The Double Contract Girlfriend

The Second Offer

RILEY

I didn't even want to go out tonight.

After I got that glossy white envelope with Thirty Thousand Dollars inside, I'd spent the past two days staring at it like it was some kind of cursed treasure. Who just… hands out that kind of money? And for something as bizarre as "meeting her son"? It felt shady, transactional, and a little insulting. But the money was sitting pretty in my bank account now, and I'd already told myself I'd at least follow through, for appearances.

Tara was the voice I needed to feel better when I feel guilty. She had a knack for doing wild and outrageous things, quite the opposite of me who had less guts. I could tell how proud she was when I told her about taking the offer, she felt i was finally getting some nerves to make daring moves. I couldn't help but still feel guilty, when she dragged me to this expensive bar downtown, she promised it would be "good for my nerves."

The music was loud enough to drown out my thoughts. We'd claimed a corner table, and she was halfway through her second martini while telling me about some guy who texted her after ghosting for a month. I nodded at the right moments, my mind elsewhere, tracing the lip of my glass with one finger.

Then, I felt it. That shift in the air when someone's looking at you. I glanced up and caught sight of him.

Tall. Dark hair that looked like it had been styled carelessly but still managed to fall perfectly into place. A charcoal suit jacket over an open-collared shirt. He wasn't leaning against the bar like he owned it, but the way the bartender kept checking on him made me think he might as well.

And he was looking at me.

Not in that crude, undressing-you-with-his-eyes kind of way, but like… sizing me up. Judging. Deciding. I was tempted to look over my shoulder to see if there was someone else behind me, but his gaze was steady, pinned to mine like he'd made up his mind about something.

Tara followed my glance and smirked. "Uh-oh. Mr. Tall, dark, and Expensive is making a move."

"I doubt it," I muttered, taking a sip of my drink. But even as I said it, he pushed away from the bar and started walking toward us.

CHANDLER

She didn't belong here.

Not in the sense that she looked out of place, quite the opposite. She made the dimly lit bar look like it was designed around her. The warm gold light caught in her hair. Her dress was elegant but effortless, not screaming for attention, just… right.

The second I noticed her, I thought, She's exactly the type mother would like.

And that was the problem.

Mother had been on my case for months about "meeting the right kind of woman." She had a list. Yes, an actual list, of potential candidates, complete with résumés and family histories like she was hiring for a corporate position. I'd managed to dodge every one of her setups so far. But this girl?

She was too perfect in exactly the way mother liked. Which gave me an idea.

If I showed up to the next dinner with someone like her on my arm, I could end this matchmaking circus. My mother would believe I'd finally chosen someone, on my own terms. And if I made it clear it was serious, she'd drop the rest of her "options."

I walked toward her table, every step confirming I was right about her. She looked up at me, guarded but curious. The friend at her side leaned back, already grinning like she knew where this was going.

"Hi," I said simply. "Can I sit?"

She glanced at her friend, who shrugged and stood up to leave. "Uh… sure? I was about to head to the restroom, anyway"

I slid into the seat across from her. "I'll get straight to the point. I'm not here to ask you out. Not… exactly."

Her eyebrows rose. "That's one way to start."

"I need someone to pretend to be my girlfriend," I said. No hesitation, no sugarcoating. "It's… a family thing. I'll pay you for your time, and I'm not talking about dinner and drinks money. It's gonna be a proper arrangement. A few appearances, some handholding, maybe a kiss in public now and then if it sells the story. But no strings beyond that."

She didn't speak right away, just blinked at me. "You're serious?"

"Completely." I leaned in, lowering my voice. "You're exactly the kind of woman my mother approves of. That's… part of the point. I want her to think I've already made my choice so she'll stop trying to set me up. You help me, I help you. Simple."

Her lips twitched like she was about to laugh, but then she tilted her head, studying me. "Other than the honor of fake dating a stranger, why is this an offer so great you'd expect me to jump right into it?"

I smiled faintly. "I can make it worth your while. Fifty thousand to start. More if this drags out longer than expected.

She stared at me like I'd just asked her to help bury a body.

The music in the bar thumped softly beneath the low murmur of conversations and clinking glasses, but somehow the silence between us still felt louder.

"Fifty thousand?" she repeated carefully.

I leaned back against the booth like I had all the time in the world. "You heard me."

Her fingers tightened around the stem of her drink. Too much ice. She didn't look like the kind of woman who spent nights in places like this regularly. Her dress was pretty but simple, black fabric hugging curves she probably wasn't even trying to show off. No designer labels. No diamonds.

Ordinary.

Which was another reason why I picked her.

No socialite connections. No ambitions to climb through my family. No rehearsed flirtation the way women usually approached me once they knew my last name. Just a woman trying to enjoy a drink before I interrupted her evening.

"You want me to pretend to be your girlfriend," she said slowly, like she still couldn't believe the conversation was real.

"For a few weeks."

"And you're offering fifty thousand dollars?"

"Yes."

She blinked twice.

I almost smiled.

Most people tried to hide the effect money had on them. Shock first. Temptation second. Then came the internal bargaining, where pride fought greed for a few pathetic minutes before greed usually won.

I was patient enough to wait for it.

"What's the catch?" she asked again.

"No catch."

"That's bullshit."

That nearly made me laugh.

I tilted my head slightly. "You'd attend a few dinners with me. Pretend to like me in front of my mother. Act convincing enough that she stops setting me up with daughters of her rich friends. That's it."

"That's it," she echoed skeptically.

"Yes."

She studied me carefully now.

I was used to that look too.

Women trying to figure out whether I was dangerous, arrogant, or insane.

Usually all three.

"You don't look desperate enough to pay someone fifty grand."

"I'm not desperate," I said smoothly. "I'm inconvenienced."

That earned me a tiny smile.

There it was.

The first crack.

I watched her take another sip of her drink while pretending not to think too hard about the offer. But I could already see the shift in her posture. The hesitation weakening. Curiosity replacing suspicion.

People liked pretending they couldn't be bought. Everyone had a number.

"What exactly would I have to do?" she asked.

I slid my phone across the table toward her. "Like I said, all you have to do is make public appearances with me. Hold my hand a few times. Laugh at one or two jokes. Look at me like you tolerate my existence. Then we have dinner with my mother, which is the most important. I'm looking to impress her more than any other person."

"Tolerate?" she repeated.

"You're not required to be convincing enough to deserve an Oscar."

She laughed softly this time, and I noticed how quickly she tried to hide it.

Cute.

Not stunning. Not breathtaking. But real enough to be believable.

My mother would love that.

"What if your mom asks questions?"

"She will."

"And?"

"You answer them."

"You're making this sound easy."

"It is easy."

For me, anyway.

She exhaled through her nose and glanced around the bar, buying herself time. I let her think. Let her wrestle with the morality of accepting money from a stranger for a fake relationship.

Meanwhile, I already knew how this would end.

The thing about wealth was that eventually it stopped feeling like money and started feeling like leverage. Influence. Control. A tool that bent situations into whatever shape I needed.

And tonight, it was bending her.

"You're rich rich," she said before she could stop herself.

I smirked faintly. "I appreciate the reminder."

She shook her head once, almost laughing at herself now.

"You seriously walk around bars asking random women to date you for money?"

"No. You're the first."

That part was true.

Because unlike the polished women at charity galas or corporate events, she hadn't approached me all night. Hadn't stared too long. Hadn't adjusted her dress when I walked in.

She didn't care who I was until I made her care.

Which made her useful.

Her fingers tapped lightly against her glass before she finally looked up at me again.

"Fifty thousand upfront?"

I almost smiled at how quickly the conversation shifted once she started considering the deal seriously.

"Half upfront," I said. "Half when we're done."

"And if I say no after tomorrow night?"

"Then you keep the first half."

Her brows lifted.

I could practically see the moment greed finally strangled caution.

Then she nodded once.

"Okay," she said quietly. "I'll do it."

There it was.

Acceptance always came with that tiny pause beforehand. That last fragile second where people convinced themselves they still had dignity while selling a piece of themselves.

I kept my expression calm, controlled, unaffected.

But internally?

I was already satisfied.

Because I knew from the second I sat across from her that she'd say yes eventually.

Money always worked.

And deep down, I think part of me enjoyed proving it.

RILEY

If there's a heaven for opportunity, I'd just earned my halo.

I tried to keep my face neutral, but inside, my thoughts were cartwheeling. Sloane had paid me thirty grand to meet her son. Now this stranger at the bar is offering me fifty grand more to pretend to be his girlfriend. Well, what's better than thirty grand? You guessed right! Fifty grand more… all for what? Dressing nicely and smiling at dinners? I just might have found a new line of job

I should've felt gross. I did feel a little gross. But mostly, I felt like I'd stumbled into the jackpot of easy money.

I leaned back in my seat. "You've got yourself a deal."

He handed me his business card.

"Meet me here on Friday, so we can discuss the terms in full. By the way you'll need a makeover for a charity luncheon I'm attending, That's where we'll make our debut." shook my hand firmly, like we'd just closed a business contract.

"Friday," I repeated. "Got it."

As he walked away, I couldn't help smiling to myself. Easy money. No strings. I'm beginning to like these opportunities life has been throwing at me.

Tara got back just as he was leaving

"Don't tell me you blew this off" she asked, already disappointed.

"You would not believe what just happened”