An Impressive Proposal

Chapter One

Jackson

I fidget with a loose thread on my brand-new, ill-fitting suit as I stand outside the auditorium where my best friend is currently walking across the stage. The cellophane wrap crinkles in my hand as I loosen my vice grip on the bouquet of pink and white peonies, her favorites.

I should have asked Penny Thompson out years ago, but I was too much of an asshole at the time, and let’s be real, it’s not like I could afford to give her anything she deserved. It isn’t hard to see that she’s used to the finer things in life, like her G-Wagon and her designer bags.

“Is that your girl?” my brother and business partner, Marcus, asks, pointing at the tiny figure walking across the screen. I wasn’t lucky enough to get tickets to the actual graduation ceremony, so like all the others who couldn’t get in, I’m standing in the reception hall watching the live feed.

Penny gives the dean of the College of Arts a shy smile as he congratulates her and passes her diploma over, and my heart trips over itself in my chest. I dropped out of Wellerton College my junior year to start a tech company with my brothers, and now that there seems to be a bit of steam, I might actually have a chance to show Penny that I’m not worthless.

Not that she would ever think that of me. She’s never acted like I’m lesser than, like I’m unworthy of her presence. Honestly, she’s nothing like I expected a rich heiress to be. She’s quiet and reserved, and we met during her freshman year when I was running new student orientation, and it turned out I was also her dorm’s RA. We barely even spoke until I heard a knock at my door late one night while I was studying for a business final.

“My room key isn’t working,” she said, panic and tears welling in her eyes. “And my roommate isn’t here.”

I hadn’t been able to solve her situation until the next morning, but I’d allowed her to sleep in my room while I slept on a sofa in the student lounge that night, and we’ve been close ever since. I learned that she was a business major like myself, but she’d been considering switching to art.

When we returned from winter break for the spring semester, I’d been overjoyed to find out that she did, in fact, make the switch, and I would often study for my business administration courses while she sketched or painted.

“That’s her,” I breathe, nervous energy fluttering through my veins. When she comes out, I’m going to ask her out to dinner. I’ve made reservations at a decent restaurant that has a dress code and everything, and I’m actually going to pay for once. Usually, before I can even try to offer, she’s the one to order us delivery or take us to dinner, although we’ve never gone somewhere nice.

“She looks good today,” Marcus observes, and anger and jealousy flicker through me.

“Don’t even think about it,” I growl.

Marcus has always been the smart one, the one whose praises are sung everywhere he goes. He graduated high school at sixteen, and he dropped out of Wellerton two weeks into his freshman year to start Kane Security, and it finally seems to be going somewhere half a decade later.

Meanwhile, I’m lucky to even have a seat at the table in this business. Sure, my grades were decent, but it was my interest in people that got me where I am. If I can study someone, I can determine how I’m supposed to act, down to my mannerisms, to get them hooked.

Penny is the only one I’ve opened up to, but even then, she doesn’t expect me to talk. We’ve spent many a hangout in utter silence, and now that I have my own apartment, she often comes over and starts painting without a word while I work on the business, trying to reel in more new clients. It’s been a lot busier since I finally graduated last year and moved to working eighty hours a week.

Marcus holds his hands up in surrender. “Dude, I’m not after your girl. Just commenting.”

I prick a brow at him. He’s a year younger than me, but he’s always been the family genius, the one with all the ideas. He’s the reason we started the business in the first place, because he saw a glaring hole in the cybersecurity market and decided to fill it, giving his brothers the first shot to get in on the ground floor. Some people thought it was insane to trust a sixteen-year-old working in security, and they thought it was worse that he was hiring his siblings to work with him.

“Good,” I say simply. Marcus has met Penny a few times by now, and I’ve never been quite so tense about the two of them being near each other as I am today.

When the ceremony is over, I stride over to the door and straighten my tie, swallowing down any remaining nerves.

I’ve spent weeks planning this date with Penny. If it is a date, anyway. If not, fine, but I will be taking her out to celebrate no matter what. While she’s been stressing about her fine art finals, I’ve been making calls and pulling strings.

And this morning, I picked up my brand-new used car, the first one I’ve ever had just for myself. It’s a plain tan sedan, but it has air conditioning, a functioning radio, and less than a hundred thousand miles on it.

The doors open, and I brace myself against the flood of people exiting the auditorium.

“Jackson!” a familiar voice shouts, and my heart warms as I reach a hand out and pull her against me.

I wrap my arms around her, breathing in her comforting and familiar vanilla scent. “I’m so proud of you,” I whisper just for her.

A throat clears behind me, and I release Penny reluctantly. “These are for you,” I say, holding out the bouquet.

She grins, and her eyes sparkle as she brings the flowers closer to her.

“They’re beautiful,” she says, speaking up to be heard over the growing cacophony of people. She glances to the side, and her smile gets wider in a way that sends a dagger of ice and jealousy through my heart. This bright grin is one I’ve never gotten for myself. I’ve only ever seen her use it on other people. “Marcus, you came too!” She gives him a little half-hug, and I have to look away to keep from doing something incredibly stupid.

“Mrs. Thompson,” I say after spotting her mother exiting the auditorium just in time.

The older woman gives me the same warm smile that I’m used to seeing from Penny. “Jackson, how many times have I asked you to call me Lucy?” She opens her arms for a hug, and I step into them willingly. Ever since Penny introduced me to her at the end of her freshman year, Lucy Thompson has treated me like family. Considering my mom has barely been around and I practically had to raise my siblings, it’s an amazing feeling.

She pulls away and evaluates me, and it feels like more than her usual looks. While Penny is distracted by my brother’s chatter about a coding problem he can’t seem to solve, Lucy tells me, “Alright, kid, let’s go for a stroll.” She glances up at her daughter. “Pen, I’m going to stretch my legs. Meet me at the bench in twenty minutes and we’ll get lunch before I have to head to the airport.”

Penny smiles and waves her off.

Like every event I’ve ever attended in the last four years, her father is notably absent. Probably too busy enjoying the perks of his wife’s money to show up for his daughter’s graduation. One night years ago, Penny cried in my arms about why her dad didn’t love her, and I couldn’t do anything but rub her back and hold her.

My body tenses as Lucy takes me out into the sunny afternoon. “So, what are your intentions with my little girl?” Her voice is humored, but there’s an edge of seriousness to it.

I go with the simplest option. “Since you have to fly back to London tonight, I thought I’d take her to dinner to celebrate.” I leave out the core of the matter. That I’m going to tell Penny how I feel, and that I’ve been praying she might reciprocate those feelings.

Lucy nods. “Are you going to tell her that you’re in love with her?”

My face heats, and my shoulders tense higher. Of course she’s noticed. It seems like the only one who hasn’t noticed me is Penny. “I…might.” No sense in hiding it now. Have I really been that obvious?

She smiles up at me gently. “You have nothing to worry about. That girl is obsessed with you. I’m just surprised it’s taken you this long.”

I relax marginally. “You’re not mad?” After all, most people would look at me and call me a gold digger, going for someone so far out of my league that we aren’t even playing the same sport.

She laughs. “You’re a good kid, Jackson. All I ask is for you to be careful with Penny’s heart. She doesn’t use the caution that she maybe should, and that’s probably my fault. She’s always been sensitive, which isn’t a bad quality, but it also means she’s fragile.”

I nod. I already know this about Penny. We’ve been best friends for four years, so I would have had to be blind to not notice the way she flinches at the anger of others, even when it isn’t directed at her. She isn’t built for the type of pain the world offers.

“I feel like I’m finally starting to be worthy of her,” I admit, gesturing toward my new suit. “I have my own place, and I just got my own car. I don’t know everything about your world, but I do know that she deserves better than me. If I do get an opportunity to be with her, I won’t waste it.”

Lucy tilts her brows and gives me a painful smile I understand all too well. She pities me. “Oh, Jackson, Penny would never care about all that.”

I shrug. Maybe she’s right, but I do care about it. I don’t want to be that useless guy who can’t pay his own way, who expects his woman to pay for everything while he takes advantage of her kindness. “I know,” I say.

She adjusts my tie for me, and I frown. I hadn’t even noticed it going a bit out of place, the shoddy knot loosening during the short walk.

“Thanks,” I say, my face hot with embarrassment.

She puts her hands on my cheeks in a motherly gesture. “I’ll talk to her over lunch and see what I can find out.”

“Alright,” I say. That’s more than I could have possibly hoped for, although she might just reveal that Penny has no interest in me, and then Penny will feel awkward and decide not to go to dinner with me at all because, as it turns out, I’m really not good enough for her.

* * *

PENNY

When I stroll up through the quiet garden path where Mom and I always hang out on her visits, Mom’s hands are on Jackson’s face. I recognize her expression as her “serious talk” face, and my heart trills as I wonder what they’re talking about.

I back up a couple steps so I’m behind a bush, straining my ears.

“I’ll talk to her at lunch and see what I can find out,” Mom says, her tone gentle and pleased. What is she going to find out?

I hold the flowers closer to my chest. Have I been acting weird? Is Jackson annoyed by my presence? Is Mom going to ask why I can’t take a hint?

I breathe in the sweet scent of peonies, reasoning with myself the way my therapist has taught me. If he’s sick of me being around, why did he bring me flowers? Why did he come to graduation at all? I didn’t invite him, because I figured he was busy with work. Sure, I told him the date, but it wasn’t a blatant invitation.

Maybe I was too enthusiastic about talking to Marcus. Does he think I have feelings for his brother? Is that what it’s about? Or maybe Marcus has feelings for me. He did talk to me for a solid ten minutes straight when Jackson and Mom left. Well. He talked at me.

Oh, god, I hope Marcus doesn’t want to ask me out.

It would be hard to reject him kindly when the truth is that I’m in love with his brother. Even though Marcus and I are closer in age, I’ve longed for Jackson since the moment I met him at orientation. Some of my girl friends would say it’s because of his bad-boy persona, or that sexy smirk.

It wasn’t any of that, though. It was a moment he doesn’t even remember, or if he does, he doesn’t know it was me. I’d shown up to campus excited about orientation, but I was told by a confused and apologetic RA that they didn’t have a room for me. They’d mistakenly missed me in the system, and I was able to pretend everything was fine for a while, lying to Mom that I wanted to do the day myself, that I could get things up to my room. My nonexistent room, which she still has never found out about.

While everyone else was excitedly setting up their dorms and meeting their roommates, I was crying behind this very bush when his warm voice asked, “Are you alright?”

It wasn’t overly alarmed, but a smooth silk that soothed me with every word. Instead of waving him off like I had my mom, I said, “They don’t have a room for me. I don’t know where I’m gonna live!”

He hadn’t been looking my direction through the leaves of the bush, but I peaked to see the handsome frown on his face. “I’m an RA. Someone on my floor dropped out this morning. What’s your name?”

I wrapped my arms around myself. “Annette P. Thompson.” I’ve been going by my middle name ever since I watched the movie Penelope as a kid, although I’ve since shortened it to Penny.

By the time I made it back to the registration desk, the young woman who’d denied me grinned and waved me over. “It turns out we do have a room for you, Annette!”

I smiled at her through the lump in my throat. “Penny, please. I prefer my middle name.”

Jackson’s voice drags me back into the present. “Alright.”

Alright? That’s it?

He doesn’t elaborate, doesn’t repeat what he said before. Frustration wells within me. This is the same spot where we first met, and it was supposed to be the spot where I was going to confess my feelings for him now that I’m no longer burdened by the pressing weight of majoring in art whilst minoring in business administration. I promised myself I wouldn’t do anything to distract from hitting my degree in four years, but now that I’m free of it, I want more.

For example, I want to find out if Jackson would actually do the things I’ve dreamt of him doing to me, only to wake up unsatisfied and frustrated.

It doesn’t seem like they have anything else to say, so I walk around the bush and slap a grin on my face. “You guys talking about me?” I ask with a chiding, humorous tone to my voice.

Instead of denying it, Jackson’s face flushes a deeper shade of red than it already is.

Mom gives me a smile. “Baby, I am so proud of everything you’ve accomplished. How about we go to Joe’s as a mom-daughter date before you hang out with your friends for the evening.” She looks at Jackson meaningfully when mentioning friends, and I pretend not to catch the gaze.

“Sounds great! Let me just talk to Jackson real quick and I’ll meet you at the car.” I’d greeted her the moment she arrived, so I know exactly where she’s parked. She’s one of the university’s top donors, so it isn’t hard to find her personal parking space by the engineering building where she studied for her doctorate.

I give her a hug and kiss on the cheek, and when she walks away, I turn all of my attention to Jackson, who’s…looking anywhere but at me.

“Did you enjoy your talk with Marcus?” he asks, and my heart sinks. I knew it. He’s never brought any of his brothers to any of my events before, and I’ve only met Marcus at their shoddy downtown office a few times.

I shrug. “I didn’t know someone could talk so much about computer coding.” It’s not Marcus’s fault he is the way he is, but I much prefer the quiet serenity of hanging out with Jackson.

He nods. “Right. Yeah, we’ve been having some trouble at work.”

There’s an awkward pause, and I start to speak.

“Did you want to—”

At the same time, Jackson says, “I was thinking we could—”

We stop speaking simultaneously. It’s never been this awkward between us. Whatever Mom wants to ask me about, it’s serious, and just like that, my therapy goes out the window.

“Are we okay?” I ask, hugging the flowers against myself so tightly that the stems bend.

He swivels his head toward me. “Of course, why wouldn’t we be?” His eyes have that concern and sadness that I always wish I could erase away.

I take a step closer. “You’re just being a bit different, that’s all.”

He gives me a pained smile. “I just have a lot on my mind. Maybe we could…talk about it over dinner?”

Over dinner?

“Like…as friends?” I ask carefully, not wanting to assume. Jackson has never asked me to go to dinner with him. Usually, if we do eat together, it’s because I buy something and practically force him to eat it. He’s tall and lean, and not in a way that seams healthy, but like a guy who’s skipped way too many meals. Lately, though, he’s begun to fill out. Not much, but enough for me to notice.

He contemplates my simple question for what feels like an eternity. “If that’s what you want.”

What the actual hell is that supposed to mean? Is he asking if I want to get dinner? Or, my heart begs, is he asking me on a date?

“I would like to have dinner with you,” I say, careful to guard my heart. This is probably nothing. Nothing at all.

He smiles, but that pain is still etched in his brows. “Do you want to meet me at Joe’s at six?”

Joe’s is a pricier place. I usually stick with less expensive places when picking meals, mostly because, while most students don’t get an allowance from their parents during college, my allowance for food, drinks, clothes, and even extra art supplies is only a grand a month, and I spend most of it on art supplies. Still, I know I’m more privileged than most of my friends at this school, so I like to be the one to provide meals. I would rather gnaw off my own arm than tell Jackson that I survive off ramen noodle packets when he’s not around.

“Six is great,” I say, my heart racing in my chest. I can’t handle the not knowing, but it would be so much to ask and get rejected right now. I think I would shatter into a million tiny pieces if he rejected me, and I do still have to have lunch with Mom.

By not asking, I can have a few more hours of knowing that he’s still my best friend.