Cleo McDougal Regrets Nothing: A Novel

by Allison Winn Scotch

  I don’t know if you’ll even see this but if you do, I just wanted to say that I’m rooting for you, and it really makes me happy to see you succeed.

  All best,

  MA

  Cleo, unprepared for the ascent, was out of breath by the time Lucas had finished. Gaby, because she was training for the marathon, was not, and in fact had taken to running up the hill backward, then sprinting down it to meet them, then repeating it all over again. Also, she had barely slept last night after her evening with Oliver Patel but seemed not at all affected. That women in Washington (and beyond, of course) were judged on their stamina was utterly ridiculous, Cleo thought, as she watched her friend bounce up and back.

  “What happened with him?” Lucas asked as she jabbed the crosswalk light. No one in Seattle jaywalked, and Cleo was not about to break the rules of the city and be criticized for anything else.

  “It was high school,” Cleo said. “What happens with any of that?”

  Lucas narrowed his eyes, and because Cleo did not want him to disengage, she elaborated.

  “When your grandparents died, I guess my singular focus was moving on. Getting through that grief intact. Living up to their expectations of me, which, I mean, not to be a cliché, I could never now live up to. And part of that meant getting out of Seattle and just . . . getting through things. Forging ahead toward what I told them I would do: rule the world.”

  “It’s so nice here, though,” he said. “You couldn’t rule the world from here?” They each took a moment to look around, and each concurred that this was true. The air was squeaky-clean, the vibe was hip and electric, the mountains sprang up unexpectedly in the background with peaks dusted in snow. No one was in too much of a rush, but no one meandered either, and everyone seemed placid and accepting and, well, pleasant. You could just tell by the way people stood at the corner and waited for the orange hand to turn white and said “excuse me” when they stepped around you to peer at the coffee menu at Starbucks.

  Cleo exhaled, and the light changed, and they crossed the street while she considered how to best explain why she dumped an extremely sweet person who had only her best interests at heart.

  “It was nice growing up here, which is why I wanted you to see it. And I wish you could have met your grandparents, not just have seen the house that I grew up in. But . . . I don’t know. The longer I was here, the smaller it felt. I wanted to be the big fish in the big pond. That’s how I think I defined success back then.”

  “I think it’s how you define it now too,” Lucas said as he stopped and peered into the window of a tattoo parlor, his hand above his eyes, shielding them from the sun. Cleo yanked his arm.

  She didn’t press him because it’s a rough day for parents when they discover that their child’s wisdom has surpassed their own, even if that’s the entire point of parenting. So instead, she said, “You have to be eighteen to get a tattoo, and even then, it’s stupid.”

  “As stupid as running away when you were eighteen?”

  “Eighteen-year-olds make plenty of dumb choices,” Cleo said. “And I didn’t run away. I got into college. And then my grandmother died. And then what was I going to return to anyway? I wanted to go to law school. And then I wanted to get into Congress. And so on.”

  Lucas’s phone buzzed before he could reply. “Oh. That’s cool. He just wrote you back.”

  “He who?” Cleo asked. She was peering up and down the street, which looked nothing like the street she remembered from twenty years ago. There were espresso bars at every other storefront and impossibly hip clothiers and organic juice pop-ups and one store devoted entirely to essential oils. Georgie would love Seattle now, Cleo thought, and reminded herself to text her back. Which she already knew she would not.

  “Matty,” Lucas said.

  “Why would Matty be writing me back?”

  “Oh, I wrote back to him writing you in the first place.”

  Cleo stopped short, and a man with a handlebar mustache, a magenta vest, and rolled jeans, with an adorable yellow Labrador, nearly tripped over her.

  “Why would you do that?” she nearly screeched. The man did a double take, and so she offered, “Sorry, not you. Him, my son.” So the man flashed her a peace sign and went on his way, and Cleo thought this was a very distinctly Seattle interaction. And it slayed her just a little bit in the best of ways. Maybe you couldn’t run away from where you came from as easily as she had thought.

  “I didn’t, like, say that you loved him,” Lucas said. “I just said, ‘hey, thanks, nice to hear from you.’”

  “It wouldn’t be such a bad thing for you to have a little romance in your life,” Gaby butted in.

  “Where is this pizza place anyway?” Cleo barked. Nothing about this street looked familiar anymore. Back then, she and MaryAnne could have stomped down the avenue (in their Doc Martens, because in Seattle, even the semi-non-cool kids wore Docs) blindfolded and still found their way to Pagliacci’s. She spun around to the west, then the east, and was no better oriented.

  “I can ask Oliver about him,” Gaby said. They were striding down the next block, simply to move from point A to point B. “Maybe he knows his deal.”

  “Why would you ask Oliver about Matty? When would you ask Oliver about him?”

  “Oh, we’re having dinner tonight. I figure, we fly out in the morning; why not?”

  “Great,” Cleo said. “You both have dates tonight.”

  “Mine is not a date,” Gaby protested, but Lucas said nothing, which made Cleo wonder if Lucas really knew what a date date was, and if so, how he did and when he’d been on one. Also, should she bring up the fact that Gaby was reading his texts on the phone and maybe he was technically cheating on someone back home? She wanted to raise a man who respected women but she didn’t want to be a mom who snooped on her kid. Though she’d read some studies that she should be snooping on her kid, so . . . This whole thing was getting out of hand. All she wanted right now was a fucking piece of pizza.

  Before everything went south their senior year, she and MaryAnne used to split a Canadian bacon and pineapple pie. They’d trudge up the hill after school, on breaks from their homework and before going to MaryAnne’s (with the pool and the ping-pong table and the Pac-Man machine) and were at Pagliacci’s so often that the guys knew their order. They’d slurp their Diet Cokes until the ice rattled and pick the bacon off their slices and drop it on their tongues, nearly drinking in the grease. They’d talk about their own versions of ruling the world—it changed by the month. Sometimes it was through politics and sometimes it was through solving the hunger crisis in Africa or ending the Iraq War, and sometimes it was just making some boy who demeaned them feel small in a reciprocal way. Ruling the world could be both literal and metaphorical. This was before every T-shirt in the Gap screamed with quippy slogans like “This Girl Is on Fire” and “I Am My Own Future” and “#SquadGoals.” It was just them and their pizza and their aspirations.

  Today, in the bright and welcoming Seattle sun, Cleo landed on the block that she was certain was the block. But where she expected to find her old pizzeria, she instead found a vegan bar.

  “I don’t know.” She looked to Gaby and Lucas. “This was where it was.”

  “Maybe it closed.” Lucas looked unfazed, like her introducing him to Pagliacci’s wasn’t about to be one of her seminal parenting moments. “I don’t care; let’s just eat here. I’m fucking starving.” Cleo glared at him, which he ignored.

  “You know I’m avoiding gluten anyway,” Gaby added. Then she checked her phone. “Hmm. We’re back to about fifty-fifty on those YouTube likes.” She mulled something over. “Maybe we should rebrand the video with a snappy title, a headline like, ‘Cleo McDougal Has Regrets.’”

  “That’s not really snappy,” Cleo said. “That’s just a word-for-word interpretation.”

  “It’s a work in progress,” she replied, swinging open the door to the restaurant, which smelled strongly of wheatgrass and something so
unpleasant that Cleo almost gagged.

  All she’d wanted was a piece of pizza, a slice of her old life. She considered that all MaryAnne had wanted was a fair shot, a slice of her envisioned life.

  The hostess welcomed them and saw them to a table in the back.

  Cleo pored over the menu in search of something that could satisfy her craving. You got what you got. Sometimes you got an egg substitute omelet when you wanted Canadian bacon and pineapple pizza. Other times you were elected to the United States Senate while your former best friend ran for country club president. Cleo wasn’t one for tears, really wasn’t prone to complaining. Still, she could see where MaryAnne had a point.

  She’d much rather be eating a bacon and pineapple pie.

  SEVEN

  That night, Cleo was in the bath when the hotel phone rang. She never took baths back home—who really had the time for an indulgent bath as a single mother and senator?—but with Lucas around the corner at his coffee “hang” (his word, not hers) and her emails read and answered, she figured she would pamper herself. She was debating pouring in shampoo to make bubbles when the phone, conveniently placed by the hotel on the wall next to the toilet, buzzed. She sighed, her serenity disrupted, and reached for it, her arm damp and spilling water on the floor. For a moment, she envisioned herself as a heroine in a romantic comedy, taking calls while in a (shampoo) bubble bath and living a delightfully quirky life.

  “Hello?”

  “Senator McDougal, there’s a Matty Adderly here for you.”

  “A what?” Cleo sat up abruptly, and more water sloshed over the lip of the bath. “I’m sorry, a who?” (Grammar was important to Cleo, naturally.)

  “A Mr. . . .” The concierge paused, said something with her hand over the receiver. “Yes, a Mr. Adderly is here.”

  “I don’t . . . What?” Cleo squeezed her eyes shut. Had Facebook developed a technology where you stalked someone on his page and then he was shown your location and just magically appeared? Or maybe Matty was the one who was stalking her? Had she been photographed entering the hotel, and he just decided to come over? Cleo knew her recognition was on the rise (thanks, MaryAnne Newman!), but this seemed a little outlandish.

  “Should I tell him . . . ?” The concierge seemed as confused as Cleo, though not for the same reasons. Obviously. It wasn’t her high school boyfriend who had appeared in the lobby out of nowhere after two decades of distance.

  “I guess; I don’t . . . Can you please ask him to give me about fifteen minutes? I’ll meet him in the bar.”

  She heard the concierge convey the message.

  “Very good, ma’am. He’ll see you there.”

  Cleo stared at the ceiling, recalibrating, then stood, grabbed a towel, and pulled the plug on the drain. Goodbye, shampoo bubble bath, she thought. It would have been nice. As she shoved her arms into a violet-hued blouse (she often wore violet, as the color brought out the blue undertones in her eyes and was always her mother’s favorite) and tugged on a pair of jeans, she resolved to chew out Gaby on the plane for setting off this entire godforsaken misadventure. Cleo was not interested in revisiting her past, relitigating her mistakes, falling in love with boys she hadn’t really been in love with in the first place. Cleo was not the heroine in a romantic comedy. And frankly, given that, at last glance, the comments and likes on YouTube and Twitter were trending toward MaryAnne, Gaby should know this and shut this whole thing down.

  She swiped on blush and lipstick and brushed mascara over her lashes (because she was not a monster) and let out the topknot on her still-in-need-of-highlights hair. She wondered if she looked too much like she was indeed prepared to fall in love with Matty and considered changing. The blouse was a little too romantic, flowy and ethereal, but when she opened her suitcase, she found she hadn’t packed appropriately, so it was this, her workout clothes, or an athleisure hoodie that she wanted to save for the plane.

  As she rode the elevator down to the lobby, she tried to think if she’d ever added Matty to her list of regrets. She wished that she’d reread the 233 items more carefully. He was probably on there somewhere. Nothing sweeping like: Shouldn’t have dumped Matty because he was the love of my life but something smaller like: Should have appreciated his generosity. Though, she pondered as the elevator door dinged open, that’s not such a small thing after all.

  She saw him before he saw her, which was the benefit of arriving second. Sometimes, when she was entering a tough negotiation with her colleagues in one of her Senate committees, she (and they) employed this tactic. Arrive last. It made you appear less eager, less ready to compromise. Of course, sometimes you wanted to arrive first, just to let them know that you were a baller. (Being a senator was sometimes confusing. You’d never hear anyone admit to it, but it was true.)

  She held her breath, blew it out, then strode through the restaurant to the bar, which was surprisingly crowded on a Sunday night at eight p.m., but Seattle was cool, so maybe no one worked on Monday. She didn’t know.

  Cleo tapped him on the shoulder, and he spun around on his stool, startled, like he wasn’t sitting there waiting for her, nursing his beer. Even in the dimmed light, Cleo could see that he looked exactly like he used to, only a little craggier, which served him well. His blond hair was still thick; his stubble hadn’t grayed. He stood to hug her, and he hadn’t shrunk. (Why he would, Cleo didn’t know, but still, she thought it.)

  “Clee!” he said with nothing but delight. “I’m so happy to see you. Thanks for reaching out.”

  She pulled back from his hug, because Cleo was always the one leaving hugs first, and plunked onto the stool next to him.

  “I didn’t know what to order you,” Matty said, an apology. “I couldn’t remember what you would drink.” So still just as nice as ever.

  “I didn’t really drink in high school, so you wouldn’t have known.”

  “Well, then, that explains it!”

  The bartender swooped over, and Cleo ordered a martini.

  “I’m glad I didn’t get you something,” Matty said. “I would have guessed wine.”

  “In Washington, you need a stiff drink more often than you realize.”

  Matty laughed at this, and Cleo relaxed just a little bit. She didn’t even know quite why she was so on edge. Maybe too many ghosts from the past in one weekend. Gaby had thrown her on a plane, and the next thing she knew, she was standing in front of MaryAnne Newman (and the rest of them), and then she was standing in front of her childhood home, and now she was (figuratively) standing in front of a boy whose heart she had broken (rather callously), and she hadn’t really asked for any of this. Cleo swallowed. She did not like to think of herself as a victim, even if it were just a victim of Gaby’s plans. She thought of herself as a woman in charge, in control, both hands on the steering wheel.

  So of course she went and ruined whatever ease had just passed between them. “Look, I don’t mean to be a jerk, but I’m confused about you being here.”

  He looked confused at her confusion. “Um, you sent me a note on Facebook?”

  To which Cleo was even more confused. “I . . . I mean, I don’t really use Facebook. My son set up my account.” She stopped then and realized exactly what had happened. Lucas, her morose, grouchy teenager, was actually the sidekick in her romantic comedy. “Oh. Oh, OK, no, I see. He must have . . .” She waved her hand and wished very much that she had a martini in it.

  Matty took out his phone and offered it to her, the message on display. Indeed, she had invited him for drinks at about eight p.m. So he was less of a stalker than she’d thought.

  “My kid,” she explained. “He’s out on his own date . . . with MaryAnne’s daughter. And I think he probably felt sorry for me.”

  “I don’t mind,” he said. “I’m just happy to see you.” (So, so nice.) “Though that must be weird.”

  “Having a kid?”

  “Out with MaryAnne’s daughter,” he clarified, and Cleo winced. She was so goddamn off her game.


  “Oh yes, well, trying to adhere to the adage that if you tell a teenager not to do something, they’ll just want to do it more. If I say he can’t speak with her, they’d probably run off and elope. If they could.”

  Matty contemplated this, sipped his drink. “I don’t think I was ever the type of teenager who had to be told not to do something.”

  “Yes, you were always very sweet.” He was the one who winced now, and then the bartender brought Cleo her blessed martini. “I meant it as a compliment,” Cleo said, after drinking an oversize swallow quite gratefully.

  Matty shared his story quickly, in less time than it took her to drain her glass. He’d been married just out of college but only for two years. “A starter marriage,” he said with a casual shrug that belied what Cleo could see was still a bruise that smarted. “In fact, she also said I was too nice.” Since then, it had mostly been about his work as he rose through the ranks at Microsoft, and he now had an expansive loft just around the corner from the hotel, with a view of the Puget Sound and flat-screens in too many rooms.

  Cleo didn’t know why it surprised her to hear that he was so successful—probably because she thought of herself as someone who read people well. You had to be to juggle so many different personalities within your constituency. Matty hadn’t been anything special in high school, no gem to be fashioned out of coal, no brilliant mind, no honor roll. But maybe he had layers she hadn’t seen, or she had been so wrapped up in her tunnel vision, in her specific definition of success, that she’d missed it. Cleo her whole life had been taught by her parents that intelligence and drive were really what you needed to get by. Her dad had been an engineering major, then a helicopter pilot in the army reserves before moving to Boeing. Grit, grit, grit. Even in her artsy mother: you don’t become a member of the Pacific Northwest Ballet at eighteen on luck. Hard work, effort, grit, that’s what got her mom there. Cleo glanced at Matty now, content and gracious and certainly accomplished, and wondered what else she placed a high price on that was less valuable than she thought. Whoever said you had to be the smartest person in the room? (Well, in fact, Cleo had said that. But figuratively speaking.)