The Simpler Life

6

Chapter 6

"So, how on Earth did you end up in the investigation business? I wouldn't have quite pictured you doing something like that," Rory commented, sipping on her ginger ale, half-way through dinner at Peppercorn's in Hartford. Rory had just listened to Tristian talk about what he did for work. He was an investigator of sorts, not quite a PI as such but something similar, mostly focusing on frauds and corporate espionage cases as far as she'd understood.

The restaurant was definitely on the nicer side and definitely with date-like atmosphere. But there had been no actual mention of this being a date, nor had Tristian done any picking up as such. While he seemed to be enjoying her company, along with occasional flatteries, he didn't look like he was there to make her swoon over him.

Rory had spent a little too much time in front of the mirror that evening before coming here. Not so much because she was aiming to grab at every ex-boyfriend straw she saw and be the cougar this evening like Paris had suggested, but rather to make sure her tiny bump wasn't too prominent. She was finally getting to the stage where the majority of her clothes no longer fit her and every maternity outfit she owned was either too big or making her pregnancy too evident. Rory just didn't want the entire evening to revolve around this one detail even if he did notice. As a result, she didn't really feel like herself in the outfit that she'd come here in - a pair of nice leggings and several bouncy layers at the top – a blouse, a vest and a cardigan. She felt like the outfit gave a message like she was trying too hard – and her boobs were really not helping – but if anything, all that she was really trying was distracting him.

And while essentially, they were just a couple of old friends, catching up, that charming twinkle in Tristan's eyes was still there, and Rory found herself enjoying his honey-toned words, even if it wasn't too serious, Rory smiled probably more than she normally did. She was getting a moment away from her worries after all. Was it flirting that they were doing? She wasn't quite sure of that, at least half of it being very subconscious and based on reminiscing.

"It's kind of a long story," Tristan said, the answer seeming like his standard answer to most questions. Thankfully, this one he did elaborate on a little - "I guess it just came in handy being able to think like a criminal," he added in a chuckle, recalling his own issues with the law, long ago. "But for real, I just had a surprisingly good grasp on the business and law side of things, but I just decided to put that knowledge into good use in a field that offered a little bit more adrenaline than sitting in a courtroom," he explained.

"I can see how you might like that," Rory commented, approvingly. "I bet your dad was over the moon with this path of yours," Rory added, assuming that he wasn't. This seemed to be a running theme in society circles – the parents hardly ever wanted what their kids wanted, but all the kids really wanted was to be accepted as they were. Her mother. Her father. Tristan. Paris. Logan... Rory hated that her mind kept drifting back to him regardless of the beginning of her thought.

"That old bastard is six feet under, thankfully. But I doubt he would've liked it, no," Tristan chuckled, talking about his father.

Rory didn't really know how to comment on that. Sure, she knew they had never been close, but it was still a little harsh to hear that someone was glad a parent had died.

"What about you? What have you been up to? Writing? I thought I noticed some big piece for the New York Times when I was looking you up?" Tristan asked, knowingly.

"God, I hope you didn't go doing some big deep dive into my past without my permission," Rory tried to laugh off her fear, hoping to avoid going into too much detail.

"Don't worry. I 'barely' went deeper than the first page on Google to get your number," Tristan chimed, using air quotes, cheekily.

"No! What did you find!?" Rory exclaimed but kept up a humorous tone.

"Well, I didn't actually get to read the entire thing but there were traces of a blog having existed a while back - keywords being 'Rory Gilmore sex boat'? That's definitely something I've got to hear the story behind...," Tristan challenged her, a smug smile on his lips.

"Well, you know - that's something you'd call a 'long story'," Rory replied, teasingly, but intended to avoid sharing that particular story.

"Ha-ha, you got me there," Tristan laughed. "Are you sure you don't want any wine?" he offered, having already drunk a little more than half a bottle by himself already.

"No, thank you. I'm fine. It makes my head ache these days," Rory fibbed. She wasn't even sure why she was so insistent on hiding her pregnancy – she hardly believed her outfit was good enough to fool anyone.

Tristan poured himself another half a glass.

"So, how have you been otherwise? Anyone significant in your life? Kids? I guess we're getting to that age where we're supposed to start asking about things like that," Rory chuckled, nervously, finding herself a little rusty to be inquiring about these things.

Rory wasn't really sure what kind of an answer she was looking to hear from him. She was trying so hard to stay optimistic throughout the night like this could be a start to something fresh in her life, but she just couldn't shake the feeling how there were little orange, not quite red, flags all over this man. The way he drank, the way he searched for adrenaline or talked about his family. She could've said those same things about Logan in many situations, but somehow from Tristan's mouth they were not as excusable in her eyes. And at least so far, Rory didn't see that fragile, misunderstood, boy, underneath his hard exterior she'd once seen and felt for.

"Never married. But I do have two adorable twin boys in Boston, whom I don't see hardly enough," Tristan replied, and went on to explain the highlights of his own version of complicated. This enabled Rory to relax a little, allowing her to see nobody's life was perfect.

But the reality of a whole other level of complicated hit Rory when she realized how challenging even considering dating anyone would be in her situation. Children from a former relationship, stepmothers and -fathers - that was on top of the complexities of a normal relationship. Communication, intimacy, families, logistics, beliefs and values... just to name a few issues one dealt with when trying to form something healthy with someone. There was no way she was ready for any of this, and especially with someone as unpredictable and complicated as Tristan seemed to be.

Rory drove home from Hartford, feeling she was already ready for bed. She tended to doze off at odd moments during the evenings these days, like in the middle of watching Fleabag or trying to write her book which really wasn't going all that well. In that context, Rory was relieved to make it back to Stars Hollow in one piece, only yawning slightly as she stepped out of her car in front of her building that she was still just getting used to calling home. The streets looked empty, except for the Secret Bar that she could see in the distance with it's string lights lit, and a few of its patrons who were just heading home themselves.

She locked her car and searched for her house key. She was yet to find herself a keychain that she liked; hence it took her a while to fish the temporary small key ring with two keys on it out of her purse. Once she did, the keys slipped out of her clumsy fingers onto the street.

"Oh, man!" Rory muttered, bending down awkwardly to pick it up. Bending over was no longer an easy task, and she had to bend her knees awkwardly to do it.

"Rory?" came a familiar voice from behind her, causing her to freeze.

Her head popped up, causing her purse to fly around her body in a funny way by accident.

"Hey?" Rory asked, being unsure if she was seeing straight.

Logan stepped into the streetlight then, his hands tucked into his coat pocket.

"Can I come in so we can talk?" he asked, causing Rory's whole body to suddenly feel numb from both fear and anticipation.