The glow of the TV illuminated the room as the screen flicked through Tinder profiles for dramatic effect and a woman's voice narrated over the screen. Rory felt torn between the belief that it was time to put herself out there again and the impulse to shun dating forever and commit herself to a lifetime of solitude and a really good vibrator.

It was strange how even watching a horror story about online dating could make her feel like she was supposed to be dating. Why? So she could be catfished? Conned out of money she didn't even have? Coerced into sex and then dropped like a bead of water from a cumulous cloud?

But on the other hand, it would be nice to be romanced again. To feel the thrill of really connecting with someone for the first time. To have an actual life to look forward to.

The screen shifted to Cecile sitting at a restaurant table talking about their first date when Rory heard the door of the apartment open. Lane flicked on the light as she made her way through the threshold.

"Really?" Her best friend gave her a shrewd look as her gaze bounced back and forth between the TV screen and Rory, curled under the blanket munching on a Red Vine with her fuzzy sock clad toes sticking out from under the covers, bouncing involuntarily.

"What?" Rory asked, her voice innocent but her face looking like she'd just been caught watching hardcore porn.

"The Tinder Swindler again?"

Rory shrugged, trying to act nonchalant as she paused the television. "So what?"

"This wouldn't have anything to do with you trying to convince yourself that rich, charming, good-looking men are all evil crooks, would it?" Lane asked as she shut the door and plopped her overnight bag on the floor near the hallway.

"What?" Rory scoffed. "No." She always rewatched things. Lane loved to bust her chops for watching the same thing over and over and over again but it was what she did. Her and her Mom had always been that way. It was all the better for mocking the second time around. Of course, this was the sixth time around, but still…

"Uh huh," she nodded. "Likely story"

"Why would I need to convince myself of that?"

Lane plopped down on the couch next to her, grabbing a Red Vine off the coffee table. "To assure yourself you made the right decision turning your hunky boss down."

"I did make the right decision. And it's not even remotely the same thing. It's not like Logan asked me out on a date to a fancy, five-star restaurant to seduce me. It was a fake marriage proposal. And he's not trying to swindle me, he's very clearly a real multi-millionaire. He owns the company I work for and our families know each other."

"But you want him to…" Lane surmised, "ask you on a date. And there would be fancy dinners at five-star restaurants."

"No, I don't. And you know I don't care about fancy restaurants."

"I know," Lane nodded, taking a bite of her licorice. "But you do care about the dim lighting and yummy food and getting lost in deep conversation with a cute boy."

"None of which I'll be able to do with a guy I actually like if I'm fake married to my boss."

"But you could do it with Logan," Lane waggled her licorice stick at her. "And maybe, just maybe the two of you will accidentally fall head over heels for each other and live happily ever after."

Rory's eyes rolled dramatically. "That's not going to happen."

"Look, I know you like to read books written by wordy, dead, Russian dudes. But those of us who read things written in the twenty first century know that the fake relationship trope is so common that it's basically become its own genre. And the protagonists always fall in love by the end."

"This isn't a book, Lane." Rory shook her head. "This is real life. Logan and I don't even have anything in common."

"You have some things in common." Lane reminded her. "You both work in the same field. Your grandparents know his parents. You both went to ivy league schools," she ticked off on her fingers. "That's why he asked you…because you have things in common."

"No, he chose me because I'm safe. He said so himself. He wants someone that would just be a business partner. Someone to go through the motions with him without falling in love."

"Ahh," Lane relaxed back into the sofa, pulling her legs up underneath her. "And that's the problem, isn't it?" she asked with a sly smile and raised, teasing eyebrows. "Unrequited love." The words came out as a sing song and Rory knew that Lane was just busting her chops.

"Oh my god," Rory rolled her eyes and shook her head with a laugh. She picked up a throw pillow and chucked it at her friend playfully. "You are insane."

Lane laughed back and swatted the pillow away. "Well, that's not a secret."

"And you're deflecting—trying to take the focus off of you and your weekend with Dave," Rory pointed accusingly.

"Am not!" Lane huffed, crossing her arms over her chest. Now it was her turn to be under the hot light. She'd gone to Manhattan yesterday for her big date with Dave, with plans to tell him about her commitment to waiting until marriage to have sex. She'd been hesitant to go to the city for the weekend without him knowing the deal already, but she'd also felt it was important to tell him in person. So, not knowing how he'd take it, she'd packed an overnight bag just in case but had also been prepared for the date to end early, strictly memorizing the Metro North train schedule just in case she needed to make alternative travel plans. Rory had received a text late last night telling her not to expect her home that evening, with no other details. She assumed that meant things went well.

"Uh huh," Rory nodded mockingly. "Then tell me, Miss Kim, what exactly happened on your big overnight date?" She hoped Lane hadn't done anything she didn't want to do just to keep Dave around. She felt fairly confident that wasn't what happened, but she'd feel better once she heard Lane tell her.

"Nothing," Lane shrugged, shoving another Red Vine into her mouth.

"Likely story."

"No really, nothing," Lane insisted through a mouth full of corn syrup and red dye number 40. "I told him at dinner. I was a complete idiot about it, I swear. But I did it. And he was a complete gentleman. Like, seriously," her lips curled up into a dreamy smile and Rory's face couldn't help but follow. "I mean, he was disappointed, but he totally understood. He said he'd waited ten years to find his way back to me and he could wait as long as I needed. Then he slept on his couch and gave me the bed." See? This was what Rory wanted. The real deal. Someone to love her for who she was. Not some fake relationship where she had to pretend to be in love and watch a man pretend to love her. And sure, a real relationship was risky; there were some Tinder Swindler's out there, but there were also some Daves. And Rory couldn't give up the opportunity to find her Dave just to save her grandfather's business. She'd made the right decision. And maybe it really was time to dip her toe back into the dating pool.

She pressed the doorbell, listening to the sound of it echo into the house as she hastily tried to straighten out her rumbled dress and tuck an unruly strand of hair behind her ear. She was late. Lorelai's Jeep was already in the driveway and Lorelai hated getting to dinner before her. The woman couldn't tolerate thirty seconds alone with her own parents. Add in the fact that Rory had stayed in Norwalk last weekend and she knew she was in for a rather melodramatic diatribe from her mother when they got back to Stars Hollow later.

The door swung open and her grandmother appeared. "Rory, you're here. Good, come in."

"Sorry I'm late, Grandma," she apologized. "I had a deadline on this article about the city council meeting on this new low cost housing project and I got some really good interviews from the residents who attended but then there was this one quote I wanted to use and I couldn't find it anywhere in my notes and I was going crazy because I knew it had to be there somewhere and…"

"Oh, that's alright dear. Work comes first," Emily replied, cutting Rory off mid-ramble as she guided her into the sitting room. Her grandmother was distracted, her voice distant. Rory was distracted too as her eyes swept around the house. More of her grandparent's normal furniture had been replaced.

"Did you redecorate, Grandma?" she asked. She knew her grandmother loved to redecorate but given the state of their finances, it seemed like a strange time to do it. Unless of course things with Floyd Styles were finally settled and the business was back in business. Rory felt a jolt of relief and excitement at the thought. They must be through the worst. Things were going to go back to normal. Friday Night Dinners were going back to normal.

See? She knew she'd made the right decision saying 'no' to Logan. Not that there had ever been any possibility of saying yes. It was ludicrous to even think she'd marry someone she barely knew for money. Even if Lane was having a field day teasing her about it. She was pretty sure she was never going to live down the fact that her boss showed up at her rinky-dink apartment with a ten-thousand-dollar diamond engagement ring to ask for her hand in marriage. To be fair, it was a pretty funny story. And one she couldn't even tell anyone else. So, joking about it with Lane wasn't the worst thing in the world.

"Do you want something to drink?" Emily asked, ignoring Rory's questions. That was odd, her grandmother usually loved to show off whatever new things she had bought. Why was she changing the subject?

"Umm sure, I'll…"

"Richard, Rory's here. Get her a glass of club soda."

"Of course, Dear."

Rory's eyes narrowed in suspicion. Enough suspicion to start questioning if the new furniture was really the good news she was hoping for. While Rory did go booze free more often than not at her grandparent's, they usually at least offered her an alcoholic beverage. At least ever since she'd turned 21 they had. Rory turned to her mother who brandished the tumbler glass she held with a flourish, somehow avoiding any spillage. It was filled with ice and clear, carbonated liquid. Since when was this a dry household? If she thought her mother was going to be pissed about her being late before, she was going to be doubly pissed about her being late when there was no alcohol available to numb the pain of having to actually interact with her parents.

"Umm, thanks, Grandpa," Rory replied as she sat down on the settee next to her mother and waited for her drink.

Emily sat in an unfamiliar armchair in front of the fireplace. On closer inspection, Rory noted how bland it was compared to her grandmother's usual tastes. Just a plain off-white fabric on a cherry-stained wood. Rory didn't know much about appraising furniture, despite the fact that she had spent many an afternoon growing up in Lane's mother's antiques shop, but she got the distinct impression that the current chair was far less pricey than the old one despite its perfectly nice aesthetic appeal. In fact, as she looked around it seemed like all the new furniture was of a slightly lower caliber than their predecessors.

Richard handed Rory her glass and cleared his throat uncomfortably.

"Girls, your grandfather and I have something to discuss with you."

"Something to discuss that requires we remain completely sober?" Lorelai clarified sarcastically, "You know, lest we get black out drunk from a single ounce of gin and forget the life altering news you are about to share with us?"

"There will be wine at dinner," Emily retorted with an eye roll. "Must you always be so dramatic?" she sighed.

"I'm being dramatic?!" Lorelai asked with incredulity. "You're the ones who have mysteriously withheld drinks at the portion of the evening specifically assigned for drinks, have spent the last twenty minutes whispering to each other in hushed tones, and have answered every question I've had with 'just wait until Rory gets here.'"

"Well, what we have to say pertains to both of you," Richard explained. "There was no reason to go through it twice."

Rory felt a pit form in the center of her stomach. She tried to take a sip of her club soda to soothe the churning sensation but it could barely make it down through the tightness in her chest. This was bad. It was very bad news, she was sure of it. Despite all of her wishful thinking and false hopes, despite every assurance she'd given herself that her grandparents would be okay and her grandpa would be able to fix whatever money problems they were having, it seemed she was wrong. The only question was, just how bad was it?

"Well?" Lorelai asked as Rory struggled to breathe through the burgeoning panic attack.

"Your father and I have decided to sell the house."

Oh god. She knew it was a possibility. Jason had told her mother they'd taken out a second mortgage on the place to get an infusion of cash into the business, but she'd never truly believed it would come to this. She never really believed they would lose the house. This was the house where her mother had grown up. It was the house where she herself had lived the first year of her life. It was where she had spent almost every single Friday night since she was sixteen. This house felt as much a part of her as her own house did. And where would her grandparents go now?

"You've decided to sell the house?" Rory repeated disbelievingly. The words didn't even sound like hers. She was amazed she could talk at all.

"Yes," Emily nodded. "We thought it would be nice to downsize."

Lorelai let out a scoff, chocking on her club soda. "Downsize?" she asked incredulously once the coughing had subsided. "Do the two of you even know what that word means?" Lorelai's parents had never downsized anything in their entire lives. Downsizing was not a thing in their world. It was always about upsizing. It was about the biggest and best next thing. Forget about keeping up with the Joneses; the Joneses were trash who tried to keep up with them.

"It's just that we're not getting any younger and the two of us don't need all this space. And all the stairs aren't good on your grandfather's knees…"

"My knees are just fine, Emily," Richard insisted.

"You know the doctor said you have bad knees."

"It's a little arthritis. I'm not an invalid incapable of taking a set of stairs."

"Either way," Emily said, flicking her hand dismissively. "The house is more than we need. And it's so much upkeep."

"Are you personally cleaning the baseboards and pruning the bushes these days, Mom?"

"Managing a household like this is not easy, work, Lorelai." Emily snapped. "I have to direct the staff, make sure they're doing what they're supposed to, delegate tasks, make grocery lists and menus for the week…"

"Oh please, just admit that you've having money problems and that's why you're selling the house."

"We can take care of our own finances, Lorelai," Richard piped in again. "It's none of your business why we've decided to sell the house."

"But where will you go?" Rory squeaked out, her heart beating fast.

"We've looking at some lovely townhomes in a wonderful gated community in Bristol. We'll be even closer to the two of you."

"Swell," Lorelai mumbled.

"A townhouse?" Rory asked. She could hardly see her grandparents in any kind of living situation that involved shared walls.

"Yes. The homes are beautiful and the community has some wonderful amenities…a pool, a club house, they host a weekly poker night for your grandfather."

"Wait, wait, wait…" Lorelai said, holding out her hand and nearly spitting out her club soda. "Is this a…retirement community?" The words 'retirement community' rolled out of Lorelai's mouth with an amount of disgust usually reserved for rants about Justin Bieber and decaf coffee.

"It's a community geared towards other members of the fifty-five and over community."

"It's a retirement community," Lorelai insisted.

"It's a perfectly lovely place."

"You are going to hate it."

"Well, we don't always get what we want, Lorelai," Richard snapped. "Sometimes sacrifices need to be made."

Lorelai shrunk back into her seat at her father's outburst. The room seemed to go a little blurry, the air around Rory trembling with a distant buzz as her grandparents kept talking, bits and pieces breaking through the din around her. 'Two-bedroom,' 'One-year lease,' 'moving company…'

This couldn't be happening. Her grandparents couldn't live in a two-bedroom townhouse in a senior living community. They'd kill their neighbors. Or they'd be killed by their neighbors. Or they'd have simultaneous strokes from the combination of stress and shame. Anyway she looked at it, someone was winding up dead.

She didn't want her grandparents dead. Or in jail. She didn't want them to lose the home they'd lived in for their entire married life. And this home was important to her too. She had so many memories of her own in his house. And suddenly, through the panic, an unbeckoned thought. She had the power to fix this. She could save her grandparents. But at what cost to herself?

She'd driven back to Stars Hollow in silence. No music, no podcasts, no audiobooks. Just her and her thoughts. What was she going to do? Was the offer even still on the table? It had been a week and a half since Logan had made his proposition. And she knew he was in a time crunch. He'd surely compiled a list of back-ups in case she'd said no, which he had to have known she would. Had one of them said yes since he'd walked out of her apartment that night vowing not to bother her again? He'd been to the Gazette for meetings only twice since then—it appeared he was transitioning back to the Manhattan offices. And he'd barely even acknowledged her but for a polite "Good morning, Miss Gilmore." He was holding to his promise to accept her answer and pretend like nothing had ever happened. Which she appreciated, but it also meant she had no clue about where he was at in his wife finding mission.

And even if the option was still on the table, could she go through with it? Was her grandparents' home and livelihood worth two years of her life? Sure, her grandparents would hate their living situation, but they weren't going to be homeless; they'd survive. On the other hand, it wasn't like it was a prison sentence for her if she took the deal. She'd be living in a mansion and socializing with journalistic royalty. She'd have a dream life…on paper. But she knew enough about the world of the wealthy to know that a perfect life on paper was usually a miserable life full of petty squabbles, backstabbing, and loneliness in real life. A gilded cage was still a cage. But then, in two years she'd be set free with a whole new world of opportunity in front of her. And her family taken care of. Or would they be? That was the other question. Was there enough time to make this work? Logan couldn't put the business investment through and make the necessary steps to secure Grandpa's company before the house was sold.

She pulled her car into her mother's driveway, noting that she'd arrived first. She got out and let herself into the house. It was a mess, which was hardly unusual for Lorelai Gilmore. That was alright by Rory, it gave her something to do to distract her while she waited for her mother's arrival. She started gathering up the magazines her mother refused to stop subscribing to even though you could get everything online now. "But I want to see how long it takes them to figure out there is no Tookie Clothespin," her mother had once wailed dramatically when Rory had called her out on the obscene waste of glossy, unrecyclable paper which was sent to her under multiple names every month just because Lorelai had gotten bored one day and given fake names to telemarketers to see who was selling her info.

She was folding a throw blanket and placing it over the back of the comfy chair as Lorelai pulled into the driveway. She made her way into the house and collapsed onto the sofa in the living room. "I called Jason," she informed her daughter.

"And?" Rory asked.

"A big client pulled out—went back to Henning-Styles. They're trying to figure something out to stay afloat, but it's not looking good. And he said Dad has been having more and more trouble pulling together his share of the legal fees the past couple of weeks."

"Oh my god." Rory started pacing around the living room.

Lorelai sat up at attention, meeting her daughter's eye for the next part. "Dad's got no retirement, no pension. He's spent it all. They've got to be flat broke. And while Dad hasn't said anything specifically to Jason, from what he knows of the market right now and the outstanding mortgage on the house, he's pretty sure they're going to need to file for a short sale."

"But then there won't be any profits left over. How will they even afford a townhouse?" Lorelai shrugged. "And what about all that new furniture. It wasn't as nice as the old furniture but it was way more than they can fit in a townhouse."

"If I had to wager a guess, it's rented."

"Rented?" Rory asked aghast. She couldn't imagine her grandparents sitting on rented furniture that had been used by god only knew who. Which was non-sensical, she knew because most of her grandparent's original furniture was antique, and therefore had been used by only god knew who.

"To stage the house for the sale," Lorelai clarified

"Oh god. I can't believe this is happening. It feels like it was barely yesterday they were making us put post-it notes on everything we wanted them to leave us in the will and now there's not even gonna be so much as an end table left to put in the will."

"Yeah, and I put a post-it on the house!" Lorelai added indignantly. "That's my house they're selling."

"This isn't funny!" Rory insisted, stopping her pacing and throwing her hands up in exasperation. How could her mother joke at a time like this? "Don't you care at all what's happening to them?"

"I care that they're going to be barely 20 minutes away in Bristol."

"Mom!" Rory protested.

"Oh Kid, come on. You know I care. But what am I supposed to do about it? Pull 15 mil out of my back pocket and buy the house myself?" That was it! She could buy the house herself. Or, well Logan would have to, she supposed. But it would need to be quick. Before anyone else could get an offer in. Which meant it would need to happen before the wedding. Would Logan even be willing to do that? Buy her a house before she fulfilled her end of the bargain? "What?" Lorelai looked at her daughter with suspicion.

"What 'what?'?" Rory asked.

"You've got that look on your face."

"What look?" She averted her gaze instinctually.

"That look like you're Eddie Redmayne in The Theory of Everything and you've just realized how to integrate gravity into the standard model."

"Hawkin never solved the theory of everything. In fact, he eventually came to conclude that such a theory would forever remain out of the grasp of human knowledge."

"Okay ivy league diva," Lorelai huffed. "The point is, there's something going on in that little head of yours, I can tell."

Rory sighed, taking a seat on the couch next to her mother. "I just…what if I told you I might have a way to help Grandpa and Grandpa?"

"I'd say where have you been hiding that eight-figure trust fund? Did your paternal Grandparents suddenly decide to make up for 27 years of neglect with a big cash payout?"

"I don't have any secret money," Rory rolled her eyes.

"So what? This is some organized crime deal? Because I'm too pretty to go to jail for money laundering. And I don't care how cute George Clooney is, I'm not pulling an Ocean's Eleven casino heist. Those places are run by the mob and you do not want to be on their bad side."

Rory let out a giggle, feeling a moment of relief from the all-consuming panic that had been clinging to her every cell all night. Her and Lorelai had made the same joke—that had to be a sign right? Not that they never made the same joke before, but not like this.

"Hey! Don't make fun of your Momma," Lorelai protested. I brought you into this world and I can take you right back out again."

"No, it's just…" Rory gasped, trying to get a hold of her laughing. Once her breathing had finally normalized, she continued. "Let's just say if I go ahead with this thing, I'll be the one winding up with 'George Clooney'!" Rory empahasized the name with finger quotes.

"Nuh uh!" Lorelai protested. "Clooney is mine. You can have Brad Pitt. Also, you still haven't explained your plan. Because, I have to tell you, if the plan is to seduce one of People's past Sexiest Men Alive into giving you the money to bail your grandparents out, I will cede Clooney to you in exchange for Idris Elba.

"There will be no seducing," Rory insisted with an eye roll. "And no past Sexiest Men Alive will be involved." Although she was pretty sure she remembered Logan winding up on one of Business Insider's lists of Most Eligible Business Bachelors. God, what was she contemplating getting herself into.

"But there is a plan? I mean, you said there was, right?" Lorelai asked, getting serious again. "Because honestly, Honey, I'm struggling to come up with any plan where you could come up with eight figures that doesn't involve illegal activity. And you freak out when you don't return a library book on time. I don't want you getting into anything dangerous here. Your grandparents are grown-ups, they can figure things out for themselves."

"It's not dangerous." She didn't think. She didn't know Logan very well personally, but there was more than enough public information available on him to feel confident he wasn't an axe murderer. Plus, he was on the Yale Daily News with Paris, and a few people she knew from Chilton ran in the same circles as him. She could get some basic information about the kind of guy he was. Though she might want to take Paris' advise with a grain of salt; the girl hated literally everyone. Plus, she felt quite certain that Logan would insist on putting every single contingency in the pre-nup so the money aspect and expectations would be clearly spelled out in legal documentation. She'd be protected. Of course, that was if she even decided to do this, and that was a pretty damn big 'if.' There was once hell of a pro-con list in her future before she made any life altering decisions. This pro-con list would put the Harvard-Yale-Princeton list to shame. "And it's not really a plan. Not my plan anyway. Just a…friend willing to help me out in exchange for me helping him out."

"Can you stop with the cryptic already? You're freaking me out here, Kid. What kind of friend do you have that can solve this kind of problem? And what could you possibly be helping him out with to make it worth it. This isn't some kind of Indecent Proposal situation is it? Because it didn't turn out well for Demi Moore and it won't turn out well for you."

"I mean, it didn't suck for Demi Moore," Rory shrugged. "Woody Harrelson's character kind of got the short end of the stick for a bit there. But Demi got to have a hot, steamy affair with Robert Redford and still in the end wind up back with her true love. And I don't even have a Woody, so…"

"But you have a Robert?"

"Not exactly."

"Oh god." Lorelai buried her head in her hands in frustration and fear. What was her daughter getting herself into? Why did she always feel like it was her responsibility to solve everyone else's problems. She still had no idea what this brilliant plan was, but it sounded dangerous. And more than a little creepy. No one just gave away millions of dollars to a pretty, twenty something girl without major strings attacked. This was bad. Very, very bad.

"Look, I haven't even made any decisions yet. I don't even know if the offer is still on the table. And I want to tell you, I do, but I can't. I said I won't say anything. But if I decided to take the offer, I promise I will let you know exactly what's going on.

"Rory, no." Lorelai insisted, her feeble attempt and putting her foot down when it came to her fully grown, overly independent daughter. "I don't know where the hell you're going with this, but I don't like it. Your grandparents are grown-ups. They can be responsible for their own lives."

"They've helped me" Rory insisted. "They paid for Chilton, for Princeton. They bought me my car. I wouldn't be even close to where I am right now without them. I owe it to them to at least consider this. We're family, we help each other out. It's what we do."

"Rory…"

"Don't worry, I promise, whatever I choose, I'll be okay." She would. She'd make the choice that she could best live with. It would take sacrifice and compromise no matter what option she picked. But she meant what she said…she owed her grandparents so much. And if she could do something to help them, she owed them at least the consideration of doing so. So this was it, she was really considering marrying her billionaire boss.