Page 5 of Falling For My Ex's Older Brother

Caleb considers this with an expression that suggests the question is mildly inconvenient.

"He's — I don't know. He's Logan. Driven. Very much about the business. We grew up different,you know? He took the company path and I went my own way, so we don't have a lot of common ground." He finishes this summary with the air of someone who has explained as much as they intend to.

"He's not exactly warm, from what I remember. But the company's legitimate, obviously. Top tier."

I nod and open my laptop again. Logan Drake, tech CEO. Not warm. Not close with his brother. That is the full picture, and it’s enough — more than enough — for a resume submission that may lead nowhere.

Caleb has moved to the couch, phone in hand, and has begun telling me about a scheduling conflict on his current project — something about a director's cut timeline and a producer he finds difficult. I listen with one part of my attention and rebuild my resume with the other, adding the skills and transferable experiences that will translate best to a tech environment. By the time he’s finished, I have a stronger document than I started with and a clear sense of what I still need to research.

He stays for dinner. We order in. He makes me laugh twice over something that happened on set, and the evening settles into the comfortable, low-grade warmth that has characterized most of our time together — not electric, not particularly deep, but familiar in a way I have confused with contentment for longer than I would like to examine. When he leaves just after ten, he kisses me at the door and tells me things will work out, and I believe him the way I believe weather forecasts — with measured confidence and no real certainty. I go back to my laptop and work until midnight.

***

The following morning, Caleb texts while I am formatting the final version of my resume — a quick message, efficiently delivered, confirming he has made the call.

Caleb: Spoke to the hiring manager. Her name is Patricia. She's expecting your resume today. No guarantees but she said she'd take a look.

Sutton: Thank you. I appreciate you doing that.

Caleb: Of course. Let me know how it goes. Heading into set.

I write a cover letter that takes me forty-five minutes to get right, then I send the resume to the contact information Caleb forwards, and then put the entire thing in a mental folder I labelpendingand close. I am not a person who waits well when waiting is the only available option, so I redirect the energy.

Drake Industries pulls up a clean, authoritative website — the kind that communicates competence without overselling. Founded by the Drake family, current CEO Logan Drake at the helm for the past twelve years following his father's transition into a board role. The company has divisions in infrastructure software, enterprise technology solutions, and an emerging AI development branch that is generating industry attention.The LinkedIn profile attached to Logan's name is spare — a headshot in which he is not smiling–but I see the salt and pepper hair, the chiseled jawline and the piercing blue eyes. There are some facial similarities to Caleb’s own, but from the photo, it seems more defined.

Below the photo there is a list of credentials that reads like a catalogue of strategic decisions made over two decades, no personal information whatsoever. There is nothing there that tells me who he is as a person, which may simply be who he is as a professional, or may be something else entirely.

I bookmark the company's career page. I research the tech sector the way I research everything — methodically, building from the broad architecture down to the specific details I will need to speak to the industry with credibility. I take notes. I identify the gaps in my current knowledge and locate the resources to fill them.

***

The official last day at the office comes four days later.

They give us the morning to collect our things — a courtesy that feels both generous and slightly clinical, the way a hospital discharge feels when you're not entirely sure you're ready. I arrive early, which is what I always do, and I stand at my desk for a moment before I start. It's strange, the way a space can look exactly the same and mean something entirely different. Same desk. Same monitor. Same view of the LosAngeles skyline doing its relentless impression of paradise. But the context has dissolved, and without it the furniture is just furniture.

I pack efficiently. I don't have much — I've never been someone who personalizes a workspace heavily, some instinct in me always keeping a slight distance between myself and any place I'm not certain is permanent. A small succulent on the corner of my desk that Jenna gave me when I started this job. My Cleveland mug, the one with the skyline on it that I brought from home and that got me teased exactly once before people stopped noticing it. A few books I'd wedged between my monitor and the wall. My notebook, which goes in my bag before anything else.

Marcus stops by while I'm packing the mug. He tells me I was always the sharpest person on the floor. He says it with the kind of sincerity that arrives two years too late to mean what it could have, and I thank him for it genuinely anyway, because it costs nothing to be gracious and I'm not interested in carrying anyone's failures out of this building with me.

Sandra hugs me at the elevator. She tells me I'll land somewhere better and I believe her, not because she's saying it but because I intend to make it true.

The elevator doors close. I look at my reflection in the brushed steel and I don't look like someone whose professional life just got restructured without her permission. I look like someone with a list and a plan and a notebook full of research she hasn't started yet.

The doors open to the lobby. I walk out into the October sun and don't look back.

By the end of the first week I have read more about general enterprise technology than I have about anything in the past two years, and I find, with some surprise, that I am genuinely interested. Not performing interest — actually engaged.

However, the silence thus from Drake Industries does not particularly unsettle me. I know how hiring pipelines work, andI'll take a lookfrom a hiring manager is a long distance from a formal conversation. I continue my research. I update my professional profiles. I respond to two other inquiries from firms in Los Angeles, attend one interview that confirms immediately that the role is not what I am looking for, and decline a second one before it gets that far. I know what I want. I have known for longer than I admitted, which is often how these things go.

My phone buzzes on the table and I grab it out of anticipation. However, it’s Jenna. Not a recruiter.

Jenna: Dinner tonight? My treat. I’m sure there’s a bottle of wine with our names on it somewhere.

I smile at my screen before I can help it. Jenna has a radar for when I need her that has never once failed to activate at the right moment — it's one of the things I love most about her, this particular gift for showing up at the exact right time without being asked.

I met Jenna the week I moved into my buildingthree years ago. She was in the hallway struggling with a piece of furniture that was approximately four times her size, and I helped her get it through her door, and she thanked me by producing a bottle of wine seemingly from nowhere and demanding that I stay and drink it.

We've been close ever since in the way that certain friendships form fast and hold firm — the kind built on shared sensibility rather than shared history. She's from Chicago, which made us Midwest allies immediately in a city that sometimes feels like it was built for people who never had to scrape ice off a windshield. We understand each other's references. We understand each other's particular brand of ambition — the kind that comes from growing up somewhere that taught you early that nothing is just handed over.