Chapter 4

September 12th, 2021

Rory was just pulling up to Maple street, still having a couple of hours to kill before she was due to pick up Em from Jess'. She might have gone to Lane's like on some weekends, but it was Zach's birthday party and as Lane had put it - the place was full of all kinds of hairy and smelly guys - from which she'd suggested Rory better stay clear of.

Hence Rory made her way to her mother's, seeing already the living room light on from the driveway.

With an energetic step she made her way up to the porch and entered.

"Hey," Rory called out.

But she couldn't see a soul, continuing from the livingroom towards the kitchen.

Then there was definitely some rumble coming from upstairs. Rory could only guess it was either Lorelai cleaning her closet, feeling particularily frustrated about her mismatching shoes, which rarely happened, or...maybe she'd interrupted something. The sound certainly was a lot like Lorelai getting dressed hastily - she'd grown up with that sound.

Rory hesitated for a moment - should she really have called first?

Lorelai made her way downstairs hurriedly, dressed in pajama pants and a robe, clearly looking a little flushed.

"Hey," Lorelai greeted her daughter who was already in the kitchen, getting her old mug out of the cupboard. Obviously she was pretening that nothing was out of the ordinary.

"Sorry," Rory whispered in a low chuckle, knowing that the one who was truly embarrassed would be Luke, who was probably going to insist on not showing his face before she left. And like on cue she could hear the low mumble of a football match, Luke having turned on the upstrair TV.

Lorelai simply mused at her words, not letting herself be bothered by this. Rory was always welcome, and it was not like Luke was going anywhere.

Without asking, Lorelai poured Rory a cup of coffee from a semi-fresh batch and placed it on the table in front of Rory with a pack of chocolate espresso cookies.

"How did yesterday go?" Lorelai asked. She'd seen both of her girls, Rory and Em, for Friday night dinner, but they were still pretty close, at least talking a couple of times a week, less so during the working week though.

"I'm getting my glasses next week, yay!" Rory said, with an unenthusiastic exclamation. "Nice glasses, but I'm not sure they do me a lot of favors," Rory added as an explanation.

"Eva Mendez, Christina Hendricks, Gisel Bündchen… all prime role models as glass wearers," Lorelai began her encouragement. "Now you just need to you know… do something about that wardrobe of yours," she critiqued, nodding in her direction.

"What's wrong with my outfit? It's my day off!" Rory objected, looking down at her leggings and slouchy cardigan combo with a simple t-shirt underneath. Her outfits for work followed a worked-in pattern of slacks or knee-length pencil skirts, blouses and blazers or sweaters. She looked sophisticated, smart - sexy being a side-effect on occasion rather than the goal in a classroom filled of hormonal teenagers. Her outfits were more relaxed than what she'd worn to some former engagements in the corporate world. But it was true that her job allowed her less chance to experiment with flattering dresses.

"Let me just ask, when was the last time you had dinner with a man - and Luke doesn't count," Lorelai shot back, rolling her eyes.

"I had lunch with Finn yesterday, surely that counts for something, he's a man...," Rory shrugged, not liking where this was going. Rory knew she was lonely, but she didn't need her mother to rub salt in her wound.

"Finn? Really?" Lorelai asked both in disbelief and curiosity, squinching her eyes. Sure, Lorelai knew Finn dropped by to catch up every once in a while, but frankly she was desperate for her daughter to find some happiness in her life. She knew what it was like to be a single mom, and while she didn't want Rory to rush bringing a man into Em's life, there was a lot a couple of good dates did for a woman. She just didn't want to resort to her own mother's ways by beginning to set Rory up, though she'd been tempted a number of times by now.

"We're friends, mom," Rory chimed.

"But he's been dropping by quite a lot, hasn't he?" Lorelai discussed, recalling Rory mentioning him at least a handful of times during the past half a year.

"He visits his sister, she lives close by. Hartford is on his way. I guess he's just had more reason to go there over the summer," Rory argued.

"Are you sure that's all there is?" Lorelai found herself saying. As for the couple of times she'd met Finn the man hadn't exactly appealed to her, especially from her experience with him hitting on her at Bridgeport police department. But she too believed that the man wasn't an exact copy of the spoiled playboy he'd been back in college.

"Yes, I'm sure," Rory replied sternly, shaking her head. Surely, that was all that it was, right?

"I just mean it's an awful lot of dedication on his part to catch up with old friends with such frequency, either he is a very good friend or…," Lorelai hinted.

"It's nothing like that," Rory argued. It seemed unlikely, and Finn was hardly known as the guy who was unclear about his intentions with the ladies.

"If you say so," Lorelai shrugged, secretly happy to have at least planted a tiny seed of thought into her daughter's brain. She was sure she had. She didn't even need to see anything happen between them, but it was that same line of thinking she wanted her daughter to have - to play that game of who likes whom, flirting, hinting. She wanted Rory to grab control over her life - ask someone out, look for happiness for herself too, not just for Em.

Rory was quiet, taking a sip of her coffee. She was on the verge of admitting to her mother that she'd instead had a lapse with Jess a few weeks ago, but she was just too embarrassed. She didn't want her opinion on those matters - not with Jess. Jess was practically family as he was and she knew that in this househould Jess would always have supporters.

"So did you think of a performer for the upcoming wedding already?" Rory asked, changing the subject so something Lorelai had mentioned on Friday about an event that was booked for the Dragonfly a few months from now.

A few hours later, Rory drove her car through Stars Hollow, waving to a few of her closer friends as she did. The place was still home, but there was definitely a small fraction of the town that had also taken a liking to Jess, some even choosing sides after they'd split up and Jess had permanently moved back to Stars Hollow. He'd first lived above the diner, while he was still fixing up his store and the floor above for him to live in. Andrew had closed his store and moved to Boston, hence Jess' bookstore really was welcomed in this small town - it was him who'd stayed and contributed to the community, unlike Rory, whom some considered thought she was too good for Stars Hollow these days. But Rory, being busy as she was, most of the time, hadn't really had time to ponder about her local popularity. Either way - she had nothing against Em receiving some of that community feeling she'd had growing up in this place.

It was a Sunday, so the bookstore was closed. Rory parked in front of the red brick building and made her way through the small pedestrian gate at the side of the building that took her to the back entrance. The place really had Jess written all over it - slightly industrial but still homy, even having a small patch of outdoor space where Emma could play, her swing and slide set being a prime example of that.

Rory knocked on the kitchen door window in the back, and waited. She had a key, but she was making sure to keep her distnance.

"That must be you mom," she heard Jess' deep voice say, as he made his way towards the door. The patter of steps coming down the stairs behind him were self explanatory already.

"Hey," Jess said as he saw her at the doorstep.

"Hey!" Rory exclaimed, putting up a cheery face, trying to ignore any lingering awkwardness, including Jess' gaze. "You ready to go?" she quickly turned her attention from Jess to Em who'd reached the door by then.

Em simply clung to her mommy, hugging her, making Rory's heart melt.

"Did you finish packing?" Jess asked Em.

"Yeah?" she replied, not sounding too sure in her response.

"Well, why don't you go check and bring your backpack downstairs," Jess suggested, his eyes still studying Rory.

Rory could tell - he wanted a word in private. That was what she was afraid of.

Em made her way back upstairs, Rory almost beginning to caution her to be careful on the stairs much like she would at home, but Jess beat her to it, making her smile a little. There was no doubt that they both loved that little girl.

"Listen, I was wondering if you had any plans for next Saturday night," Jess asked, as he leaned against the doorway, knowing that Rory rarely was eager to come inside. In the context of what he was asking, he was being cautious not even bringing up half the things he would've liked.

"Um.. I actually have a date," Rory lied, not knowing where that had come from. She could've said she had to work or had some arrangement with one of her friends, babysitting or anything really… but no - she had to go tell that lie. It seemed to be efficient though, and she could tell as the smugness poured out of Jess' face. Clearly their little encounter two weeks ago had done just what she'd feared - given Jess hope that things might go back to the way they'd been.

"Right," Jess responded. "I would've suggested seeing the 'Power of the Dog' maybe, just as friends, of course..." he added anyways, knowing Rory well enough that she wouldn't have agreed on anything more. He had his suspicions that Rory might be making the date up but he decided to put his suggestion out there anyways. His plan was definitely to ease her into thinking about them again, knowing it was his only chance. "Mom wanted to do some kind of a girls evening with Doula and Em," he added an explanation, as to why he hadn't needed to factor Em in for Saturday night.

"It's nice of you to offer, but I already have plans," Rory shot him down.

"There you are!" Rory exclaimed, seeing her daughter carry her backpack with her.

"Bye, sweetie," Jess crouched to Em's level and gave her a hug in goodbye.

"Bye daddy," Em mumbled to his ear. That sight never got old, not even to Rory.

"Bye," Rory exhaled, waving her hand as she led her daughter towards her car, taking several deep tactical breaths as she walked.

In the car Rory put on the playlist from "Sing" animation, knowing Em loved it, and would often sing along. She just didn't feel up to asking her about her day just yet, the 40 minutes drive providing her with some time to think.

There was no question that for Em, giving Jess another try would've been the best option. But she also knew that it was the most dangerous one, potentially getting Em's hopes up. But the truth was that she just didn't have a lot of belief in the two of them. Sure, the physical had come easily, but the rest - it felt like falling back into their old pattern. And it wasn't like she hadn't tried - she'd tried for nearly two years after Em was born, she'd put her issues up to her struggling with parenthood and being busy all the time, but it had never just felt right. There were things he didn't get.

After they got home and she ordered Em and herself some pizza, which they ate while she asked Em about her weekend, Em snuggled up into the comfortable armchair in the living room that had become mostly hers to read. They both liked their alone time - and Rory retreated to her study desk, the gridded glass door remaining open between her and Em. They were together but in separate worlds in their minds.

She'd done all of her homework for next week last night, and she didn't particularly feel like starting something new. Hence she simply contemplated over her life while staring at her cursor blink at the search field.

Everything was pointing in the direction that she needed to put herself out there again. She should date - shouldn't she? This way she wouldn't have to lie to Jess. This way her mother would get off her back, and maybe, just maybe that craving for the physical and that deep loneliness within her would also subside. It seemed like a simple fix, but she knew it was so only in theory. She really wasn't up to going to bars or worse - bingo nights, or start going to DAR fundraisers or the club, where she still had the Gilmore family membership even.

She typed Bumble into the search field with a deep sigh, and set up an account for herself. But to her surprise there was actually a certain excitement that she felt while doing this - some hope, perhaps? Maybe this really was the right way forward?

Step by step Rory filled in her date filters:

- male;

- age between 30-45 years;

- distance 40 miles;

- verified matches only;

- height at least 5 ft 7''; Her own height at least, or was she just being too picky?

- exercise - couldn't hurt, but no health buff;

- star sign - insignificant;

- education... here she struggled. She wanted someone who could hold an intelligent conversation but Jess was a prime example how the lack of a college education really hadn't played a role. Hence she stuck to high school education, adding a small comment that the person shouldn't be intimidated by women's higher education level. She knew already this was an issue quite often.

- Drinking was okay, in moderation.

- Smoking - preferably not. Rory had tried going out with a smoker once, a few months after Jess had moved out, but it had taken that little to put her off the guy the second she'd kissed him. Yuck. She couldn't even have a one night stand with a smoker.

- Pets were fine;

- Intentions preferably more than just a casual hookup;

- Mentioning children on her profile felt intimate, also demonstrating her major flaw to many potential matches, but she wasn't going to hide it, not a chance. Not when she tried to look for more than something casual. She'd tried that too - but she was a girlfriend kind of girl, and that hadn't really changed. Anything less usually just made her feel like crap. But she certainly didn't mind if the guy had kids of his own though she realized it'd make some things more complicated no doubt. After all, kids usually came with their mothers, i.e. complicated exes.

- The religion filter she left empty - there were too many minor deviations from the mainstream religion branches these days that she really hadn't bothered to keep up. She was open minded and determined not to discriminate based on this, at least not initially. It was the guy that mattered, right?

- Politics - that was another topic altogether, and she really took her time to pinpoint what she believed in, not wanting to really to argue Trump vs Biden at the dinner table. She had a pretty good idea that section alone gave a pretty good impression of her ability to understand the world, her argumentation skills and broad world view. But she didn't want to be defined by just that either.

But then it was time for her to actually write something about herself. She started with picking out a photo of her. There was no point showing her younger self, hence she picked a photo of herself out in the park where they'd had Emma's third birthday, where she was leaning against a tree, wearing a zaffre blue ruffled dress, the late afternoon sun casting its warm light onto her. It was actually Jess' sister who'd taken the photograph - she was pretty good at that for a teenager.

"Single mom, passionate about her teaching job..," she began to write but retracted it, the line sounding like the most boring statement ever.

"Bookworm by soul, hoping my life would involve some more adventure," she wrote, but after a half a minute of thought retracted it. That sounded like she just wanted to get laid, which was the truth of course, but she didn't want to start with that.

"Tacos are the world's best hangover food, coffee is holy water…," she began, but didn't want to be defined just by her consumption habits. They were important, she didn't want someone judging her by her appetite just maybe not that important.

"I've seen the world, I've found home - now just looking to broaden my horizons locally," she typed. But it still didn't feel right.

'"Don't try online dating, it never works" my brain says,' Rory typed, and after pressing save, just for laughs, pulled the lid of her computer down, not having come up with anything better than that. At least she was honest. She knew she'd still need to take on the hard task to read through some other profiles, her initial goal being to arrange herself a date for next Saturday. Maybe later - she thought.

Rory snuggled up on the couch opposite Em, smiling at her briefly. God, how she reminded Rory of herself in her age.

She grabbed the book from the sidetable -"Somebody's daughter" by Ashley C. Ford, that she hadn't started yet, but before she could get into it, her fingers browsed her feed for a minute. Before she knew it she'd typed in Finn Morgan into the search field - and there he was - unfollowed but still befriended. There were numerous pictures of him out and about, some from party settings and some from his day-to-day. He didn't seemed to be involved, not really flaunting arm candy these days. There were a couple of pictures with Robert and Colin but not much else, thankfully.

Finn was a good friend, he cared, he was funny. Could a friendship turn into something more, no matter how unlikely? - she pondered, still feeling a little frustrated by her mother who'd put the thought into her head.