I was surprised that Love Hack thought this date was going well. Gretchen was even more striking in person, poised and unnervingly symmetrical. How could the smart glasses calculate with “68% confidence” that she was attracted to a guy with a lapsed gym membership and risk-averse career in finance?

 

“Ask a question,” Love Hack advised. It spoke through tiny speakers only I could hear. The volume was a tad high, but I didn’t want to fumble with the new gadget and risk revealing its purpose.

 

“How’s your linguine?” I asked, reading one of the conversation prompts glowing in front of me.

 

“Mmm. Very nice.” Dimples appeared on both cheeks when she smiled.

 

Suddenly, the sandalwood cologne I’d applied earlier at Love Hack’s suggestion smelled overpowering. I fought the urge to politely excuse myself from the table and drive home to my cat.

 

“You’re off to a great start!” Love Hack said, perhaps sensing panic. I felt like a total dirtbag using this thing, but I needed all the help I could get. I’d made it past a first date exactly once since reentering the market.

 

“So, Drew, I understand you grew up on the East Coast.” Gretchen speared a piece of roasted cauliflower with her fork. “Which part?”

 

“I’m from Philly.” I swirled my Barolo, mimicking Love Hack’s animation to look suave. “You ever been?”

 

“Uh-huh. I’m from back East too.”

 

“Based on her accent, there’s a ninety percent chance she’s from Massachusetts.” A scroll wheel appeared in the upper left corner, then resolved into a yearbook photo: Gretchen Walker, Waltham High School. Braces and a rugby jersey made her slightly less intimidating.

A red flag icon popped up. “It appears Gretchen lied about her age,” Love Hack reported. “Based on the graduation year, she is 37 or 38, but her dating profile states 32.”

 

Well, who didn’t fudge their profile? And this meant we were a similar vintage. I hated having to argue why younger people’s taste in music and movies were wrong.

 

“I have a confession,” Gretchen said. “I cyber-stalked you.”

 

“Really?” I asked, feeling a flicker of shame at her honesty. “Should I be worried?”

 

“I don’t know, should you be?” she asked.

 

“I… don’t think so,” I stammered.

 

“Relax, I didn’t find anything bad.” She smiled, revealing perfectly aligned teeth. “But I did see you worked at Titanium Capital. My cousin Michael’s there.”

 

“She’s referring to Michael N. Walker, Credit Analyst.” Love Hack displayed a LinkedIn profile, but it wasn’t necessary.

 

“Small world. How is Mike doing?” I asked, hoping I’d treated him as well as I remembered.

 

“He got married last summer.”

 

“I didn’t know that.” I’d lost touch with most of my old workmates over the last couple of years. Cancer had a way of clearing your calendar. “Please tell him congrats from me.”

 

“I will. He said you were one of the nicest people at the firm.”

 

“That was generous.” The running score estimating how attracted she was to me moved up a few points. But we were drifting towards a sensitive topic. My chest tightened. No sense hiding from it. “Did he mention my wife?”

 

Gretchen nodded slowly. “I’m sorry. It must have been so hard for you.”

 

“Her responses are slightly delayed.” Love Hack flashed a blow-up of Gretchen’s iris. “Pupil dilation suggests sympathy and emotional investment.” My attractiveness score jumped to 76%. “If you continue this line of discussion, you will greatly enhance Gretchen’s feelings for you.”

“There’s no reason to apologize,” I told her. Three years of bereavement support groups taught me to say it plainly. “I mean, I’d be lying if I said I was over anything and doubt I ever will be, but I am comfortable talking about it.”

 

“I hadn’t intended to bring this up,” she said, and I didn’t need smart glasses to interpret her expression.

 

“You didn’t — I did. I miss her every day, but I’m ready to meet someone new. She’d have wanted this for me.”

 

Gretchen nodded but didn’t meet my gaze, just pushed a noodle with her fork.

 

“Body language indicates emotional turmoil.” Several windows popped open in the corners of my vision. Posts scraped from Gretchen’s social media. A series of photos with her and a good-looking guy who appeared in nearly every selfie until three months ago. Love Hack parsed an obituary. “I’m 90% confident Gretchen’s boyfriend committed suicide.”

 

The hole this must have blown through her life.

 

“Are you okay?” I asked.

 

“Of course,” she said, now looking at me. “Why would you ask that?”

 

“You got quiet all of a sudden.”

 

“Did I?”

 

“If you provide emotional resonance Gretchen will find this attractive,” Love Hack advised.

 

“If there’s something you want to share, this is a safe place,” I said, reading the suggested dialogue verbatim. I wasn’t proud of this, but maybe Gretchen chose me because I’d been through something myself.

 

“It’s just… it’s not fair.” Her voice cracked. “Sorry. You don’t even know what I’m talking about.”

 

“Whatever it is, you’re not alone feeling that way.”

 

“Thanks.” She nodded. “Mike was right about you.”

 

“Emotional synchronicity achieved.” A road map scrolled across my vision — six conversational steps leading to intimacy with 98% certainty. A sure thing. And God knows I was lonely. But my stomach heaved. I wanted to crush the glasses under my shoe but instead just took them off and slipped them into my pocket.

 

“Let’s talk about something fun,” I suggested, relieved not to be taking direction from an algorithm.

 

“Okay,” she said. “Like what?”

 

“Movies,” I said. “I love classic rom-coms, but what about you?” I asked, not giving a damn how this might affect my attractiveness score. “What do you like? I really want to know.”