Chapter 5
JOHN
ONE WEEK AGO
I’ve been so focused on wooing a sixty-two-year-old British professor lately that when Monty asks me what’s up in my personal life, I have to think long and hard to remember the last time I took someone out on a date.
It was two months ago. The daughter of one of my MIT profs was in Palo Alto for job interviews, and I had agreed to take her to dinner.
She was attractive and friendly, and I was so bored that I faked a migraine at the end of the night.
There are a few women who regularly text me to see if I want to “hang out,” and occasionally I do “hang out” with them as a means of relieving stress.
And then I leave as soon as they start asking me if I ever get lonely.
I never get lonely. Ever. But I do miss certain people, including Monty. He has established himself in Chicago as the tech guy at a major venture-capital firm. I keep asking him to come out to Palo Alto to work with me, but he refuses. It’s a shame.
I choose to tell Monty that there’s no one special at the moment and that a high-end matchmaking service routinely reaches out to me to see if I’m interested, but I’m not.
“Why aren’t you interested?” he asks.
The restaurant he’s chosen is crowded and noisy.
It’s unlike him to choose a place like this.
Halfway between his hotel and my apartment, I suppose.
I pretend I didn’t hear him as I finish my glass of Malbec.
He won’t let me get away with it, but it gives me a moment to practice my I’m definitely not thinking about your sister right now face.
He leans in across the table and speaks louder. “Why aren’t you interested in the matchmaking service?”
We don’t talk about our personal lives very often. There is so much else for us to talk about. But ever since Monty started dating a woman in Chicago who he really likes a few months ago, he has gotten more inquisitive.
“Busy,” I say.
“That’s exactly why people use the service.”
“Is it?”
“You aren’t hung up on that model, are you?”
“God, no.”
“She still stalking you?” he asks.
“I wouldn’t call it stalking. She only showed up at my house that one time. And the new doorman in Tribeca isn’t a pushover like the old one. Last I heard, she’s in Europe. I haven’t responded to her texts or calls for months, so she hasn’t done it much lately.”
“Are you hung up on someone else, then?”
He studies my face, and I give him as blank an expression as possible. “Like who?”
He watches me for another beat before shrugging. “I don’t know. Women still ask me to introduce them to you, you know. Katie’s friends. Especially since that TED Talk.”
“I didn’t know people still watched those.”
“It went viral,” Monty says. “Do you not know that? On YouTube. Clips on Instagram. Apparently, you looked ‘dreamy’ and seemed ‘really nice and articulate for a nerd.’ I don’t tell them that it’s because you’re giving a talk and not talking to or with anyone.”
“You don’t think I’m nice?”
“’Course I do. It’s just never been a priority for you to convey it.” He gets all googly-eyed for a second. “Katie’s nice. She’s really nice.”
“So you’ve mentioned.”
He appears to be waiting for me to say something else, but I don’t.
“It is customary to say that you look forward to meeting my girlfriend,” he says.
“I do look forward to it. But the last time I met one of your girlfriends, you told me you were done introducing me to your girlfriends.”
“You told her she was puerile.”
“And she had no idea what it meant. Which, as I recall, was one of the reasons you gave for breaking up with her,” I say. “I thought your coworker was an asshat too. What was his name? Daryl?”
“Correct. I did decide that I’d never introduce you to anyone I care about even the slightest bit ever again.”
“Which is why I don’t bring it up. Although, to be clear, I would like to meet the woman who makes you this happy.”
“I am happy.” Monty smiles dreamily. “You should give my sister a call,” he says without signaling a change of subject first.
I get risotto caught in my throat and start coughing. “Really?”
He’s studying my reaction. I wipe my mouth with a napkin. I think my teeth are chattering. My palms might be sweating. This is not optimal.
“Yeah, I mean, I know you’re busy. But I worry about her out there on her own.”
“I thought she had a roommate.”
“She does, but I mean, she…you know, she’s so free-spirited. Olivia, I mean. And I just…”
Something about his expression makes me sick to my stomach all of a sudden. “Did something happen?”
“No, no. Not really. My mom just mentioned that she was doing some modeling gig with a photographer, you know, and he was…unprofessional. She got out of there before anything happened, but I guess it spooked her.”
My hands are balled up into fists on my lap. My ears feel hot. I have no idea who this photographer is, but if he were in front of me right now, he would be the first person I’ve ever kicked the shit out of, and I would feel so good about it.
“I’m sorry to hear that,” I say carefully. “What can I do?”
Monty polishes off his bourbon and looks at me for a long time before saying, “Just let her know that you’re there for her, I guess. As a friend of the family, you know. So it doesn’t feel like such a big city.”
“Of course. I’m sorry I haven’t done that yet—I didn’t think you’d…”
“I never told you to stay away from her.”
“Right, no, I guess…” I feel my cheeks getting warm. I force a little laugh. A chuckle? I’m chuckling.
“Are you still choking on that risotto?” he asks.
“No. You’re just such an overprotective dick about your sister with most guys, I figured I should keep my distance.”
“Why would that be?” He leans forward again, hunching over as he squints at me. He has watched too many mafia movies. It would have been cooler if he’d leaned back casually, like Han at the cantina with Greedo. “You feel guilty or something?”
“’Course not. I have nothing to feel guilty about. Just saying you’ve always been an overprotective dick about her, and I’d rather not deal with it.”
Monty seems satisfied with that explanation, so I feel comfortable breathing again. He hails the waitress and asks for more wine and bourbon. He moves on from the subject of his sister to his own business. I can have this conversation in my sleep, so I let my mind drift to Olivia.
She has been living within driving distance of my house for over a year now.
Not that I would have had much time to visit her, but now that I’ve got the green light from Monty, I need to make the most of this opportunity.
I need to think carefully and strategically about how to approach this.
Or…I will wait for an opportunity to present itself.
Let the algorithms of the universe show me what I need, when I need it.
I’ve laid the groundwork. I’ve certainly achieved everything I set out to achieve in order to win her over. I just need a plan.
I can’t honestly say that I’ve consciously thought about Olivia every day over the past couple of years since I saw her dance in Pittsburgh.
But she’s like an all-time favorite song that passes through my consciousness on a regular basis, even when I don’t purposefully stop to listen.
I smile and savor the thought of her. Whenever I hear a piece of music that stirs me, I wonder how it would affect her, how her body would move to it.
Of course, she makes regular appearances in my fantasies—that goes without saying.
But I’ve felt good, just knowing that she’s out there and that one day we’ll be together again.
I suppose I just didn’t expect one day to come so soon.
I’m right in the middle of launching a foundation, and I’m at a critical juncture with my food-tech play. The timing isn’t ideal. But I’ll make it ideal.
Suddenly I feel nervous about seeing her in person.
This young woman who was just a baby when we first met.
Who probably still thinks of me as a dork.
But I will apply my no-fail entrepreneurial spirit to winning her over.
Every success story in Silicon Valley begins with a nerd who never believed for a second that the thing he’s envisioned wasn’t possible.
I know the fact that we’ve known each other since childhood is both a blessing and a curse.
She thinks she knows me, and that’s good.
I understand things about her that other men don’t, and that’s good too.
But one of the things I understand is that she will always think of me as Johnny B. Nerdballs, and that…is not great.
It’s a hurdle, not a brick wall.
I’m ready to make a run at it and take the leap.