“Well, it’s a big deal for us,” Christine continues. “We don’t get out much.”
“It’s your anniversary, you deserve to celebrate in style,” Jack says graciously, tapping his knife on his water glass in jest. “How many years?”
“Eight, but we’ve been together for twelve.” They moon at each other like horny honeymooners and I can’t help feeling a pang of envy.
I can barely remember a time when Christine and Greg weren’t together, which basically means I’ve idolized their relationship for a decade. They’re truly best friends—the embodiment of #couplegoals—as well-matched and secure in their relationship as Cory and Topanga. In fact, I blame them for giving me unrealistic expectations. Because of them, I always assumed I’d meet my soul mate in college and live happily ever after, too. Talk about a letdown.
“Your daughters are adorable,” Jack says as he unfurls his napkin. “Cassidy showed me some photos.”
“Meh, they’re alright,” Christine jokes. “They’re also—”
“Not here!” Greg finishes, and they high-five each other. At Jack’s confused expression, she clarifies. “We have a policy of not talking about our kids on date nights.”
Jack laughs at that. “Fair enough.”
Our server interrupts to take my drink order, and this time I wise up and request my usual pinot. Betty can bite me.
“Do you have any nieces or nephews, Jack?” Christine asks, sipping her martini.
He shakes his head. “No. It’s just my older brother and me, and he and his wife divorced before they had any kids.”
“Ah. Well, if you’re bored or hate sleeping, we have a couple we’re willing to lend you.”
Jack chuckles. “Sign me up.”
“So, how’d you two meet?” Greg asks.
Jack’s face lights up and he turns toward me. “Well, it’s a funny story, actually—”
“That we don’t need to get into right now,” I cut him off instantly.
“Oh come on, there’s nothing to be embarrassed about. It’s a great story.” When I make no move to share it, he turns back to Christine and Greg, his now-captive audience of two. “You could say she fell into my path.”
I slant him a look. “You could also say he blackmailed me into a date.”
“She was blowing a little hot and cold,” he tells them conspiratorially.
“The details aren’t important,” I say hastily, desperate to wrest back control of this conversation. “Long story short, we crossed paths at a cologne launch party for Eric Jessup a couple of weeks ago that I was covering for Siren. Jack happens to be friends with Eric, and he was kind enough to help me get a quote.” Downplay your professional competence so he doesn’t feel threatened: check!
Greg coughs. “Friends with Eric Jessup? Huh. That’s cool.” He eyes me over the rim of his glass as he takes a long swig of his drink. Pretty sure the poor guy’s head is about to explode.
“I apologize for my husband,” Christine tells Jack, patting Greg’s hand consolingly. “I didn’t give him enough notice about your identity, and he’s very starstruck. He’s trying so hard to be cool and just failing miserably.”
Jack chuckles. “I promise, most of the Brawler stuff is not nearly as exciting as it looks from the outside. Most days it’s just a job like any other.”
Greg considers that for about half a second. “I don’t believe you.”
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.