Chapter 3: Caffeine and Competition

A week later.

The weather had turned sticky, that late-spring humidity clinging to everything. I was running on three hours of sleep and a bad cold brew, when Zach still hadn’t shown up, but I ran into Sean first.

He wore a shirt washed so many times it was nearly white, faded jeans, and battered Converse sneakers.

He looked like a walking college cliché: broke but beautiful, with a laundry basket full of dreams. Even the laces on those old Chucks were fraying, like he’d been running from something his whole life.

Fresh-faced and handsome—the classic broke campus heartthrob.

He had that unpolished glow, the kind you can’t buy. Every girl from here to Lake Shore Drive would kill to have him save her a seat in Psych 101.

He got off the city bus, not even willing to splurge on an Uber.

His bus pass peeked out of his pocket, and I caught him glancing at the tap card reader as he stepped off—always keeping an eye on the fare. Sean, the guy who could charm you senseless but wouldn’t shell out three bucks for a Lyft.

Honestly, I have no idea where the three grand I give him every month goes.

Sometimes I half expected to see him on a milk carton: ‘Have you seen this boy? Last spotted disappearing student loans and sponsor money into a black hole.’

Don’t get the wrong idea.

People love to judge, but it’s not like I was running a charity. I got what I wanted out of the arrangement—at least, I thought I did.

He wasn’t here to see me; usually, I’m the one who goes to him.

Our roles were always flipped. I’d be the one calling, texting, driving to the wrong side of the tracks just to hand-deliver takeout from some overpriced sushi joint.

He’d picked up a part-time job at the coffee shop downstairs from my office.

Of course he had—Sean never could sit still, and the tips were probably better than he’d admit.

Looking like that, he naturally drew a crowd—girls lining up to ask for his number.

He had a following—little clusters of undergrads pretending to study just to watch him wipe down tables. The guy had no idea how magnetic he was, or maybe he did, but just liked to pretend.

Sean always turned them down, saying he already liked someone.

He’d blush, shake his head, mumble something about having his eye on somebody. It was almost sweet, if you didn’t know him.

Before, I would’ve confidently assumed that person was me.

Once upon a time, I thought my name was the one echoing in his head at night. I’d convinced myself that money and affection added up to love.

After all, I’m attractive, rich, and generous.

People say I’ve got it all together—good hair, killer suits, the kind of watch you only wear to board meetings. If there was a prize for Most Eligible Sugar Mama, my face would be on the billboard.

And let’s be real, the last part is what really matters.

Generosity pays the bills—and keeps the lights on in relationships like these. No one’s here for my sparkling personality.

If someone doesn’t like me, isn’t that just not liking money?

I’d tell myself that over and over, like some kind of charm to ward off disappointment. I’d laugh about it at brunch, pretending I didn’t care.

It’s not like I expect him to be madly in love with me. We’re all adults here. After taking so much from me, can’t he at least show a little affection? Otherwise, isn’t that just fake?

Sometimes, at two in the morning, I’d lie awake and wonder if I was just another line on his expense report. But I’d shrug it off—after all, we both knew the game.

I walked in and picked a seat at random.

The place was busy, all hissing espresso machines and indie pop on the speakers. Indie pop played too loud, and the chalkboard menu promised pumpkin spice everything, even though it was barely May. I slid into a window seat, pretending to scroll my phone, keeping Sean in the corner of my eye.

Sean didn’t notice me.

He was behind the counter, focused on wiping down mugs, his brow furrowed like he was prepping for finals. I knew that look: head down, heart somewhere else.

Just then, a girl walked in—dressed to the nines.

She breezed in like she was late for a Gossip Girl reboot, all silk and confidence. Heads turned. She had that glossy, old-money vibe, the kind you only get if your parents paid for your SAT tutor in fifth grade.

Sean saw her immediately and stiffened, nervous.

He went rigid—shoulders back, lips pressed together. For a second, I thought he might drop the mug in his hand.

She was wearing a Chanel-style suit, a MiuMiu hair clip—the whole rich-girl package.

Everything about her screamed North Shore—tailored, understated, but expensive enough to put some rent payments to shame.

Last time at the university, I hadn’t gotten a good look at her.

She’d been just another face in the crowd, all blurred edges and perfume.

This time, I saw her face clearly.

She had that Instagram-perfect symmetry, all high cheekbones and glossy hair. I watched her cross the room, like I was clocking a competitor.

I ran through the list of Chicago’s socialites in my head, but couldn’t place her.

For a second, I thought she might be a mayor’s daughter or the scion of some real estate empire. Nothing rang a bell, though. Maybe she was new in town.

While I was lost in thought, Sean’s face had turned bright red.

He was practically glowing, like a kid who’d just been caught sneaking out past curfew.

I heard him ask, a little tentative:

"Did you come here to see me?"

His voice was so quiet, I almost missed it over the hiss of the espresso machine.

The girl lifted her chin and said:

"No, I just heard the coffee here is good."

She didn’t even look at him. Her words were sharp, her gaze focused somewhere over his shoulder, like she was bored just being in the room.

If Sean had a tail, it would’ve drooped right then.

I almost laughed. You could see the hope drain out of his eyes, replaced by that same resigned stubbornness he always wore with me.

"Why don’t you recommend something?"

Her tone was brisk, like she was placing an order at the drive-thru. But Sean lit up, eager to be useful, to matter, even for a minute.

Sean immediately launched into a detailed explanation of every coffee on the menu, describing the origin and flavor of each bean.

He went into full-on barista mode, hands gesturing, voice brightening as he talked about the Guatemalan roast and fair trade beans. The kind of trivia that only comes from memorizing Wikipedia entries at three in the morning.

People waiting behind them got impatient and left.

I watched two grad students sigh and bail for the Starbucks across the street. Sean was oblivious, wrapped up in his pitch.

But the girl didn’t seem to listen at all; she just ordered the signature drink offhand.

She gave a dismissive wave and went back to scrolling her phone. If she’d heard a word he said, she didn’t show it.

Sean carefully explained how to drink it, warning her it might be a little bitter.

He slid the cup across the counter like it was a peace offering. I almost felt sorry for him.

In front of her, he was nothing like the person I knew—completely humble, almost fawning.

This wasn’t the Sean who’d ghost me for a week or roll his eyes at my gifts. Here, he was all nerves and wide eyes, desperate to please.

I wasn’t angry.

I expected to feel a spark of jealousy, but instead, it was just a dull ache. Maybe this was what letting go felt like.

Just confused.

It didn’t add up. I was the one who paid his rent, covered his bills, remembered his birthday. But none of that seemed to matter in this little scene.

Why isn’t he like this with me? I paid his rent, remembered his birthday, learned how he takes his coffee. What did she give him? Just a look.

A question I’d never admit out loud, but there it was, gnawing at me. What did she have that I didn’t?

I’m his sponsor, after all.

It felt like a contract he’d already forgotten, like all those dollars had just disappeared down the drain.

A moment later, it hit me, and I actually laughed out loud.

The barista at the next counter gave me a look, but I didn’t care. I realized—

He must think—

His youth, my three grand a month, the apartment I gave him, all those gifts—it’s an equal trade.

To him, it was just a business deal. No emotion required. A transaction stamped Paid In Full, with no interest accrued.

The men in my family have a long tradition of keeping people. I remember being twelve, watching my uncle slip a Tiffany bracelet onto a girl’s wrist and call it “just a thank you.”

It was practically a sport—my uncle, my cousin, my father. Different faces, same old story: pretty little things kept on retainer, paraded out for parties and whisked away when the fun was over.

I’ve seen them with college girls, actresses, even some professionals.

If you went to the right cocktail party, you’d see the same game played out over and over—just with better lighting and stronger drinks.

Not long ago, my uncle nearly got a girl pregnant and paid her half a million as a breakup fee.

Family legend, now. "It’s just money," they’d say, like it didn’t matter who got hurt as long as the check cleared.

A sponsor like me—generous and easy on the eyes—isn’t exactly common.

I knew my worth, but sometimes, late at night, I wondered if that made me better—or just lonelier.

Mutual consent doesn’t mean you’re not taking advantage.

There’s a difference between fair and right, but sometimes, it’s hard to see the line.

Before, when I spoiled Sean, I didn’t even care about the money.

I’d hand him a new coat, a pair of sneakers, a couple hundred in an envelope, and call it kindness. But I never asked what he really wanted.

He took it, but still stood me up again and again.

Maybe it was a test. Or maybe he was just scared to admit what we were.

Excuses: tutoring, part-time work, student council, lab assignments.

Every time my phone buzzed with a last-minute cancellation, I’d roll my eyes and act like I was too busy to care.

I never got angry. I even had the housekeeper make soup and send it to him.

If anything, I doubled down on the care packages, thinking if I just kept giving, he’d eventually give in.

Once, my dad caught me at it and thought I was dating. He warned me, "Don’t get too attached."

He’d looked over his paper, glasses sliding down his nose, and fixed me with the kind of look that says he’s been around long enough to know better.

My indulgence of Sean made everyone think I had feelings for him.

Even Ms. Williams gave me the side-eye when she saw the grocery bags. I guess, in their eyes, I’d crossed the line from sponsor to something messier.

Funny, really.

The whole thing felt like a bad sitcom, the kind where everyone but the main character knows what’s going on.

I used to think that, too.

Back before I realized you can buy a lot of things in this world, but not honesty—not from yourself, and not from anyone else.

Before I shipped my brother off to grad school in Boston and took over as GM, I’d never dated anyone.

My brother’s acceptance letter had felt like a free pass; no more excuses. Suddenly, I was the boss, and there was no one left to hide behind.

Not that I ever wanted to.

Romance was something other people did. I was content to run the show from behind the scenes.

I got bored watching, got up, and left the coffee shop.

The cup of coffee I’d ordered sat untouched. I pulled my jacket closer as I stepped into the muggy air, my heels clicking on the sidewalk in a steady, determined rhythm.

As I left, the bell over the door jingled.

I didn’t look back. But I caught Sean’s reflection in the glass, eyes following me out as if he had something to say and never would.

Someone behind the counter seemed to glance my way.

Maybe it was just the light, or maybe I imagined it—either way, I kept walking.