'Every ride has to end,' Rory had kept saying that sentence to herself ever since she'd left the King's Head Inn in New Hampshire on that heartbreaking October morning. She knew too well that while her connection to Logan had been magnetic, neither of them really fit into each-other's lives anymore, and neither of them was willing to alter their lives permanently to change that. She couldn't picture herself in the role of the typical eye-candy who just stood by Logan Hunzberger, marketing CEO of the HPG, attending cocktail parties and red carpet events, while spending most of her alone while her husband spent a significant amount of time abroad or at work, and was constantly surrounded by adoring hordes of beautiful women. At the same time Logan would never have been fully content settling for a life in some mediocre small town in Connecticut, where job prospects for someone of his status were non-existent. He was exceptional at what he did, and similarly to his father whether he liked to admit it or not, success was what made him feel alive. Plus there was the matter of his impending marriage to a perfectly lovely and intelligent woman. Their ride had ended, and it was the right thing to do. They both knew it.
Rory didn't have time to wallow, even though thinking back to that night made her heart wrench. Thankfully, she had a book to write, a welcome distraction, and the first chapters just flew off her keyboard within a few weeks sitting at Richard's old desk in Hartford. She had hardly left the place in two weeks, having food and necessities delivered. The place was huge and even keeping the couple of rooms she used tidy during those days was a lot of work. She'd never thought about the maintenance part of Grandma's and Grandpa's place as they always had a fleet of servants handling those things, but here she was now, all alone. She hadn't left things perhaps the best way with Lorelai, who wasn't in full agreement whether she should indeed write the book she needed to write. But she was determined to change her mind. At the very least she herself just needed to let the story flow through her. The process itself was therapeutic. She'd told herself that if Lorelai said 'no' the second time, after reading it, she would just need to accept it.
It was Friday, and the delivery lines at 8 PM were surprisingly long for that area of Hartford that night. she pulled on some simple jeans and a clean t-shirt before grabbing her keys and headed off. While she'd gone to school in Hartford, she never really hung out there much. This also meant she needed to browse a bit before deciding on a place to eat. Between a row of coffee-shops, a few bakeries, a vegan restaurant and what appeared to be a couple of fine dining establishments she noticed a bar with menu specials written on chalkboard outside. The thought of simple burger and fries was all she needed. While she ate, she felt the change of scenery refreshing and while the bar scene was not truly her thing she found it surprisingly interesting to people-watch while half-seriously browsing her phone. A middle-aged couple at the bar were having an argument over some tequila shots, an interesting way to solve problems, she thought. At the back of the bar group of college students, with Uhart sweatshirts, were celebrating something with jugs of beer. The group had an interesting group dynamic where all the girls seemed to be wailing over the two guys sitting in the back of the booth. She'd seen that dynamic often in Yale, when Logan and his Life-and-Death Brigade friends hung out. All of them wealthy, bound for success and handsome. They pretty much had to drive girls away. Her eyes moved back along the bar only then noticing a lanky hunched figure, slowly sipping his scotch, alone. She almost didn't recognize him. The times she'd seen him in the past years, which was of course less than in their Yale days, he's seemed lively, confident and witty even though almost always under the influence. But sitting at that barstool, Finn looked incredibly sad. Rory grabbed her small beer glass, still half full, and walked over. While he was one of Logan's best friends, and they'd never before hung out just the two of them, she, too, considered him her friend through him.
"Finn, is that you?" Rory asked carefully. His face looked tired, a bit rough and unshaved, small wrinkles showing around his eyes, and his medium-length hair was uncombed.
"Hey, gorgeous! Wouldn't have expected to see you here!" he greeted, but uncharacteristically to him in a low and dull voice. He didn't think he was ever going to see Rory again once she and Logan had left their separate ways since New Hampshire.
"Are you okay there, Finn?" Rory inquired carefully. He didn't sound like himself.
"Ah, just... not having the best day," he dismissed, and took a sip.
"If you want to be alone, I can leave…," Rory suggested hesitantly.
"You don't need to, not on my account. I just may not be the best company at this point," Finn explained.
"If you want to talk about it, I have nowhere better I need to be tonight," she offered.
"I guess the very gist is that I am having a mid-life crisis of some sort," he explained.
"Well I am the expert on the issues of the 30-somethings," she said jokingly. She'd recently moved back home, had hardly any paying gigs and nothing she had thought she would have achieved by the age of 32, had materialized. If it wasn't for her book, she'd be in his position, except probably drinking home alone to save some money.
"How's life treating you?" He changed the subject slightly.
"I am either at the very bottom of my own mid-life crisis or just a tiny bit beginning to rise from it," she described, squinting her eyes at the last part, hopefully.
"Shall we drink to that, then?" he offered, and they clinked their half-empty glasses together.
"I am writing a book," she decided to share, "I am not sure if it'll ever get published or anything, but I just felt I needed to write the story," Rory added, "it's basically about how I grew up with my mother, she raised me on my own. But other than the book, there is little going on in my life right now."
"That's pretty cool, I never was much of a writer," he sighed. "My main problem is that I've grown tired of the life I've lived for the past decade and some odd years. And I feel I need to figure out who I want to be and how to make that happen."
"I guess I can understand that, your friends, the ones I know of at least, are settling down," she said thinking about Logan and Colin, "and the partying can get a little old."
"Exactly," he said, "now you see, I am not very original."
"Do you live in Hartford? I thought you were in Boston," she asked, shifting the topic.
"Ah, yes, I have a place in Boston as well, but I recently transferred to Hartford for the family business. Here to stay for the foreseeable future." he replied.
"Shall we drink that?" she suggested, "to new beginnings!" as they gulped down their respective drinks. Drinking with Finn had always come the easiest. Life and Death Brigade events were never dry but then again here he was saying he'd had enough of that side.
"Weren't you living in Stars Hollow?" he inquired.
"I was, but for now I moved into my Grandparen't place, they aren't using it anymore, and it's close by here," she explained, "If I can find a job in Hartford, I might stay."
"So you are looking for writing positions?" he not so much asked, but stated.
"Yes, any type of writing - copywriting, editing, reporting...willing to explore all options," she replied.
"I'll keep my eyes open for you," he offered.
"Thank you, that's sweet," she smiled, trying to remember the last time, if ever, she'd had a deep and serious conversation with Finn.
"I'll just see if I still have your number," said checking his phone. "Ah yes, there we have it," he said and pressed "call". Rory's phone rang once leaving Finn's number.
"And Finn, I am confident, you will find yourself again, maybe not again… but the new your," she said hopefully, preparing to leave.
"It was great seeing you," Finn said and hugged Rory goodbye.
"You too, hang in there. The only way out of a rut is up, you know," Rory whispered.
A week later Rory was doing laundry at the Hartford house while her phone rang, an unknown number.
"Rory Gilmore speaking," she answered officially hoping it would be one of the places she'd sent her resume to.
"Hi Rory, it's Finn," he said. She'd forgotten to save his number.
"Hi! Good to hear from you," she greeted.
"Listen, I checked around a bit at our company, and I don't know how you would feel about the field, but there is an opening for a copywriter at our company. I know it's maybe not right up your ally, but if you want, I can get you shortlisted. It's part time, about 30 hours a week, benefits included." he described.
"Thank you for the offer. I don't have anything else lined up just now, so I'd definitely apply," Rory said. While she did have a trust fund and possibilities to ask support from her family, she didn't want to touch those options for everyday expenses. Even though this job was quite far from her dream job as a travelling journalist, she felt it was time to just try to push through this period of life and do something.
"I'll send you the info," Finn added.
"Thank you!" she replied before hanging up.
She walked into the building of Morgan & Stewart downtown Hartford wearing a navy knee length pencil skirt and a blazer, looking confident. She took the elevator to the third floor and let the administrator know she was there. She was perfectly on time, two minutes early in fact.
"It'll be just a minute," the red-haired receptionist said, gesturing for her to take a seat.
The place was sleek and minimalistic, decorated in light colors.
"Lorelai Gilmore?" the receptionist spoke again, "Mr. Johnsson is ready for you in room 12 to your left."
Fifteen minutes later Rory walked out of the meeting with a job. While she had never worked as a copywriter before, she knew that writing anything wasn't going to be an issue. Her resume was good after all, just a little patchy. Besides there was a whole marketing team there for support, and she would just be one of the writers. She knew she would be able to pick up anything she lacked on the go.
As she got outside, she went through her purse in search of her phone and dialed Finn.
"Hey Rory! What's up?" he replied.
"Hi Finn! I just got off the interview. Thank you, Finn! That must've been some short list." she said.
"No problem. You are probably way better than what we need anyways, but I am glad I could help."
"Listen, I really would like to take you out to dinner or something, to thank you in person," she offered.
"Sure, I have no objections with that idea. It's not like I know many people here besides the office crowd."
"Does tomorrow evening work for you?" she inquired.
"Sure," he replied.
"I'll text you time and place," she suggested, "See you then!"
"So just tell me, how directly are you going to be my boss?" Rory inquired after the official 'how are you's' they'd exchanged after taking their table at Luca's Italian restaurant, having just ordered their food.
"Well my opinions matter as I am one of the owners, but I am in a different department really. You'll be in Marketing and I'll be at the Legal department," he explained.
"Good, I wouldn't want it to be weird," Rory said. She'd seen plenty of Finn's hilarious drunk side in the past and she wasn't sure she could keep an entirely straight face when she half expected him to start sweet-talking the inanimate objects, when working under him.
"It's a fairly small town, people know each other from various places, I doubt it'll be an issue." he added brushing it off.
"How's the rut?" she asked a bit bluntly, just as their food was brought to the table.
"It's still in the back of my mind I guess, but I've figured that now is a good time as anytime to make some changes - being here in Hartford instead of Boston, where it is just too simple to fall back into the same scenario, can only help," he explained rubbing his forehead.
"I am glad to hear that," Rory exclaimed, biting on her ravioli.
"You may not know this about me, but my family is quite the atypical version of high society. Yes, they too work hard but we're a close knit bunch. We celebrate holidays together, we go on trips to Australia to visit my grandparents and there's always a bunch of kids around," he described, adding, "And I really think the next step is to really try to push my life in that direction."
"Settle down and have kids?" Roy asked surprisedly, with lifting her eyebrows.
"Sure, if I find the right girl," he replied somewhat doubtfully, and took a sip of wine.
"That is very different from the Finn I've know until now," Rory commented "But I can't say that it is an unwelcome change," she added with a smile.
"I don't feel I've completely wasted my time until now, I love a good party, but I do feel I don't have that much time to waste left. I don't want to be some 50 year old with a gold-digger twenty-something at my side just for my money, just so I can have some kids," he continued.
"Well I guess it means you really are embracing the different side of in omnia paratus," she concluded.
"I guess, that is one way to take it," he replied, giving a small side-ways smile.
After a lengthy overview of the inner workings of Morgan & Stewart by Finn, a glimpse into Rory's overview of the crazy world of Stars Hollow and dessert, Finn suddenly got quiet.
"Listen, Rory, I know it might sound a bit unexpected to you and maybe it's just too weird, taken our joint friend in London... Feel free to tell me if it is. But how would you feel about going on a date with me? I mean, today, sure, it's not that far from it, but like officially," Finn asked.
Rory's mouth fell open slightly. "I don't know what to say...," she began, still thinking what and how she should reply.
"I'm sorry if I was out of line, you are a great friend. The answer won't affect your work opportunities in any way if that's what you are worried about. I just thought maybe…" he added hesitantly.
"I have thought of you like a friend, but I don't really have any objection to the idea, it's just unusual for me to think of it like that," she with a sigh, "And I just don't know if it would be fair to you just yet, I don't want to use you, like to rebound or something."
"Are you still hung up on him?" he asked straightforwardly.
"There are still residues of him, sure, but I know that it is over and done with and I am not hoping things were different - our lives just are and will be very different always. It had just dragged on for too long and I am not proud of those circumstances. I am determined to move forward," she explained.
"You don't have to worry about hurting me or whatever, I am still new at this 'dating for real' game. It's like a practice round for me, too. I am not even sure if I know how to do that. Getting women to come home with me or spend time with me when I am buying drinks for them has never been an issue. The part of actually getting to know them is new. And with you I feel there is somewhat less pressure - I know of you at least, I know you are smart, funny and I enjoy talking to you, not to mention you are beautiful," he said, unsure if he was crossing any boundaries at the end of that sentence.
Rory blushed a little. "Thank you for saying that. Alright, Finn Morgan, I will go on a date with you." Rory stated, still unused to this idea. Finn had always been sort of Logan's, putting it poorly, side kick. It was as if she never really saw Finn - she'd seen him running around naked, sure, but other than his witty banter and adorable Australian accent, she didn't really know him. But with his new change in attitude towards life, not to mention, that he hadn't drank more than a glass of wine the entire evening and the fact that he was quite handsome and interesting to talk to, she had little against the idea of trying. The only ponder she had, was how would Logan take it. But at this point, there was nothing he would ever have to know.