When Judy met Jen

Dead To Me (TV)
F/F
G
When Judy met Jen
Summary
A when Harry met Sally AU. Jen's boyfriend bails on her and asks his coworker to drive with her from Chicago to New York. 18 hours in a car with a stranger isn't exactly Jen's idea of paradise. Especially when they don't really seem to get along. But the unlikely pairs paths seem to cross in ways that make Jen rethink whether there is such a thing as destiny. And this stranger isn't too bad once you get to know her.
Note
yesss when harry met sally is my favourite movie. basically if you havent seen the movie, im gonna start with jen being in her mid to late twenties and judy in her early twenties and we will see their relationship progress over these coincidental meetings through the years.
All Chapters Forward

Harry Styles, now there's a man we can trust

"I think you'd make a great mom."

"Really?" Judy seemed genuinely surprised, as if she wasn't the single most kind and loving person on planet earth. Jen nodded matter-o-factly, reaching out ahead of them to open the door for her as they walked out of the gym right next to Judy's apartment. "That's sweet of you."

"It's not sweet if it's just the truth." Jen noted, but Judy's raised eyebrows and a grateful smile shut her up quickly. "You wanna order in?" Jen turned to the direction of Judy's apartment, which by now was very familiar to her.

"Sure." Judy agreed. "But wait..." Judy held onto Jen's arm, in an unnecessarily dramatic fashion. "I'm vegan now. So we need to order from somewhere with vegan options."

"Noo Judy. Since when?" Jen's groan really honed in how pleased she was with Judy's life path.

"Since I watched that documentary about climate change last week." Jen could vaguely remember a very emotional phone-call about the subject a week before. "Polar bears have already lost so much. I don't think being vegetarian is enough to save the planet."

"I don't think you alone can save the world."

"So you'll join me?" No fucking way.

"I..." Jen had been just about to say hell no, before making the mistake of looking into Judy's genuinely hopeful eyes. She looked away but knowing Judy was excitedly waiting to hear her say yes, really fucked with Jen's head. "Maybe I can eat less meat or something." Jen groaned, but her eyes were gleaming, still fixed on Judy's bright and hopeful smile. "But I'm not going full vegan."

"The polar bears are eternally grateful Jen."

"I don't think their thanks are what I care about."

"Thank you, Jen." Judy leaned in to give Jen's cheek a playful peck, before turning around to face the door of her building with her key ready.

Jen gagged at the sign of affection as soon as Judy's eyes glanced back at her again, but once she was walking far enough ahead and Jen's face wasn't visible to the brunette, she couldn't help but bask in the warmth of the blood rushing in to her face.

---

"I don't get why anyone would ever cheat on you." Judy sighed as she nonchalantly played with Jen's hair as they sat on the couch watching The facts of life.

"Yeah, well I think you're as kind and caring as humainly possible, so I'm not feeling very special here." Jen brought the wine glass to her mouth, trying to find some clarity on what to make of the growing touchiness of Judy. She didn't mind it necessarily, it was just new, different. But then again, this was most likely how normal female friendships free of resentment were all about.

"You should!" Judy brought her hands to the sides of Jen's head and pulled her back enough to form that mandatory eye contact that Jen so hated. It didn't feel confrontational, but it was uncomfortable none the less. "You should feel very special. You're very special."

"Thanks." Jen said, not quite meeting Judy's intensely appreciative eyes. The blonde found it best to just go along with Judy's whims and she did find they eventually came to an end.

Judy booped Jen's nose unexpectedly, the brunettes giggle lifting up a world of worry off of Jen's shoulders, until it came crashing down on her again once Judy gently nudged her to sit up straight again, and the familiar hands were no longer exploring her hair.

Jen leaned back against the couch again, sitting for a bit in the comfortable silence surrounding them, listening to the faint noise of the tv.

"I wasn't a very good girlfriend you know." Jen said, not looking away from the tv. She could make out Judy turning to her from the corner of her eye, but she didn't want to have a conversation, to bare herself raw, she just wanted Judy to know. "I was working a lot. I didn't really have a lot of time for him. And I don't know if I even wanted that. To make time for him, you know?" Jen turned to Judy now, for reassurance, and found the brunette furiously nodding, supporting her fully. "I'm kind of better of alone. I've been with jerks, I've been with nice guys... never works out."

"It will. I promise you it will." Judy shifted in her place and reached out to hold Jen's hand. "You'll find the right person at the right time and it will work out."

Jen laughed a little at Judy's blind faith, annoyingly persistent optimism that things would work out, despite the fact that life kept fucking her over time after time.

"I hope so."

------

" Breast cancer. "

"Oh my god, that's horrible. I'm so sorry for your loss." Judy was taken over by such grief that Jen really seemed like she was handling this like a champ right now. Or an asshole.

"Judy, it's been like 15 years, don't you think I've moved on by now?"

"The death of a parent... I mean that's got to stay with you forever.” Judy was talking generally of course, not meaning to poke at old wounds. Yet.. “ Some life-long trauma right there."

"Oh gee thanks." Jen scoffed at Judy's over exaggeration. Jen was most certainly fine.

"I didn't mean..." Judy winced a little at Jen's harsh tone.

"It's alright. I know what you mean." Jen softened. Usually she quite enjoyed making people squirm a little, feel intimidated, but she didn't want Judy to feel anything but safe and cared for in her presence. Friendship.

"I don't think I've seen my mom in like 10 years, and it's definitely affected me. I just don't have faith that I won't make the same mistakes she did. I want kids so badly, but I probably need closure before I can do that."

"So call her? Do you know where she lives?" Jen suggested as she took another bite of whatever vegan decoction Judy had cooked for them. Not to bad. At least it was made with love.

"She's in prison." Judy mentioned it like one would lament about a fallen omelet or a ball in a tree. Oopsie, my bad.

"Well fuck. What the fuck did she do?"

"Drugs." Judy continued on in her nonchalant tone, but her uncharacteristically short responses told Jen that this was a sore spot.

"Sorry about that." Jen gave Judy a tight smile, a horrible attempt at comforting really, but Judy took it gladly.

" It's alright."

"Those pesky mommy issues, huh?" Jen chuckled a little, chucking down her third glass of wine like it was nothing as if to somehow prove that she was strong and capable, but the choice of putting all that motivation into drinking and road rage, instead of something useful, only ended up saying the opposite. Deep damage was done to this woman, beware.

" They are a bitch." Judy agreed, her voice light, but her eyes sad.

"You said it, sister."

----

"How was it?" Were the first words the came out of Judy's mouth once, Jen walked out to the parking lot of her very fancy new office building. Lorna's fancy new office building. They were moving up in the world. As a company. Jen wasn't sure if there was a ball a chain tied to her foot, but she didn't think it was possible for her to go up at the moment, only sink down.

"Eh. Same old, same old. Not sold by the fancy nut milk options and the modern furniture." Jen took her place on Judy's left side and too started walking down the street to their favorite càfe. "The chairs are pretty uncomfortable. Four microwaves?Excessive."

"You're just looking for reasons to complain now." Judy had that pep in her step that somehow managed to make an appearance even when the rain was pouring down on them, or it was a day as cold as ice. Jen tried to mimic it, hoping she might get the brunette's curiosity and optimism that most certainly had everything to do with the light bouncy steps that she took to keep ahead, and not the mindset buried in her brain. She looked up at her friend to see her smiling and returned the gesture.

"I think it's going to be a good day."

"It's raining later." Judy said, not to depress Jen, but maybe to offer her a challenge.

"We could cook and watch Facts of life." She passed. "Or sit in our respective apartments and wallow in despair."

"There it is."

" I personally prefer the first one." Jen said, lifting her head up high.

"Oh! Does moping around have a challenger?" Judy joked, carefully poking Jen to test the waters.

"What can I say? I might have a soft spot for brunettes." Jen responded, taking part in the poking fun, it certainly did make her feel better, than repressing all human emotion.

"Oh, I know." Judy hummed knowingly.

"Don't." Jen warned her.

"Harry Styles, now there's a man we can trust." Judy was fighting laughter, reminded of a very drunken night spent with Christopher and Karen, watching a Behind the album documentary carefully chosen by Karen.

"He seemed like a charming guy that's all."

"Trust me, I get it. I just didn't peg you for such a cougar." Judy rawred, as it was obligatory, when using the word cougar after 2010. There had to be a punishment to fit the crime.

"Oh shush." Jen pushed Judy away playfully, but held onto her lightly to pull her back by her coat, just in case a group of aggressive bikers decided to completely take over the lane next to them. Better stay safe than sorry.

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