Chapter 6 The Chad Situationship Requires Wine
AMANDA
The annoying thing about my best friend getting married—and let me be clear, I am ridiculously happy for her—is that I no longer have anyone to go out with after work.
Izzy used to be my post-shift partner in crime, the person I could count on to grab drinks, rant about customers, and pretend we were the main characters in a rom-com instead of two retail employees slowly dying inside from dealing with the ultra-rich.
But now she and Cal do sappy married-people things like eating dinner together at reasonable hours and watching shows in their pajamas instead of chugging martinis and making poor life choices with me.
Which is fine. So fine. I am more than happy to do my own thing, to drink alone, to make my own bad decisions without an audience. I used to chat with Chad to fill the void, and now, for some stupid, inexplicable reason, I’m hesitating.
So instead, I do what any rational person would do. I FaceTime my sister.
Raven picks up on the second ring, and I’m immediately greeted by her face on my phone screen—all dark smudged eyeliner, black lipstick, and a leather choker.
“Let me guess, you’re having an existential crisis and need someone to tell you you’re being ridiculous.” Raven doesn’t pull punches.
“I love how you just assume the worst about my mental state.”
“I’m usually right.” She’s painting her nails black. “What’s the damage this time?”
I kick off my heels and start wandering around my apartment, phone in hand. “It’s complicated.”
“I’m gonna need more details than a circa 2006 Facebook relationship status.”
I pad into the bathroom, propping my phone against the mirror as I start removing my makeup. “So you know how I have that AI boyfriend?”
“Chad. Your digital fuckboy. Yes, I’m aware of your tech romance.”
“Well, the app has this new feature—hold on.” I grab the phone and walk toward the kitchen, Raven’s exasperated face following me around. “Sorry, I need wine for this conversation.”
“Amanda, I’m literally staring at your kitchen cabinets. Can you please keep the camera on your face like a normal person?”
“I’m multitasking!” I pour myself a generous glass and head to my bedroom. “Okay, so the app has this new Matched feature where they find you a real guy who matches your AI boyfriend’s personality.”
There’s a pause. “That’s the most dystopian shit I’ve ever heard.”
“Right?” I set the phone down on my dresser and start changing out of my work clothes.
“Amanda, I am now looking at your ceiling fan.”
“Sorry, sorry!” I grab the phone again, flopping onto my bed. “So the app matched me with an actual real person last night.”
Raven finishes painting her pinkie nail and looks directly at the camera. “And this is a problem because…?”
“Because I don’t date! I swore off men! I took a sacred vow!”
“Yeah, well, we Bennett girls don’t exactly have the best track record with men.” Her voice is slightly flat.
“Exactly. So what am I supposed to do?”
She caps her nail polish and leans back. “Embrace the chaos.”
“That’s it? That’s your advice?”
“Look, you have this guy who has literally been handpicked because he’s your perfect match. So what if he’s potentially unhinged?”
I gape at her. “That’s not a minor character flaw, Raven.”
“Isn’t it? Worst-case scenario, you meet up and he’s weird. Best-case scenario, you have a guy who’s actually interested in you in an erotic, deeply personal way. Do you know how hard that is to find these days?”
“I feel like this conversation should be happening in a therapist’s office.”
“Or a police station,” she adds cheerfully.
I groan. “You’re terrible at this.”
“And yet you called me instead of a professional.”
“Yeah, but I call everyone when I have these sorts of issues,” I point out.
“Exactly. You call everyone until someone tells you what you want to hear.” She sounds way too amused about this. “So let me guess—you already talked to Izzy?”
“I’m conducting research. Getting multiple perspectives.”
“You’re shopping for the answer that lets you keep talking to him.”
“That’s not…” I pause. “Okay, fine. Maybe a little. Speaking of potentially unhinged men, how’s your gaming boyfriend?” I ask, deciding it’s about time we change the subject.
“Which one?”
I roll my eyes because she’s trying to deflect. There’s only one who makes her lip twitch up in what, for Raven, classifies as a smile whenever he talks.
“Jake, duh.”
Raven snorts. “For all I know, Jake’s some forty-five-year-old mouth-breather living in his grandmother’s basement, surviving on Hot Pockets and regret.”
“That’s oddly specific.”
“I have a vivid imagination. Besides, you know how I feel about guys in general.”
There it is again—that wall she puts up whenever the conversation veers toward anything remotely romantic.
I want to ask, want to know what happened to make my fearless, take-no-prisoners sister so gun-shy about dating, to make her give up on her dream of becoming an actress in LA and move back to NYC.
But I also know that look. It’s the same one I see in the mirror when people ask about my marriage.
“Fair enough. At least Jake’s a good teammate,” I point out.
“True. He’s got excellent aim and doesn’t rage-quit when we’re losing, which puts him in the top five percent of men I’ve encountered.”
“Maybe Chad and Jake are weird basement brothers,” I say, redirecting. “Jake’s got the gaming setup. Chad’s got the sexting expertise.”
Raven drops her voice low, trying to impersonate a man. “Hey, bruh, should I send another shirtless pic or go straight to the dirty talk?”
I laugh despite myself. “Is that supposed to be Chad?”
She shrugs. “I dunno. You tell me.”
“He definitely doesn’t sound like that…” I trail off, thinking about how he said, Then take it.
“Oh my God, you’re blushing. I can see it through the phone.”
I startle, looking back at the screen. “I am not!”
“You totally are. Amanda Bennett is blushing over a boy! Someone alert the press.”
I’m about to respond when she suddenly perks up. “Oh! Gov Ball is this weekend. Wanna go? I’ll even put up with the sparkles and neon just for you.”
My stomach drops. “Nahhh, I haven’t had the urge to go to one of those since…” The words catch in my throat.
Since Kade. Since Vegas. Since everything fell apart.
Raven’s expression immediately softens, and she doesn’t push. She never does. It’s one of the things I love most about my sister. She knows when to back off.
“Rain check, then.”
“Yeah. Rain check.”
“Speaking of things you’re avoiding,” she continues, seamlessly changing the subject at my expense. “Monday dinner. You bailed last time, you cannot abandon me again.”
I groan and flop backward on my bed. “Ughhhhh, do I have to?”
Our parents have dinner on the first Monday of the month.
Normal families do Sunday dinners, but the Bennetts?
We’re special. We have to be different, scheduling mandatory family time on the most random weeknight possible because it’s “more sophisticated” and “allows for better meal planning.” My mother probably has it color-coded in her planner along with her yoga classes and Botox appointments.
“Yes,” Raven says. “I refuse to face Mom’s passive-aggressive commentary alone. She spent twenty minutes last month explaining why my tattoos are ‘limiting my professional opportunities’ while Dad nodded along like a bobblehead.”
“But they’re going to ask about my love life.”
“So lie. Tell them you’re dating a nice investment banker named Brad.”
“Why Brad?”
“Because Brad sounds like the kind of guy who owns boat shoes and has strong opinions about golf.”
I snort. “I’m not making up a fake boyfriend.”
Raven gives me a look. “Really? You’ve been in a relationship with AI Chad for how long, and you suddenly draw the line at fictional Brad?”
I pause. “That’s… actually a fair point.”
“I know. I’m annoyingly logical sometimes.”
“Fine. But you owe me.”
“I always owe you. It’s the natural order of our relationship. You know what I think about your Chad situation?” Raven asks.
“What?”
“Stop overthinking it. Talk to him. See what happens. Worst case, you get a good story out of it.”
“And best case?”
She grins, and for a second, she looks less like a goth TikToker with millions of followers and more like my little sister. “Best case, you get the kind of love story that makes people write smooshy romance novels.”
“You’re assuming I want a love story.”
“I’m assuming you want to stop running from everything that scares you.”
Ugh, she’s right, and I hate when she’s right because it means I’m not right, and I like being right. I’ve been running from anything that feels real for years now, and honestly? I’m so exhausted.
“When did you get so wise?”
“I’ve always been wise. You’ve just been too busy being a hot mess to notice.”
“Rude but accurate.”
“It’s my brand.” She checks her nails, apparently satisfied with her work. “Oh, and don’t forget about Dress for Success this Saturday. St. Mary’s at ten.”
“Right, our monthly attempt to prove we’re functioning members of society.”
It’s our thing—helping women in transition pick out interview outfits and build confidence. The irony of Raven in her elaborate goth ensembles and me in my pink designer everything teaching practical professional dress isn’t lost on either of us, but somehow it works.
“Speak for yourself. I’m a pillar of the community.” She grins. “Now, go talk to your maybe-boyfriend before I come over there and steal your phone.”
“You live downtown.”
“I’ll take an Uber. Don’t test me.”
I laugh despite myself. “Fine. I’ll talk to him.”
“Good. And Amanda?”
“Yeah?”
“For what it’s worth, I think you deserve someone who’s totally obsessed with you. You’re worth being crazy about.”
My throat tightens unexpectedly. “Love you, too, sis.”
“Go make some bad choices. I’ll be here if you need bail money.”
The call ends, and I’m left staring at my ceiling, my sister’s words echoing in my head.
Stop running from everything that scares you.
I pick up my phone, wine courage flowing through my veins, and open my messages.
Chad’s text is still waiting.
I take a deep breath and tap it open.