The Rom Con(38)

Christine smacks his arm but Jack only laughs, clearly used to having this conversation. “Fine, the connections part is useful, I’ll give you that.”

“And the access to every major sporting event,” Greg points out.

“And that.”

“And the personal friendships with the greatest athletes in the world.”

“Fine, those too,” he concedes with a grin. “But there’s also unflattering media attention, constant lawsuits, employee headaches, a perpetually dissatisfied board of directors that complicates every decision we try to make . . . trust me, it’s not all Super Bowls and Stanley Cups.”

I can’t help myself. “Come on, you don’t get to complain about negative media attention when you’re the ones courting controversy.”

“Ah, there she is! That fiery, slightly unhinged woman who told me off at a bar.” Jack’s eyes spark as they fix on me. “I wondered where she’s been hiding.”

Crap. I realize my mistake the second my brain catches up with my mouth: I’ve broken character again. Betty would never talk back to her man. But hot damn, staying silent and submissive is so much harder than it looks.

“She’s been here the whole time,” I say eventually, meeting his gaze head-on.

“Has she, though?” His dark eyes are lit in challenge and I’m reminded that he likes this push-pull dynamic between us; he enjoys being provoked. The site is called Brawler, after all.

So I give him what he wants: a heaping dose of Cassidy. “She has. Guess I just didn’t expect you to play the ‘poor little rich boy’ card. Not sure it suits you.”

I keep my tone playful, careful to ensure I can pass off the dig as flirty banter. He doesn’t flinch—not visibly, anyway—but when I look closer, I see a shadow reflected in his eyes, and for one blink-and-you’ll-miss-it moment, I think I’ve scored a direct hit. Strangely, the knowledge doesn’t give me the satisfaction I thought it would.

Before he can respond, our server, a young guy with a man bun, returns with my wine and sets it down in front of me. “Are you all ready to order, or would you like more time?” When Greg answers in the affirmative, my stomach tightens at what I know I have to do next.

I reach over and rest my hand lightly on Jack’s forearm. “Would you mind ordering for me?”

He blinks at me once. Twice. “Order for you?”

“You’ve been here before, right? I’m sure you know what’s best.” I smile guilelessly.

His eyes flick to our waiter, currently busy with Christine and Greg, then back to me. “Are you . . . sure?”

“I’m sure I’ll like whatever you like.” I sound like the queen-to-be in Coming to America.

“Uh . . . okay,” he stammers after a beat, then reaches for his discarded menu, knocking over a saltshaker in the process. He’s delightfully rattled. “How hungry are you?”

I shrug airily, helping him exactly zero percent. “So-so.”

When it comes to the 125 tips, the rules for dining are actually wildly inconsistent. One says to Order a steak rare, while another espouses the “cabbage soup diet” as the secret to a trim waistline. Choose the most expensive thing on the menu, but Show him you can have fun on a cheap date! Experiment with meals that have the spirit of adventure, but also Cook him foods that are basic and familiar, like his mother made. (I’m deliberately ignoring the tips that veer into fat-shaming: Go on a diet if you need to, or If your mother is plump, tell him you take after your father. If he’s fat too, tell him you’re adopted!)

Rather than try to parse through that contradictory advice, I made a pregame decision to place the ball squarely in Jack’s court, giving him a golden opportunity to mansplain the menu while assuming the presumptuous, male-dominant role he was born to occupy. It’s a twofer.

But Jack bypassing my carefully laid bait seems to be becoming a theme. “Do you eat meat? Or are you more of a salad person?” He’s trying valiantly to pass this ridiculous retro test, but he’s definitely sweating.

“Surprise me. I trust your judgment,” I reply magnanimously, giving him absolutely no guidance whatsoever. It’s a challenge to keep a straight face, but I’m nothing if not committed.

Our waiter clears his throat expectantly, pen poised over his notepad. A faint pink hue’s started to bloom up the back of Jack’s neck, broadcasting his discomfort. It’s such a treat to see him squirm.

“She eats meat,” Greg offers helpfully, and I howl internally. “And you can’t go wrong with the crab cakes, she loves those.”

Damnit, Greg! I can’t decide whether to strangle him or thank him (since I did, in fact, want the crab cakes), but seriously—can’t anything go the way I need it to? I want to stomp my feet under the table like a tantruming toddler.

As soon as the server leaves, Jack makes quick work of shucking his jacket (I was right; totally sweating), then takes a long pull from the old-fashioned. “You caught me off guard there,” he admits in a low voice, setting his drink back down.

“What do you mean?” I am all puppy-eyed innocence.

“You don’t seem like the type of woman who’d want a man ordering for her.”

“That’s because she’s not,” Greg says flatly. He jerks abruptly and I’d bet money Christine just kicked him under the table.