Love & Marriage in a Flash: My Sweet Strategist

I must have told my best friend to dump him a thousand times. In the end, I was the one drinking champagne at their wedding.
On the day of the wedding, I sat at the head table with the groom's chief strategist, auditing the damages on our phones.
Turns out, every time those two had a meltdown, we were the collateral damage.
Our chat histories were eerily identical.
[It's over. For real this time.]
[But what am I supposed to do? I can't stop thinking about him/her.]
The Groom's Strategist: [Get a new job. The circus is hiring clowns.]
Me: [You owe me emotional damages.]

1
I must have told my best friend to break up with him a thousand times. In the end, I was the one drinking champagne at their wedding.
The day the news dropped, my heart was a placid lake as I let out a hollow laughthe kind youd expect from a jaded queen in an old tragedy.
But as Grace Evans ride-or-die since we were kids, I showed up. I was her maid of honor, after all. I even came bearing a hefty check and a lavish wedding gift.
It was a joyous occasion, but I couldn't crack a smile.
Finally, Grace looked at me, her brow furrowed with concern. "Tracy, if you can't smile, don't. You look cool and mysterious with a straight face anyway."
"..."
Fine. My best friend might be a hopeless romantic, but she was marrying into a family whose net worth had more commas than a grammar textbook. Plus, she still loved me.
I could tolerate it.
When the groom's party arrived, I noticed one of the groomsmen looked even more miserable than I did. He seemed to fundamentally disapprove of this marriage.
He was handsome, though, in a completely different way from the groom. A single black stud gleamed in his left earlobe, accentuating his sharp, sculpted features. He had a roguish charm, and the tailored suit added a layer of dangerous sophistication.
One of the other bridesmaids noticed him and whispered to Grace, asking who he was.
And then I heard the name that had been a curse word in my vocabulary for years: Caleb Vance.
Just as I was Grace's best friend, this Caleb Vance was apparently the groom, Liam Foster's, childhood confidant.
For the longest time, I had harbored a bone-deep hatred for this man Id never met, a hatred second only to my feelings for Liam himself. Because every time I thought those two were finally done for good, this damned Caleb would whisper some brilliant strategy into his friends ear, and that dog Liam would somehow win my best friend back.
He was the master strategist behind their reunion. This wedding should have been his ultimate victory.
So why the long face?
Was he trying to provoke me?

2
While the bride and groom were grinning like absolute fools, Caleb and I stood there, our faces frozen masks of indifference.
After what felt like an eternity of ceremonies, I finally found my seat at the main table. I don't know if the seating planner was a chaos agent, but Caleb was seated right next to me.
The air buzzed with cheerful chatter, but a bubble of silence surrounded the two of us. We could have been mutes.
I watched him idly swipe through his phone before he turned his head, his gaze locking directly onto mine. Normally, when strangers make eye contact, one of them looks away after a second or two. This man did not look away.
Okay?
I was now certain he was challenging me. So I held his gaze, refusing to back down.
After a long moment, amidst the lively din of the reception, I heard his low voice. "Ms. Shaw. I've heard a lot about you."
So, he knew who I was.
I offered a smile that didn't reach my eyes. "Mr. Vance. A pleasure."
But that wasnt enough to convey years of pent-up frustration. I added, my voice dripping with sarcasm, "This day wouldn't have been possible without you. Your contribution has been... invaluable."
A slight frown creased his brow. "Thank you. The same could be said for you."
I scoffed. "Oh, I don't think we're quite the same. If Grace and Liam's relationship was a road full of bumps, I was the pothole."
God knows when I started trying to break them up. From the moment they were just flirting, I knew Liam was wrong for her. And sure enough, their five years together were a dizzying rollercoaster of breakups and makeups. I don't know if they were exhausted, but the drama was enough to make me swear off men for life.
Dating? Id rather adopt a dog.
A few seconds later, Caleb replied, "Then I must have been the roadblock."
"Huh?" I turned to face him again. "Weren't you the one always pushing for them to get back together?"
"Who told you that?"
Something wasn't adding up. I narrowed my eyes. "If you weren't his master strategist, then why did Liam always come crawling back right when they were on the verge of a real breakup?"

3
Caleb looked genuinely offended.
He unlocked his phone, scrolled back about three months, and angled the screen toward me.
Liam: [Bro, this might be it for real. I'm done with that heartless woman!]
Caleb hadn't replied.
Two hours later
Liam: [Bro, she said yes! (Grinning emoji)]
Liam: [Congratulate me, I'm getting married!]
Caleb: [?]
Caleb: [Have fun being her lapdog for the rest of your life. She tugs the leash, you bark.]
Caleb: [You were born a man, but you're choosing to live like a poodle. Stay close to your master.]
Liam: [Are you just jealous I'm getting a wife?]
...
Caleb looked at me, his expression deadpan. "Do you have any idea how close I was to having an aneurysm? They cry breakup at every little thing. Who knows if they won't cry divorce next? I'm doomed to be tortured by these two for the rest of my life. Do you understand my despair?"
Silently, I opened my own phone and found my chat with Grace from that same day.
Grace: [Tracy, I broke up with him.]
Me: [For how many days this time?]
Grace: [No, this time it's for real! I'm completely over him!]
I replied with a single, skeptical emoji.
Two hours later
Grace: [Tracy, I have to tell you something. Please don't be mad.]
Me: [You got back together?]
Grace: [He proposed! (Shy emoji)]
Grace: [I said yes.]
I said quietly, "I felt my world collapse."
Caleb stared at me. "...So you were trying to break them up?"
"You were too?"
Our eyes met, and a silent, horrified understanding passed between us. We started comparing notes, scrolling through our phones like two auditors examining a fraudulent account.
And we discovered that history was alarmingly consistent.

4
Liam: [We broke up. For real this time.]
Liam: [But what do I do? I can't get her out of my head.]
Caleb: [Listen to me. Get a new job. The circus is hiring clowns.]
Grace: [Tracy, I'm really done with him this time.]
Grace: [But I can't sleep. I just keep thinking about him.]
Me: [You owe me emotional damages.]
Grace: Wire Transfer - $520.00
I tolerated it.
Calebs voice was laced with disbelief. "Why does your best friend compensate you for her breakup drama?"
"Your buddy doesn't?"
Caleb fell into a profound silence.
As I scrolled further, I realized just how vicious Calebs texts could be.
Liam: [Thinking about my ex. What should I do?]
Caleb: [Go stand on your balcony.]
Liam: [What? Did you tell Grace to come see me?]
Caleb: [Let the cold wind clear your head. If an hour doesn't work, try all night. If that doesn't work, just jump.]
Liam: [I looked it up. Capricorns are just slow to warm up.]
Liam: [That's why it's taking so long to win her over.]
Caleb: [What celestial sin did we Capricorns commit to be slandered by you like this?]
Liam: [I sent her this huge paragraph. Why isn't she replying?]
Liam: [screenshot.jpg]
Caleb: [All I see is a wall of text memorializing your dead dignity.]
...
Then, a look at my own chats
Grace: [I broke up with him. His parents are setting him up with someone from a 'good family.']
Grace: [I'm done with love forever.]
Me: [Okay.]
Grace: [I'm in love again!]
Me: [New guy?]
Grace: [It's still him.]
Me: [Respect. Blessings. May you be locked together for eternity.]
Grace: [He forgot our anniversary. He obviously doesn't love me anymore.]
Me: [People get forgetful when they get older. It's normal.]
Grace: [He's not old! He's my age!]
Me: [A man is basically 60 after he turns 25. Trust me, find someone younger.]
Grace: [But he's... he's still so good to me. (Shy emoji)]
...
Looking back, it seemed Caleb had actually tried to be supportive at first. It was only after years of this torture that he turned into this venomous, cynical wreck.
There were countless chats just like these. But through the years, neither my efforts nor Caleb's acid tongue could permanently sever the bond between those two.
The power of a love-addled brain was truly terrifying. One was bad enough, but this was a case of two.
Caleb and I locked eyes again. This time, we saw the same shared misery reflected in each other's souls.
"Bro," I said.
"Sis," he replied.
It was time to formalize our alliance.

5
Two souls, united by shared suffering, exchanged contact information.
Caleb's voice was weary, aged beyond his years. "How long do you give them?"
My face was numb. "I'm hoping for a month."
We talked for a long time, our conversation drifting from the newlyweds to our own lives and work.
"You work at the Innovatech Campus too?" he asked, surprised.
I blinked. "Too?"
"I just got transferred back there. I'll take you out for dinner sometime, sis."

6
On the first workday after the wedding, Caleb made good on his promise.
Caleb: [Sis, your bro is here to deliver. Dinner tonight?]
I felt a slight twitch at the word "sis."
Me: [Bro, you promised. Your treat.]
Caleb: [Don't worry, your bro's got money.]
Satisfied, I put my phone away.
After work, I waited for him downstairs. A sleek black Mercedes G-Wagon pulled up to the curb, and the window rolled down to reveal Caleb's aggressively handsome face. He wasn't in a suit today, but a black technical jacket. The stud in his ear caught the last rays of the setting sun, glinting softly.
He looked even more roguish.
"Get in. I know a great spot."
I slid into the passenger seat.
He took me to a hidden gem of a restaurant, tucked away on a quiet side street. The ambiance was serene, the food was divine.
I dug in, and Caleb poured me a cup of tea from across the table. "Slow down. No one's going to steal it from you."
I mumbled an affirmative through a mouthful of food.
Halfway through the meal, my phone rang. It was Grace. My heart skipped a beat, a familiar sense of dread washing over me.
Sure enough, the moment I answered, her tearful voice came through the line. "Tracy, I don't think Liam loves me anymore!"
"..." I shot a look at Caleb, who returned it with an expression that said, I know that tone.
"It's been, what, three days, my dear sister?" I hissed into the phone. "Did you have a fight on your honeymoon?"
"No, we haven't even gone on our honeymoon yet."
"Then what is it now?"
"He said he was working late tonight on a huge project. But I was just scrolling through my feed and saw a picture his coworker posted. They're out for a team-building event! They're at a karaoke bar!"
"He lied to me! He doesn't care about me at all!"
I took a deep breath, feeling my blood pressure spike. "Is it possible that they finished the project and are celebrating?"
"No way! He just doesn't love me anymore!"
As I was racking my brain for a way to calm her down, Caleb suddenly held his hand out to me. I paused, then handed him my phone.
Caleb cleared his throat and spoke into the phone in a calm, authoritative voice. "Grace, hello. This is Caleb Vance."
The other end of the line went dead silent.
"Liam's project tonight? I was in charge of it. We just wrapped up," he continued smoothly. "My team has been killing themselves over this for the past two weeks. I'm treating them tonight, on my dime. I picked the place. Liam didn't even want to come, I had to drag him here."
"He didn't give you the details because he didn't want you to worry. That was his mistake. But I can personally guarantee you, he is absolutely devoted to you."
"If you don't believe me, I can put him on the phone right now."
After a few seconds of silence, Grace's small voice came through. "N-no, that's okay, Caleb. I'm sorry, I misunderstood. I hope you guys have fun."
The call ended.
I stared at Caleb, dumbfounded. "Bro, with skills like that... you're wasted in tech. You should be in PR."
Caleb handed my phone back, his expression unreadable. "You get used to it."
"I did this all the time when they were dating. Standard procedure."
"Calm one party down, then give the other an easy way out."
"What else are we supposed to do? Let them actually tear their lives apart?"
I suddenly realized he was even more of a long-suffering parent than I was.
Just then, Caleb's phone buzzed. He glanced at the caller ID, answered it on speaker with a deadpan look.
It was Liam.
"Bro! Help me!" Liam's panicked voice yelled. "I think my wife is mad at me! She's not answering my texts!"
"I think she's going to ask for a divorce!"
Caleb said, "Leave the karaoke bar right now. Go to the nearest flower shop and buy a bouquet of roses. Then go to a bakery and get her favorite strawberry shortcake. Then go home and get on your knees."
Liam was confused. "Huh? Why?"
Caleb's voice was dangerously calm. "Because when your wife called in a panic, I, in an effort to cover for your sorry ass, told her that I was in charge of your project tonight."
"And I," he paused for effect, "am currently having dinner with your wife's best friend, Ms. Tracy Shaw."
Silence from Liam's end. A full thirty seconds of it.
Then, his voice, now filled with a strange mix of terror and gossip-fueled excitement, whispered, "Whoa. Bro, are you... hooking up with my wife's maid of honor?"
A vein pulsed in Caleb's temple.
"Get lost."
He hung up and looked at me, exhaustion etched into his features. "See? This is our life."
I nodded in solemn solidarity. "You've worked hard, bro."
This meal felt less like a date and more like a strategy session between two war-weary veterans.

7
After that night, Caleb and I started talking a lot more. Since we worked in the same tech park, we often met up for lunch. His company's cafeteria was amazing, and I shamelessly mooched off him several times.
Before long, it seemed like everyone in his office knew who I was. One time, when I went to find him, the receptionist greeted me with a knowing, teasing smile. "Ms. Shaw! Here to see Director Vance again?"
"He's in a meeting, but you can wait in his office."
The title "Director Vance" threw me. I always assumed he was just another programmer from a wealthy family, like Liam. I had no idea he was an executive.
I sat in his spacious office, looking around. The decor matched his personalitya cool, minimalist palette of black, white, and grey. But there were touches of something else. A complex LEGO spaceship sat on his desk. A row of anime figurines lined a shelf. It was a fascinating contrast to his roguish, handsome face.
Just as I was admiring the collection, Caleb walked in. He shrugged off his suit jacket, tossing it casually over the back of his chair, and loosened his tie. "Been waiting long?"
"Nope, just got here." I put my hands together in a mock martial arts bow. "Director Vance. I am not worthy."
He chuckled, the corners of his eyes crinkling. "Stop messing around."
"Got plans tonight? If not, dinner's on me."
"Sure. It's my turn to pay. Can't have you going broke on my account."
"Deal."
He walked over and, in a gesture that felt surprisingly natural, ruffled my hair. "What are you in the mood for?"
My heart skipped a beat.
The gesture was so intimate. I could smell the faint, woody scent of his cologne. I turned my head away, feeling a blush creep up my neck. "Anything... anything's fine."
Caleb seemed to realize it too. He retracted his hand, clearing his throat. "How about that hidden spot from last time?"
"Sounds good."
The atmosphere had suddenly become charged, a delicate tension hanging in the air. Neither of us spoke.
The spell was broken by Grace's frantic phone call.
"Tracy! I'm pregnant!"
"...?!"
I glanced at Caleb. He'd clearly heard. The look of sheer panic on his face mirrored my own. I shakily put the call on speaker. "Grace, are you serious?"
"Of course! Two lines on the pregnancy test! I just took it!"
"I haven't even told Liam yet! You're the first person I called!"
"What do I do now, Tracy?! I'm so nervous! I'm not ready to be a mom!"
Before I could even process the information, Caleb spoke, his voice a beacon of calm in the storm. "First, go to a doctor and get a proper confirmation."
"Second, tell Liam."
"Third, take a deep breath and try not to spiral."
Grace's voice was timid on the other end. "C-Caleb? Why are you there?"
"I'm with Tracy," he said simply.
"...Oh."
That single "oh" was loaded with a universe of meaning. I could practically feel her gossip-loving heart combusting with curiosity.
After the call, Caleb and I just stared at each other.
"Those two," I sighed. "As long as they're breathing, they'll find a way to create chaos."
Caleb rubbed his temples. "Come on, let's get dinner."
"After that, I'll take you to the hospital."
I blinked. "Why am I going to the hospital?"
"Your best friend is pregnant. Aren't you going to be there for her?" he asked, as if it were the most obvious thing in the world. "She's probably a nervous wreck, and we both know Liam is useless in a crisis."
"You go keep an eye on things. It'll put my mind at ease."
A warmth spread through my chest. This guy, for all his cold and cynical posturing, was incredibly thoughtful.

8
I went with Grace to her appointment, and the pregnancy was confirmed. When Liam heard the news, he hugged Grace, laughing and crying like a fool. Infected by his emotions, she started crying too. I watched them from the side, a mix of amusement and genuine affection swelling inside me.
These two lovebirds, as exhausting as they were, truly loved each other.
It was late by the time we left the hospital. Caleb had been waiting for me by the entrance the whole time. When he saw me, he handed me a warm cup of hot chocolate.
"You've had a long night."
"It was fine. I'm just a little hungry."
"Get in. Let's get you some food."
Soft music played in the car. I held the warm drink in my hands, watching the city lights blur past the window, and a sudden sense of peace washed over me.
"Caleb."
"Hmm?"
"What are we?"
I don't know why I asked. Maybe it was the gentle mood of the night, or maybe being around the happy, chaotic couple had stirred something in me.
Caleb's hands tightened on the steering wheel for a fraction of a second. He turned to look at me, the glow of the streetlights softening the sharp lines of his face.
"What do you think we are?" he asked back.
"Siblings from another mother?" I ventured.
He laughed. "Tracy, are you an idiot?"
"We're two single adults who met through mutual friends, who seem to get along pretty well, and who enjoy spending time together."
"You call that being siblings?"
My face grew hot. "Then what do you call it?"

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