“Dr. Cute Guy?” he says seriously.
“Oh, shut up. I don’t know, Dr. . . . Smith?” I toss out uselessly. Pathetic.
“Wrong, but you’re actually not too far off. It’s Dr. Schiff.”
I throw up my hands, huffing in frustration. Jack smirks and takes his turn to roll while I grab a card.
“Okay, yellow. Your question is: Where did Chandler claim to be moving so he wouldn’t have to get back together with Janice?” I slam the card down on the coffee table. “Are you kidding me with this? That’s so easy! Did you rig these?”
“Yemen,” Jack says immediately, grabbing a yellow wedge for his cheese wheel.
“These are stupid, unfair questions,” I grumble as he goes to roll again.
“Hey, don’t blame the questions,” Jack mimics in a spot-on Ross impression, and I laugh in spite of myself.
Our back-and-forth continues in this vein, and I succeed in learning something new about Jack: He’s a competitive trash talker. Not exactly useful for my article, but entertaining all the same. He also knows way more Friends trivia than I thought he would. I have the edge, but it ain’t by much. Once it becomes clear that I’ll be coming out the victor （to my relief and his chagrin）， I prepare to make my move.
I select a card and pretend to read. “What is Jack Bradford’s biggest regret?”
His brows draw together. “That can’t possibly be what it says.”
I exhale loudly and flick the card at him like a Frisbee. “I’m ready for some Jack trivia,” I tell him, and he makes a face. “What? I feel like you know all this stuff about me—heck, you’ve already met my family—and I only know superficial things about you. I’ve learned more from Google than the horse’s mouth.”
He looks disturbed. “Please do not google me.”
“Fine, I won’t . . . again.”
He groans and lets his head fall back against the couch.
“I don’t know what you’re so worried about, it’s not like there’s anything to find. Anything real, anyway.”
He peeks one eye open, lolling his head toward me.
“Come on, spill it. Every time I ask you a personal question, you . . . well, you pivot.” I smirk and lean over to grab my glass of wine from the coffee table.
“Do I? I don’t mean to. I guess I’ve spent so long trying to protect my privacy and stay out of the news that I don’t always realize when it’s doing more harm than good.” He sits up and rolls his shoulders, like a runner limbering up. “I’m an open book. For you, at least.” He flashes me an easygoing grin and I feel that familiar pang again: guilt. “What do you want to know?”
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.”