Season of Second Chances

9. Dating Bootcamp

“Hi Samantha. So how’s your weekend going?” Charlotte read aloud, raising a brow. “Not hugely original, but hey, it’s better than ‘hi.’ It’ll do for now.” Charlotte smirked and turned to Sam. “Now you are going to have a completely normal conversation and see where it goes. Easy, right? Ready to take the reins, madame?”

“I don’t know.” Sam rubbed her temples, already feeling the weight of her nerves. “Is there, like, an online dating manual or something I should read before diving into conversations with strangers?”

“It’s like small talk in real life, only easier, as you don’t have to fake smiling the whole time.” Charlotte grinned, her confidence infectious. “Keep it simple. Ask questions, get a feel for their vibe. And remember, fun is the keyword here, okay?”

Sam stared at the message like it held the weight of the world. “What do I even say? ‘Hi, I’m currently dismantling a ten-year relationship because my boyfriend wants to screw everyone else?’” She groaned, flopping back against the sofa with an exaggerated sigh, grabbing the remote. “See, I told you it was too early for this.” Her frustration hung heavy in the air.

“You know,” Charlotte said, her fingers flying over the keyboard, “you don’t have to spill your life story in one go. Just say you’re chilling with your bestie and eating pizza—which is both true and relatable. Then shift the focus to him. People love talking about themselves.”

“I need a timeout from all this insanity,” Sam said, scrolling through the movies available. “Can’t we just watch something mindless? I’m still recovering from last night’s chaos.” She sipped her soda, avoiding Charlotte’s laser sharp focus.

But Charlotte was in her element, fingers flying across the keyboard.

As the movie played, Sam melted into the cushions, stealing occasional glances at Charlotte, who was glued to the laptop like it was a thriller novel. By the time the credits rolled, Sam stretched with an audible c***k of her joints. “Wait… you’re still at it?” she asked, her tone equal parts disbelief and exhaustion.

“Oh, I absolutely am,” Charlotte replied with a mischievous grin. “Did you really think you’d get off that easily?” She spun the laptop toward Sam. “There are a few decent guys, and two already want to meet you. Sooo... buckle up—you’ve got dates next week!”

“You’ve completely lost your mind,” Sam said, shaking her head furiously. “I’m not ready for dates, Charlotte! I can barely manage this conversation!”

“You think you’re not, but trust me—once you’re out there, you’ll feel the spark again.” Charlotte held out her hand expectantly. “Now, hand over your phone.”

Sam sighed dramatically. “Why? Am I grounded?” she asked, though a faint laugh with a snort escaped her lips.

“I’ll install the apps so you can message these guys directly. You’ll need to figure out who you like. Although, it doesn’t quite matter right now. You just need to get out more and once you see how all these men wish to pursue you, it’ll do wonders for your confidence.”

“Isn’t this leading them on?”

“Maybe a little, but hey, they’ll survive.”

“You are a certified monster, Charlie.”

“Why, thank you, darling. I love you too.” She chuckled, then added, “So, how about hitting the gym with me tomorrow?”

“I don’t know… I feel like staying home in bed until the end of time. You do realize I’m still emotionally drained from the last twenty-four hours, right?”

“I know, Sam, but you’re young, beautiful, and you’ve missed out on so much. You’ve been in a serious relationship through your prime years. And honestly? I’ve missed us doing things together. Eric kind of took over your world…”

“And now you want to take over it?” Sam teased, only half-joking. She realized how much her friend missed her. Sure, they’d met up regularly, but Charlotte was right—Sam had spent the last ten years building a life with Eric and focusing on her career.

“Maybe just a little,” Charlotte admitted with a wink, still focused on Sam’s phone. “Okay, all done! Let me show you how this works. Swipe right if you like someone, left if you don’t. Simple enough, right?” She tapped on the messages tab. “Okay, so... the accountant—Jake—asked you to dinner. Solid option, if you ask me. Then there’s this IT guy who wants to meet for coffee. Personally? I’d skip the coffee dates.”

“Why?”

“Not enough effort, that’s why. Coffee dates scream ‘bare minimum.’ Sure, they’re fine for testing the waters, but if you’re looking for someone serious? Skip them.”

“I mean… isn’t it fair to start with a ‘bare minimum’ date? Especially if it ends up being the last?”

“That depends. Do you really want to spend two hours getting ready for a five-dollar coffee? Because let’s be real—it takes a guy ten minutes, max, to throw on jeans and a half-decent shirt. If it’s after work, fine, maybe you’re already dressed, but still—you’re the one putting in all the effort. Touch-ups take time!”

“Got it. Thanks for the dating TED Talk.”

“Anytime, bestie. Okay, so… Here are a couple of promising ones. Let’s see how their conversations pan out over the next few days.”

“I cannot believe it’s been so much action on here in just a few hours.” Sam’s voice was a mix of awe and exhaustion.

“And that’s me cutting out all the time-wasters. Trust me, it could’ve been way worse.” Charlotte stretched her arms overhead, letting out a big yawn. “Whew, this matchmaking business is exhausting. You’re lucky to have me.”

“I am indeed.” Sam couldn’t help but yawn in response. “Apparently, yawns are contagious,” she muttered, shooting Charlotte a half-smile.

“Okay, it’s getting late. Let me grab you some bedding and a towel.” Charlotte disappeared into her bedroom.

Sam stared at her phone, her expression caught between irritation and disbelief. How did things spiral to this point? Was it something she did—or didn’t do—that led to this mess? The questions looped endlessly in her mind, each one heavier than the last. She sighed, clutching the phone like it held answers she wasn’t ready to face.

Samantha stared blankly at the phone as doubt crept in, uninvited and unwelcome. Maybe she had jumped to conclusions. Maybe Eric’s proposal wasn’t as selfish as it had felt. Could they fix it? Could she? The questions left a bitter taste in her mouth, but a tiny flicker of hope threatened to ignite. She shook her head, trying to snuff it out. No. That ship had sailed, hadn’t it?

Charlotte reappeared, her arms full of bedding and a towel, snapping Sam out of her spiraling thoughts. ‘Maybe I’m a tad naive,’ Sam thought, biting her lip. ‘But even I know better than to hope for a miracle.’ She plastered on a small smile as Charlotte approached.

“Here we go—bedding, towel, PJs and the essentials,” Charlotte declared, dumping everything onto the makeshift bed with exaggerated flair. “Let me know if anything is missing.”

“Thanks, Charlie.” Sam gave her friend a genuine smile. “It would be less bearable without you, you know?”

“I know,” Charlotte replied, fluffing the pillow dramatically. “Come on, let’s get this set up.”

Together, they worked in sync, fluffing pillows and tucking corners, but Sam’s phone kept lighting up with notifications, each one tugging at her nerves. Charlotte caught her glancing at the screen. “You’re popular already, huh?” she teased.

Sam forced a laugh. “Yeah… popular,” she murmured, though the constant buzzing felt more like a relentless reminder of last night.

She glanced at the screen. A message lit up: ‘Hey Samantha, can't wait to meet you.’

Her stomach flipped. She groaned, tossing the phone aside. “How did this become my life?”

Charlotte smirked. “Better buckle up, Sam—it’s just getting started.”