Was that too easy? “Anything, really. Tell me something I don’t know about you. Actually no, wait. You said you’ve never done a dating app before, right? Let’s pretend we’re setting up your profile. Give me the full rundown: likes and dislikes, favorite food, favorite place to travel, whatever. I want the ‘Jack in a nutshell’ executive summary.”
His cheeks go a little pink, and it’s then I realize just how unused to the spotlight he really is. “Jack in a nutshell, let’s see. I was born and raised in New York, so clearly I’m a bit of a homebody. I have to stay on top of basically every sport for work, but I really only like playing golf and going for runs. I couldn’t possibly pick a favorite song. My mom made us learn the piano as kids even though I would’ve rather played the drums, but she couldn’t handle the noise. Oh, when I was in middle school I tried out frosted tips. It wasn’t a good look for me.”
“Or anyone,” I quip.
He bobs his head in agreement. “My favorite subject was history, and I love doing nerdy stuff like touring historic sites or presidents’ homes. I get excited about data and metrics. I get cranky if I don’t get enough sleep. I have a temper, especially when people disappoint me. I have a red tie I wear when I want to feel intimidating. I love ketchup and spaghetti sauce but hate tomatoes. If I could eat anything it’d be Italian, specifically the chicken parm from this amazing hole-in-the-wall restaurant in Little Italy I stumbled across years ago. I’ll have to take you.” His eyes flick to mine, a little shyly, and he clears his throat. “I also love a good hotel continental breakfast. I don’t really have a sweet tooth. If I could vacation anywhere, it would probably be Greece.” He finally breaks for a breath. “How’d I do?”
“Not bad. I’d probably swipe right on you. Extra points for not mentioning hiking, CrossFit, or craft beer.”
He laughs out loud, and we grin at each other while Doris Troy croons in the background about falling so hard, hard, haaaard in love, the music filtering through the room at just the right volume. A feng shui expert was paid thousands to determine this exact decibel level. It’s romantic as hell.
I tuck a knee beneath me and watch his eyes slowly trail over the exposed skin of my thigh, and his expression is . . . well, I can only describe it as longing. I decide to do something quite cruel and shift slightly, making my hemline ride up even farther, and now he’s the one shifting in his seat, leaning over to grab his wineglass and tossing back its contents in a single swift gulp.
I decide to take advantage of the mood and his candor and press my luck with the next question—though I admit, it has nothing to do with the story. This one’s all for me. “Still an open book?”
Apprehension darts across his face. “Sure.”
“I’d love to hear more about your family. You’ve made some comments about them that have me a bit curious.”
“Ah.” He blinks a couple of times before breaking my gaze, his eyes flicking back to the game board. “I think I’m going to need some more liquid courage before I answer that one.”
He gets up to go to the kitchen, and when he comes back, he’s got the wine bottle in one hand and a crystal tumbler half-full of amber liquor in the other, one large spherical ice cube floating in the glass. He even has fancy ice.
“Switched to the hard stuff, huh?”
“This story requires something stronger,” he says as he refills my wineglass, and once he’s resettled on the couch, he begins. “So, my family. Not necessarily my favorite topic, because honestly, they would scare off any sane woman.” He eyeballs me, gauging my reaction, as though I might bolt off the couch and make a break for it right this very second.
“Is your dad actually Charles Manson?”
He smiles briefly. “No.”
“Part of a notorious crime family?”
“Not that I’m aware of.”
I wave a hand dismissively. “Eh, serial killers and mob bosses are my only real deal-breakers.”
“A low bar, that’s good.” He clears his throat. “So, my mom and dad were introduced by mutual friends after college and dated for a year or so before getting married. Their families both ran in the same social circles, so it was considered a good match. At that point my dad was working at an investment bank and my mom was in fashion, though she quit when my brother was born.” He pauses. “They named him John Jr. and me Jack, if that gives you any indication of my father’s ego.”
“If it makes you feel any better, my parents named us Colin, Christine, and Cassidy. The triple C’s are about as nineties as you can get.”
He laughs wryly. “Since you’ve googled me,” he says, making it sound like a dirty word, “then I’m sure you’ve read about my dad. He’s obsessed with money: making it, spending it. He also uses it as a weapon by withholding it when he sees fit. He’s ruthless and manipulative, and once I was old enough to figure that out, I did whatever I could to stay out of his way. He enjoys wielding his power and influence over everyone, including his family. Especially his family.” He pauses. “He’s also a serial philanderer, which you probably didn’t read about.”
My jaw drops. “Oh, geez. Jack, I’m sorry. You know what? Forget I asked about this. It’s none of my business.”
He waves away my objections. “No, you should know what you’re getting yourself into. My family is . . . not the Cleavers. More like the Bluths. Only more dysfunctional.”
“Is your mom—I mean, how does she . . .”
“How does she feel about being repeatedly cheated on?” He lets out a humorless laugh. “When we were young, they would get into these crazy fights. Screaming matches and blowups, and then she’d give him the silent treatment for a few days. Eventually things would go back to normal, and then the cycle would repeat itself. By the time I was a teenager, she was self-medicating as a way to deal with it.” He looks pained. “I know she did the best she could for us under the circumstances, and she didn’t deserve the way my dad treated her, but she also refused to leave him, which never made sense to me. It’s like she made a decision that she was going to look the other way, that she’d rather live a lie than blow up her life, and it didn’t matter if we were all miserable as a result.” He blows out a breath. “It’s taken me a long time to stop resenting her for it.”
Whoa. He takes a heavy swallow of his drink and I see now why he wanted the extra fortification. “What about your brother?”
He makes a low noise in the back of his throat. “Our relationship is . . . complicated. My dad would pit us against each other, encourage us to be competitive. You don’t always understand that when you’re young, and by the time we caught on to it, the die had been cast. And then when Brawler started taking off, I thought it would be a great idea to bring him into the fold. It seemed like a perfect solution—I could surround myself with people I trusted and fix our relationship. What could go wrong?”
This story is starting to make me sick to my stomach. “Oh no.”
“Exactly. Here’s a tip if you ever start your own business: Don’t hire your friends and family. It will blow up in your face.”