The Rom Con(53)

“?‘There’s such a thing as too cocky,’?” he tosses over his shoulder, using my own words against me.

“So you watched a lot of Friends growing up?” I ask him, kicking off my kitten heels and getting comfortable on his couch—and holy moly, is this thing comfortable. It’s not cold or stiff like the leather couches I’m used to, but soft and supple and beautifully broken in. I sink into it like a cloud and suppress the urge to yawn. Whoever said money can’t buy happiness never met this couch.

“Actually, no. I probably caught an episode or two growing up, but I really hadn’t seen it much until college, when Tom got me into it. I guess his sisters were obsessed with it, so he always had it on, said it reminded him of home. Did you know he has three sisters?” He takes a seat next to me on the couch and starts pulling out the game pieces.

“He does?” I exclaim much too loudly, and Jack casts me a funny look. “I mean, no.”

How can a guy with three sisters be so crude and sexist? Make it make sense!

“Huh,” I comment blandly. I don’t get it. When it comes to Tom, I have more questions than answers.

Once we’ve picked our game pieces (Chandler’s vest for me, Monica’s turkey head for him) and gotten our cheese wedges ready, Jack hands me the dice.

“Ladies first,” he offers generously.

I roll the special dice and it lands on blue, which apparently corresponds to Seasons 7–8, and I shake out my neck. I’ve got this.

Jack draws a card. “In the episode where Rachel is pregnant and feeling ‘erotically charged,’ she goes to a doctor’s appointment and flirts with her OB-GYN. What is the doctor’s name?”

I blanch. “Are you serious? How is anyone supposed to know that? He was a minor side character! Does he even have a name?”

He smiles condescendingly. “Do you need to forfeit?”

Grr. “No. Um, let’s see, he had brown hair. I can picture him, that cute guy. It’s the Evander Holyfield episode.” Jack pointedly checks his watch. “Uh, Dr. . . .” I hem and haw, hoping for a lightning strike, but I’m coming up empty.

“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.”