New Winslow S6E6

Cleo hadn’t expected her first time back in Boston in months to be so anticlimactic. She wasn’t doing anything beyond working while she was here. She wasn’t going to sit in any of these restaurants with her friends and enjoy a meal in the warm glow of the fireplaces and intricate light fixtures. No, she was coming in, waiting around, getting food, then diving back into Boston traffic in order to deliver it to expectant customers.

She was in Allston-Brighton, a neighborhood fairly far away from her old one, but still as familiar as an old sweater. She’d gone to school at Berklee College of Music, over in Back Bay. It had been walking distance to some of the Allston clubs the older students introduced her to when she was young. Later, she’d started her career playing at these same clubs. Some still existed while others had folded as the city got more expensive. She felt a pang as she passed by the club where she’d played her first non-school gig. It was a bank branch now, just a little place with an ATM and a sterile front office.

The night she’d played there, Andrew had made a point to come see her first show. He’d been so anxious about being in a crowded club that he’d gotten too drunk and thrown up in that alleyway after her set. But his support had buoyed her, and she’d gotten a great review from a local blog that had long since stopped updating.

The place she was picking up from had been a little Mexican grill back then. Now it was a smoothie store that was also likely a multi-level marketing front of some sort. The smoothies were outrageously expensive and so full of sugar that there was no way they were benefitting anyone. Cleo perused the chalkboard menu as the college kid behind the counter got her order packed up and ready for her. They all looked delicious, but this wasn’t healthy food and the customers were clearly paying a premium based on the idea that it was.

God, she could almost hear Liv’s voice beside her as she looked at the offerings and their prices. Before she could talk herself out of it, Cleo snapped a picture of the menu and texted it to Liv.

“All set.”

The kid’s voice broke through her thoughts. Cleo got the bag and said a quick thanks to the kid, who nodded and turned back into his work. She stepped aside so that a young couple could walk up to the register, marked the order as picked up in her phone, then hurried outside.

Her car was parked halfway down the street in the only empty parking spot Cleo could find. A sharp wind blew her long black hair into her face as she walked with her head bowed, bag clenched in her hand. Her hands were numb in the cold air. Wasn’t it supposed to be getting warmer soon? She knew logically that winter wouldn’t last forever, but sometimes it seemed like it would.

Her car was still warm, which was a small blessing. But of course these smoothies were going to melt if she blasted her heat. Feeling ridiculous, she opened her windows and the same sharp wind came in, protecting the smoothies somewhat at the cost of her own comfort. Luckily, they were only going a few streets over from the shop. They weren’t going to melt during that time and Cleo wasn’t going to freeze.

Her destination was a tall old building that had been converted into a few apartments. Cleo grabbed her bag and walked up to the door, ringing the buzzer.

Nobody answered. She stood there for a moment on the stoop, holding the cold bag in her stiff hand. A new order pinged on her phone and she grabbed it, swiping to claim the order before looking at where it was going. Then she rang the bell again.

Again, nothing. Cleo stood there, feeling like an asshole and well aware of the fact that time and money were ticking away. She was about to ring it one more time when there were footsteps behind the door. Then it opened, and a man nodded at her. He didn’t say a word as she handed him the bag, just stepped inside and closed the door again, inches from her face. The flash of anger warmed her as she considered kicking his flower pot off the stairs. But she just went back toward the car, marking the order as complete. Then her phone buzzed again.


WTF. Tell me you’re not drinking those

Cleo snickered, then opened her delivery app to see what she’d claimed. And now she was going back to that same smoothie shop. With a sigh, she got in the car, not bothering to close the windows, and began driving right back down the road.

Three more smoothie orders and three more blank-faced customers later, she was ready to take a break. She’d earned just about everything she needed to for this shift and it hadn’t taken as long as she’d thought it would. But Edie was at rehearsal tonight and Cleo didn’t have any other plans, so she might as well earn a little extra money before driving all the way home. And despite the annoyances of this shift, she was reluctant to leave Boston right away when she’d just gotten back.

The Blossom Step were going ahead with their tour at the beginning of the summer. Cleo was glad about that, though both the fact that she wasn’t going, and that Edie would be gone for a month and a half hurt too much to think too hard about right now. But they’d gotten the same boost to their music from Cleo’s song going oddly viral over the past few months. They deserved to take advantage of that. She hadn’t talked about it, not since her recent, awkward, not quite fight, not quite lecture from Ryan, their lead singer, when she said she couldn’t leave her mother behind to go. She hadn’t even had the heart to bring it up to Edie since then.

God, why did Cleo care so much what all these people thought of her? She was good, she knew she was. And apparently thousands of people on the internet agreed with her. But the minute she ran into an argument like that or an iffy review (thank God it had been a while since one of those)? Poor Andrew had spent countless hours trying to cheer her up after Regional Underground had its say more than once.

But with Ryan, it felt personal. And partially because he had a point. Even if she managed to get this album written and recorded while the hype was still going, it wasn’t the same. And she knew in equal measure that she couldn’t go on this tour and that missing the tour would negatively impact her career.

But going would negatively impact her mother. And the memory of that back door swinging open and unattended was far too fresh in her mind for Cleo to even think about leaving Massachusetts. Even with her dad back, which was its own weird thing to think about. But he and her mother seemed happy, and he apparently had business in the area that he wasn’t discussing with any of them. So between Cleo, her dad, Tara Stevenson, and the occasional caretaker they could afford through insurance, they were covered.

Plus, Liv was still cooking enough meals that Cleo had finally insisted on covering all the groceries, not just the ones she managed to get on her own. And Noah and Andrew were around, though having strange men in the house stressed her mother out. Cleo wasn’t about to try to remind her mom that she’d known them for about twenty years – closer to thirty in Noah’s case. It would only stress her out further.

Another order came through, this one at a pizza place in Dorchester. Looking at the map, Cleo saw it was a few streets away from her old apartment. The fact that it was also a thirty-minute drive for eight dollars made it easier to justify rejecting it. Never mind, she was going to go home.


Her phone chirped as she was pulling into the parking lot outside her and Edie’s apartment about an hour later. It was the sound of a keyword alert. Cleo had keyword alerts set up for everything that could possibly be connected with her music. She’d had them for years, ever since a music industry professor had recommended they keep tabs on their publicity. Normally there were very few that were actually relevant. Mostly they involved other Cleos, other Rodriguezes, or some variation on her album names. Occasionally they included a local blog mention or a show listing, but that had been it for a long time.

Not anymore. Now her alerts were full of videos containing her song “Pull You Back”, or message boards where people were looking for ways to buy it, stream it, or steal it. At first this had made her uneasy, like it shouldn’t be happening to her. But it was exciting, peeking into people’s thoughts on her work. And some of these videos were fantastic, though she knew she was playing with fire, watching and reading all of these alerts. She got out of the car and started for the front door, opening the notification on her phone.

Boston’s Own Cleo Rodriguez: TikTok Celebrity?

She clicked on the link and her heart sank as the Regional Underground logo loaded at the top of the page. Leo Ravesi was apparently still following her career.

Anyone who’s only been to a show in Boston over the past six months might not recognize Cleo by face. She’s been a bit busy with the high life to embrace her hometown roots. But those talented chops that have graced Boston for nearly a decade seem to have found a new home on social media. If you’re under the age of twenty-five, or just want to be, then you’ve probably heard her song Pull You Back six or seven hundred times by now. Soundtracking prom dates, college acceptances, and amateur movies, the song showcases Cleo’s powerful singing chops. However, the lyrics echo their usage: juvenile and angsty in a way that doesn’t fit an older woman like Cleo. Hopefully, the money is worth selling her soul.

Cleo let out a breath, trying to stop the churning in her stomach as she got into her apartment. She could hear Andrew’s voice in her ear, mocking Ravesi the way he always had. But Andrew wasn’t here, and she was standing in her apartment alone, feeling cold in a way that had nothing to do with the winter weather outside.

Why did she let this asshole bother her so much? And what had she ever done to him? She thought back to their encounters throughout Boston in her twenties. Ravesi had been a few years younger than her and Andrew and she’d seen him at parties. Had he hit on her and she didn’t notice? Did he just hate her? Or maybe he was right, and she just sucked.

No. No, that was stupid. But she was already going for the call button on her phone and it was ringing.

“Hey,” Andrew greeted her a few seconds later.

He sounded like he’d just woken up although it was only seven. “Did I wake you?” Cleo asked. “I’m so sorry.”

“It’s fine,” he said. “We’ve been cleaning up the Limerick place, and I fell asleep for a bit when I got home. I’m actually meeting Iris in a little while, so it’s a good thing you called. What’s up, are you alright?”

“I’m fine, it’s stupid. I’m just-I got a bad review that shook me a little, that’s all.”

Andrew was quiet for a second. “I don’t suppose I know who it was,” he said finally.

“Regional Underground,” she said.

“Of course it was.”

“He said the song was angsty and juvenile, which I don’t really care about. But do you think I’m selling out?”

She felt a pang of déjà vu. They’d had this conversation last time Ravesi had trashed her in public. Right before they’d gone back to New Winslow for what was supposed to be a week.

“No, you’re not selling out,” Andrew said through a yawn. “He’s a prick, we’ve established that.”

“But maybe I’m selling out by trying so hard to make money with it,” she said. “I said a lot of things in that song and…”

“And it is an excellent song,” Andrew said. “And Ravesi is awful, as we well know.”


“Are you alright?”

She took a deep breath and let it out. “Yeah,” she said finally. “I think so.”

“Ignore him,” Andrew said firmly. “As I’ve told you every single time that little weasel writes something about you. His fixation on women isn’t healthy. Have you read the rest of his blog? The men get sparkling reviews, the women don’t. It’s a proper nightmare. Don’t give him any more of your energy.”

She nodded even though he couldn’t see her. “You’re right.”


Cleo laughed and settled back on the couch. “So how are you doing?” she asked.

He laughed, then yawned again. “Oh, where to start…”

After a little while talking to Andrew about everything except her career, Cleo felt better. She hung up and noticed that a text had come in while they’d been talking.


Hey Cleo. Just following up on our last meeting. Are there any other contracts you wanted to discuss?

The contracts for licensing her music. Not just the song Ravesi had dismissed, but others that had been found and brought to light as a result of that song. It was money, and she needed money. But maybe she was selling her soul? Maybe despite everything Andrew and The Blossom Step told her, she was selling out.

God, why did he get under her skin like this? There weren’t many local music writers, but the others had never gotten quite as fixated on her. So why him?

Either way, she’d wait a little while to answer Jude.


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