’s refreshing.

  “And the thing is, even though we haven’t done anything . . .” I stop to sketch air quotes, and she laughs, then we both turn more serious. “I feel like I’m not setting a good example. I’m a week and a half into being the new CEO of The Dating Pool, and nearly every day I flirt with you, text with you, talk to you, or think about doing those things.”

  She nibbles on the corner of her lips, nodding, a guilty look in her eyes too. “Same here. I feel like I’m a bad leader. The writers and editors wanted to know when I was going to write about my second date with you. They asked me that the other day.”

  The idea of another date with Bryn makes my heart thunder and my skin sizzle. And it makes my brain happy.

  But there are hoops to jump through. Things to consider and choices to make.

  “I talked to Oliver this week,” I continue. “He’s my best friend from way back, and he’s also my attorney.”

  She pulls a face. A confused face. “Are you asking me to sign something?”

  “No, no, God no,” I say, laughing then stopping.

  She exhales, relieved. “Good. Because it sounded like you were going to ask me to sign an NDA.”

  “No. Sort of the opposite,” I say, girding myself for her reaction. “Here’s the thing. It’s not necessarily a good idea for the CEO to date employees, but it is possible. And since we dated before, and met before, and talked before, I think we can pull it off if we disclose it to HR. If we’re on the up-and-up.”

  Her gorgeous green eyes widen. “We’d have to tell everyone?”

  “Essentially, yes.” I try to read her. I’m dying to know if she’ll seriously consider my offer.

  Her voice is heavy as she asks, “All the writers, editors, and designers who work for me would have to know?”

  A weight sinks in my gut as reality registers fully.

  While this might seem like an easy solution to me, since I’m in charge and I don’t really know any of them yet, it’s an incredibly difficult choice for the woman across from me.

  She’s the one who has to absorb the brunt of any blowback.

  18

  Bryn

  As I look at Logan across from me, his hands on his mug, his brown eyes locked on mine, I see a man who’s putting himself out there. Who’s laying his feelings on the line.

  My heart wants to reciprocate.

  But my head doesn’t know how to be me and do this. To be the person I’ve fashioned myself into—a leader, a lady boss, a stand-up citizen at work.

  I need to try though. He deserves that much, and so do I. He’s not asking me to do this for the “Mr. Smolder” series to continue. He is asking me to do this because he cares for me.

  That makes a huge difference.

  But the thing is . . .

  “It’s not that I don’t want to do that,” I say, but then backpedal because a double negative isn’t the way to go. “I want that, Logan. I do. Please know I do.”

>   A tiny smile curves his lips. “Good.” It comes out as a relieved whisper.

  I swallow past the stone in my throat. “But it changes a lot for me.”

  His eyes are serious, intense, and he nods, getting it. “I know. I completely understand that this is more of a risk for you to take on than it is for me.”

  “And there’s Isaac.” I picture the man I discuss baseball with. Only baseball. “Isaac is great, but he and I only ever talk about the Yankees. And I like it that way. I like debating the team’s chances with him. I like that I don’t have to go to him with trouble. I like not discussing my love life with him.” I take another drink, needing a moment to sort through the tangled skein of issues I’d face. “And sure, on the one hand, I run a site where discussing our love lives is par for the course. It’s the very reason for the site. But I prefer doing that when said love life is with someone who’s not involved with signing the checks.”

  He’s stoic, but I can see a hint of sadness in his eyes, like I’ve just sucker-punched him. Maybe I have, though it’s the bare truth. I never intended to tango with my boss. Don’t mix business with pleasure. That’s one of my mantras. One of my mother’s too.

  But that look on his face tugs on my heart. Makes me want to say yes. His honesty, his forthrightness, they make me want to loop my arms around his neck and smother him with kisses then ask him to take me home.

  Trouble is, I don’t know how to balance these warring wishes. “I’ve worked hard to keep my personal life separate from business. I don’t date people I work with. I want to inspire the people I work with. I want to elevate them. Help them be the best. I don’t want to be a source of office gossip, though, and I keep thinking I will be if we’re together. It’s like my mom always said: Don’t give them something to talk about.”

  “The opposite of the Bonnie Raitt anthem,” he says wryly.

  “Exactly. I try to do the opposite.” I reach for his hand, wanting to take it, but knowing I can’t yet. Because I don’t know if I can do this. Flirting in the office was risky enough, but this—his offer—is the real line. This is the public line.

  I place my hands in my lap.

  “But I’m not saying no. I’m saying”—I draw a deep breath—“I’d like to think about it this weekend.”

  “Of course.”

  The speed of his answer, the certainty behind it is one more reason why I’ll be giving it so much thought.

  Later that night, as I sink onto the bed next to Bruce, I bury my face in my hands. How can I date my boss when one wrong move could mean losing everything I’ve worked for?

  The answer is simple.

  I can’t.

  But is that the answer I’ll give?

  19

  Bruce

  Day 897 in Prison

  * * *

  What?

  Who was disturbing his slumber?

  Bruce had been training hard to sleep twenty-two hours a day. He’d surpassed twenty-one the other month and had closed in on twenty-two a few weeks ago.

  He was enticingly near to making that mark today.

  He barely bothered to open one eye, doing so only because he needed to know the enemy.

  Ah, the woman.

  The jailer.

  The human he tried to resist.

  She’d flopped down next to him on his bed. She liked to call it her bed, but he knew whose it truly was. His. The entire expanse of soft blankets and warm pillows belonged to him.

  He’d commandeered it months ago, his first act of jailhouse rebellion, claiming it as his own, rubbing his body against it, leaving fur where he could.

  Marking it all over.

  “Bruce,” the woman said with a sigh, sliding a hand along his spine.

  Ah, that was sort of . . . pleasant. Her hand felt exceptionally good.

  “What am I going to do?”

  Bruce hoped she’d pet him. She’d vastly improved her petting skills over all these long days of incarceration. She used to pet his belly, and he’d taught her quickly, with a few well-placed nicks and scratches, NEVER TO DO THAT AGAIN.

  Fast learner, she now only stroked his back.

  Purr-fection.

  “He wants to tell HR. To be open. To try dating. And I want that. Truly, I do. But what if . . .”

  What if she stopped stroking him? That would sadden Bruce immensely, so he amplified his noise-making device, using it to encourage her to keep it up.

  Petting like this would put him back to sleep, and sleep was what he craved most.

  Well, after trout.

  And flounder.

  And, admittedly, a grilled branzino. His mouth watered as he remembered the one she’d given him a few weeks ago. That was when he’d first started to curl up with her at night. After all, branzinos were branzinos, and he’d wanted her to know he’d appreciated the gift of adoration laid at his paws.

  “What if it all comes back to haunt me?” she continued with a heavy sigh. “If it doesn’t work out, I’m just the woman who dated the CEO. Who slept with the boss. And he’s still . . . the boss. Nothing changes for him. It’s harder for women, you know.”

  It’s harder for cats who can’t catch branzinos on their own. That was what was hard. Try not having access to a stream for fishing. Talk about misery.

  She chattered on as she stroked his fur. “I told him I need to think about it. Maybe over the weekend. Because what if it goes south like everything did with Evan? That can happen, right?”

  Evan. The word sounded so familiar.

  Ah, Evan. That name she’d used for the wretched man she’d once lived with. That man, if Bruce recalled correctly, had been jealous of him. That Bruce was far more beautiful than any human could ever be was reason enough, but also, the woman liked Bruce, and Evan was jealous of a cat.

  Well, that only made him smart. He should be jealous of a cat.

  But Evan had never given Bruce a branzino. Bruce’s stomach convulsed at the memory of his long-ago jailer, of Evan’s selfishness in keeping branzinos only for himself.

  Bruce leapt up, hacked several times, then proceeded to vomit up his dinner.

  All over the covers.

  There. That’d show her what he thought of Evan. That would answer her question.

  “Oh, Bruce. You poor thing. I hope you feel better soon. Let me change the bedding.” As she cleaned up his sick, she sighed. “That’s obviously a sign that it could all go wrong. Relationships always do, don’t they?”

  Bruce climbed up on the windowsill and licked his paw. Then, because he’d once seen her laugh when she watched a cat do this, he swatted a mug off the sill.

  Crash.

  The mug broke. Yes, that was satisfying too.

  “Oh, brilliant!”

  She snapped a photo of the carnage, stroked his back, and scratched his ears. She did seem pleased with him, and that was, he had to admit, growing more appealing by the day.

  20

  Bryn

  On Thursday I have meetings all day with our content partners.

  As I zip around town, I think.

  As I dart into meetings, I contemplate.

  As I march down the sidewalk, I wonder.

  The whole time I dip into the big ol’ bag of advice my mom left behind, fishing around for that one perfect bit of wisdom.

  But I’m not sure which one to clutch, the go for it adage or the do the right thing motto.

  I spend Friday prepping for my trip to California next week. After work, I meet with Teagan at Peace of Cake. Our friend Amy comes too, because she loves us and because she can’t resist cake.

  After I order a slice of coconut cake to share, Amy plops into a chair, red glasses on, and gestures grandly to me. “You have called me to a cake meeting. I can only presume you have a big dilemma.”

  “Yes. I put it before the cat, and he gave me contradictory advice,” I say as Amy digs in.

  “Huh. How odd for a cat to be contrary,” Teagan says drolly.

  “Shocking, I
know.”

  “So, what’s the dealio?” Amy asks.

  I spread my hands on the table, leaning on the scale I use for bad decisions. “On a scale of one to a box of rocks, how dumb is it to date the guy who just bought the site I work for?”

  Amy flinches, her fork freezing in midair.

  My shoulders sag. “I’ll take that as a vote for a truck full of rocks. A quarry full of stone.”

  Teagan clears her throat and points at me. “In Bryn’s defense, she was dating him before he bought the site.”

  “Well, before either of us knew who the other one was,” I clarify.

  Amy blinks. “Back it up, ladies, and explain. Don’t leave out any juicy details.”

  I unspool the tale, especially what weighs on me the most. “I love my employees. I love Matthew and Rosario, Quentin and James. And I can’t help but wonder how they’ll view me if they know I’m sleeping with the guy in charge.” I fiddle with my bracelets. “Will they see me as less of a lady boss? As more foolish? Will I seem less strong, less kick-ass? I want to be this badass woman who knows her mind. Who goes after what she wants. Like my mom was,” I say, and I don’t choke up. I stay strong. Because that’s who she was. That’s what she taught me to do, how to be.

  Teagan squeezes my hand. “You are strong. You’re so much like her in the ways that matter, sweetie.”

  “But what if the people I work with don’t see me that way?” I ask softly. That’s the big issue. My job matters to me. My identity matters. I care deeply for the staff at the site.

  Amy taps her chin thoughtfully. “It’s hard, I know, because you want them to respect you.”

  “And sometimes, call me crazy, but people can be judgy of women,” Teagan puts in.

  “Yeah. Just a little bit. So I don’t know if the answer is easy.”

  “It’s not easy,” Teagan says, eyes locked with mine.

  “It’s a choice,” Amy adds, setting down her fork, holding that same serious tone.