Author's Note: I realize this has been done a thousand times before, but I wanted to give a go at what would happen if Rory ran into Logan in 2014.
Balancing your briefcase and an umbrella while walking through midtown New York City in the rain was already enough of a challenge, but doing so in her third best suit and a pair of pricey pumps was next to impossible. It didn't help her situation either that she'd spent 15 minutes trying to hail a cab before giving up completely, leaving her bag completely soaked and her bangs clinging to her forehead.
She hated visiting this city. New York had it's perks, of course, but she much preferred her life in Washington D.C. where she worked for Time Magazine as a foreign political reporter. But her expertise meant that she was often required to visit various morning news shows and panels for the networks. "Part of marketing the product, Rory." She hated that. The world was filled with stories that the world needed to know, but she also knew that they had a brand to withhold and she was just the one to carry the banner.
Just as the rain started to come down even hard, she heard the familiar ring of her iPhone. "Great." She muttered under her breath. Without glancing at the caller ID, she picked up the phone and scurried into a nearby Starbucks for refuge from the rain. "Gilmore."
"Kid, we've talked about this. No "Hi Mom." No "Mother, I'm thrilled to hear of your existence. No "Thanks for giving me life, oh caller." It hurts, Rory."
"Well forgive me for your daughter is turning into a drowned rat as we speak."
"Well, it's a good thing your interviews are over for the day before it messed up that perfect head of hair. I saw you on Fox News. The bangs looked great. I see you went with the ivory blouse. Not my choice, but hey, it worked."
"Mom, if it was up to you I would be wearing a neon pink Bangles t-shirt while Shepherd Smith and I discussed Syrian foreign policies."
"Oh to mess with Republicans. Are you on your way to meet April now?"
"I'm trying to. It's pouring, and I think the only way to get a cab would be to flash the driver, which would probably get me fired. She got out of class an hour ago, so we are doing early dinner at Rockefeller Center."
"Aw. I think it's super sweet and Walton-esque how sisterly that sounds."
"Well, she's been my step-sister for five years now. I think it's time to quit being shocked by us being nice to each other."
"Hey, you think you can slip in Thanksgiving into the conversation? We are still trying to figure out if she's coming here or to New Mexico, and while Luke doesn't want to pressure her, I know that he'd like for her to come and spend a little time with William."
"I will, but you know, I get it. She's 21, and her baby brother is 3. It's very Rory/GiGi circa 2005. The age difference is hard to forge deep bonds."
"How Dr. Phil of you. Well, see what you can slip in, ok? Don't drown! Call me when you land back home tomorrow."
And with that, her mother was gone. And Rory still had 5 more blocks to go.
It was Friday in the middle of a downpour, and all of none of the paths to Rockefellar Center sounded appealing to her, sans taxi. She quickly weighed her options and decided to take the route through Times Square. It wasn't the quickest distance, but given the time of day and the rain, the tourists might have escaped to some of the bigger stores and she could have the sidewalk to herself.
She was just approaching the heart of Times Square when she couldn't help but notice the huge stand being set up near the Good Morning America plaza. Construction workers continued to nail boards and use drills to set up the large metal structure and cameras were being set up under large tents and wide awnings. A group of PR and media types huddled underneath one of the large overhangs, and Rory couldn't help but be a little curious. It looked like a big announcement or product unveiling would be happening later this evening. She made a mental note to text her friend in features later. This might be something he'd want to know about.
Before she could get any closer to check out the media stunt, Rory was suddenly knocked down by an unexpected force in a black trench coat and gray umbrella. Her iPhone went flying out of her bag and into a large puddle of water and she heard the undeniable snap of her heel breaking underneath her. She herself had landed face down in the middle of a wet and overcast Times Square.
"Oh holy night. Do you think you could watch where you are going?" She began yelling as she started to get up. She quickly lost her balance when she realized that her precious heels were ruined. She felt Black Trench Coat reach around her arm to assist getting her back on her feet, and a sharp, familiar tingle went up her arm and down her spine.
"I'm so sorry, miss. I was texting and wasn't watching where I'm going. Here let me help you. I can go buy you some new shoe-"
The look of shock on Black Trench Coat's face matched hers identically. For there, in the rain on the wet November day in Times Square where hundreds of thousands of people had crossed that very spot that very day stood the one and only Logan Huntzberger.
"Rory Gilmore, as I live and breathe."
"Logan? What are you doing here?"
A smirk ran across his face, and she couldn't help but notice that he hadn't let go of her arm yet. "Obviously, I'm here to give you an excuse to go buy new shoes. Here, let me grab that for you." He quickly bent over to grab her umbrella that had fallen out of her hand and placed it over both their heads. "Rory, how in the world have you been?"
Still in shock she fumbled for words, "Oh um, great until I was mauled by you coming down the street going 60 miles an hour. I think that's illegal for a pedestrian. Wow. Logan, I can't believe this." She tried to smooth the wet hair on her forehead and attempted to hide the nervousness that instantly set in upon seeing his face for the first time in 7 years.
He chuckled. "Yeah, I'm sorry about the ambush. I'm running late to this app media release and obviously we knew the rain was a possibility, but I was texting my assistant to see if they were able to move this somewhere else. Times Square was a stupid idea, but investors want splashy. Someone booked Taylor Swift to launch this thing, and it has to go perfectly or else and…..and I'm rambling. " He smiled uneasily. " I guess I was texting and holding my umbrella at the same time and didn't see you there. " And he paused with a smile. "Of all the people in the world…"
She could feel the awkward tension radiating between them as they stood under the umbrella, together for the first time since his proposal 7 years ago. He was still so handsome, but older. His blonde hair no longer tousled, but combed in a respectable business professional style and he was dressed in a three piece suit that went well with his Black Trench Coat façade. Even wet, he still looked dashingly charming.
"Yup. Can't believe it." Pause. "Crossroads of the World." Yet another pause. "So, I probably need to go get shoes."
Brought back to reality, Logan reached into his pocket and grabbed his wallet. "Again, so sorry about that. Those looked like great heels too. " She noted the hint of flirtation in his voice. "So here's what we are going to do. I see you on TV. I know you're a D.C. girl now. You staying in the city tonight?" He pulled out a credit card from amongst a hundred others she saw in the fold.
"Yeah, but-"
"Got plans?"
"Just dinner, but I really can''t-"
"Take my credit card, go buy shoes for dinner, and then meet me at Penelope's for coffee at 9. You know Penelope's right? Lexington?"
"I can buy my own shoes, Logan."
"I know you can, but I feel horrible for killing those."
"But Logan."
"Those were great shoes. Let me help find a great replacment. It's just coffee. For old times sake. Of all the people in the world, you are the one I knock down in the middle of the busiest corner in the entire world. I think that means we owe the universe a coffee date, Ace. "
The use of the old nickname weakened her resolve more than she cared to admit. She hadn't heard that since the night of the proposal, and within an instant she was 22 again and watching him propose in front of all of her grandparent's friends.
"9:00. Penelope's. I'll be there as long as another black trench coat doesn't take me out."
He smiled at her as he opened up his own umbrella and headed toward the media event. "Perfect. And Rory, you've got the Amex Black Card. Spare no expense on replacing that heel."
And within an instant, he was gone, swallowed into the crowd and frenzy of the event set up. She stood there for a moment, wordlessly and shoeless, in awe that the past 10 minutes had actually happened.
She couldn't help but pace outside the restaurant. The rain had stopped and a sharp chill had entered the air, but the lure of coffee and the warm fire inside couldn't help convince her that she could go in. She couldn't do this. She couldn't see him. But she couldn't stand him up either. She still had the credit card he'd shoved at her, and she needed to return it. Who gives a complete stranger their credit card and trusts that they are going to return it? Only, she wasn't a complete stranger. She was the one he had ceremoniously dumped at her graduation ceremony.
She had tried to reach out to him only once. Despite being a social media entrepreneur and Internet mogul, he wasn't on Facebook. He didn't tweet. She'd tried to find him on Instagram once, but there was no account. He either didn't have accounts or he didn't want to be found.
Shortly after Obama had won the presidential election in 2008. Rory had been offered a position with an online magazine to cover the White House beat in during his first year in office. After a year and a half on the buses, she was thrilled at the opportunity to have her first single apartment and ride on the Subway and find restaurants that would become "her" places.
She found a great small apartment near Georgetown that was perfect, but she couldn't help but feel overwhelmingly lonely as she sat in the middle of the unfurnished and undecorated space filled with boxes and boxes of her things from storage. She started pulling out her knickknacks and whatnots; some things were items she hadn't seen since leaving her apartment with Paris and Doyle. There was her old Harvard flag that had lived in her childhood bedroom. The framed picture she kept of the Asher Flemming funeral flier.
And then, covered in bubble wrap, she saw it. The rocket. The one that meant Logan would wait in suspended animation for her.
And just like that, she broke down. She sat in the corner of her brand new-big girl-on-her-own life and cried with complete heartbreak.
She didn't know what came over her, but she pulled out her phone and dialed his number. She knew it was a long shot that he would even answer, but she had to call him. She knew it had been 18 months since they last spoke; he could be dating or engaged for all she knew. But she missed him more than ever at that very moment, and she needed him. Even if it was just a phone call.
She dialed the number from memory, as it had long been deleted from her cell phone. The number rang and rang and rang, and finally a female answered the line. "Palo Media Arts. Sharon speaking. How can I help you?"
Rory glanced at the clock on her phone. It was 7:04 EST, which meant it was 4:04 PST. "Uh, I'm sorry. I must have misdialed. I'm looking for Logan Huntzberger?"
"No, this is Logan's line. He's currently in a meeting right now. Can I take a message?"
"Well, I guess. If it's not a bother. Can you tell him that Rory called? Same number."
"Sure, writing it down. Thank you for calling." And just like that, the receptionist was gone. She sat there in the corner, praying that he would call her back.
But he never did.
For a week, she allowed herself to grieve. And then, on the first night the cable was installed in her apartment, a "Friends" rerun caught her attention. Rory sobbed as Monica told Richard, "Getting over you was the hardest thing I've ever had to do. I never let myself think about you."
And with resolve, Rory lived her life under that rule. She never allowed herself to think of Logan.
That is, until the Black Trench Coat broke her shoe.
She waited until exactly 9:07 before she pushed open the door of Penelope's. She saw he was already sitting at a corner booth with a tablet and a phone at his table, working both with fervor. He glanced up at the sound of the bell ringing and waved her over.
"I was afraid you were going to take off to D.C. with my Amex, Ace. I was looking up Olivia Pope's information as we speak to find you. Just give me two seconds. I'm wrapping up a few interview questions for my media VP." He continued to type feverishly. "And… done."
"You're a busy guy, Huntzberger. How's T. Swift? You didn't cause her to write any new bad boy songs this evening, did you?"
"Ha. No. I think there's a couple about me on the last album though." He joked as he put his tablet in his briefcase. "So you find your shoes, Cinderella?"
"Yes. I mean, I bought my own shoes, Logan. I'm returning your card with zero swipes. You were very kind to….well….force it on me earlier."
"Hey, I know you can afford your own shoes, Ace. I know you are a popular girl these days. I've read your stuff. You are still one of the most talented writers out there. The piece you did on the Russian financial system last spring was one of the best articles I've read in a long time. I wasn't surprised when it won the Berkley award."
She sat there, looking at him with shock and awe. "You follow my work?"
"Ace, how could I not? You're everywhere these days. Liberal and conservative media both love you, and you are telling really unique stories. I saw you on "Meet the Press" last month. Fantastic debate. It's my job to follow that kind of stuff."
She couldn't help but feel a bit disappointed in his response. He followed her work from a completely platonic and journalistic perspective. She tried desperately to shake it off. Too much time had passed for her to expect anything more.
"Yeah, well. I do what I can. I love the travel and the writing and seeing what the world has to offer, but I really hate all of the glitzy press stuff. I enjoy the debate on the panels, but I can't help but feel like I'm pushing some sort of media agenda each time I go on one of those talk shows."
"Hey, but Amapour had to do it. It's part of the territory. And you're good at it." He took a sip of the coffee the waitress put in front of him, black with one sugar just like 7 years ago. "So when does your book release?"
Shocked, she began to stutter. "How do you know about that?! Logan, seriously, I….I just turned in my final edit to my editor. They haven't even released the details to anyone yet, not even the PR teams." She started fumbling for her phone in her bag to text Jenny at the office, but realized it was still in its watery and un-working state from earlier.
"Ace, it's my job to know these things. That's what I do, remember?"
"Logan, stop. What DO you do besides inspiring Taylor Swift ballads? How do you know everything about everyone? Are you suddenly the FBI's publicist? And why are you here in New York, Logan? Why aren't you in your precious California? And how do you know about my book?" She couldn't hide the frustration and demand in her voice.
He gave her the smirk that both frustrated her and made her swoon. "Palo Media went national five years ago. With a couple of investors, I bought it out from the other partners, and it's now Huntzberger Media Arts, or LH Media due to a fun ''copyright infringement" lawsuit from "Daddy Dearest." He emphasized his frustration using air quotes. "The company mainly backs app developers but we also use social media to publicize new movies, music and yes, even books to add to truly organic marketing concepts. We opened satellite offices in New York and Atlanta, and I've been heading up the projects here. It's a really interesting time to be in this business. 2015 will be huge for new media platforms."
She could tell he was passionate about his work. She always knew he'd be a true work dork once he embraced something that he loved. She thought he felt the same way about her once upon a time too.
"So is that what this is about? You saw me today and took that as an opportunity to talk to me about my book? What kind of app could you possibly build in regards to my assessment on Bengazi?"
"I don't follow your career because of business, Rory."
The awkward pause returned, and she could tell he was seriously contemplating his next question.
"So….those new heels you bought for your dinner. Was it a meal with someone…..special?"
"Logan, not that it's any of your business, but I was having dinner with my sister. I mean, my step-sister. April. You remember Luke's daughter? She's in school at NYU. She's so smart. She got a full scholarship. She's going to be a doctor."
"So your mom and Luke finally got married. How 'bout that?"
"Yeah, and they have a son. Will turns 4 next year."
She wasn't sure she understood why, but a pained expression covered Logan's face. He stared at his coffee cup for what seamed like eternity. "Four. Wow. "
"What, Logan?"
He took a few extra seconds before he said, "So much has changed. You've got a sister and a brother and this great job where you are a freakin' public expert on government and politics and I'm super impressed, but all I keep thinking about are damn avocado trees and what would have happened if you'd just said yes."
There it was. He'd laid it out on the table. She looked down at her watch. It had only taken 23 minutes exactly for the elephant in the room to start his headlining act.
Pissed, she fired back. "Logan, you walked out on me. You gave me no choice or say in the matter. At all."
"That's bull, Ace. And you know it. I asked you to marry me. You had a choice, and you chose no."
"That's not a choice, Logan. That's an ultimatum. I still don't think you've ever truly understood the definition of the word. Me telling you I couldn't be "one of the many?" Not an ultimatum. You saying that it's either marry you or game over? That my-smart-but-stupid-charmingly-ignorant-explanation-hating-chum, is the definition of the word."
"Charmingly ignorant?" He couldn't help but smile at the familiar tone of her rant. "I assume that's better than butt-faced miscreant."
"Only slightly."
As the waitress came by and handed them the check, Logan placed the returned Black Amex in her hands and looked straight into Rory's eyes. She'd forgotten just how beautiful and soulful his deep brown eyes were. "Answer my question."
"Which one?"
"Is there someone special?"
"There are lots of special people in this world, Logan. My mom, the vice-president, Dolly Parton, the intern who makes the good coffee at the office, my—"
"Rory."
She crossed her arms across her chest. "No. There's no one special."
The grin was undeniable. "Look, you hurt my feelings deeply by not letting me buy you shoes. You owe me due to the sharp blow my ego took by you not taking me up on my overly generous offer." He paused, and the grin slowly turned serious. "And I don't want to fight with you. Not tonight. What started out as a really crappy day ended up being one of the best days I've had in a really long time because I ran in to you. Literally ran in to you. And while I hate your shoes are ruined, I am so glad to see you again, Ace. And I don't want to fight; not now."
"Well, what do you want then?"
"I want to take you to dinner. Tomorrow night."
"I'm headed back to D.C. tomorrow. My flight leaves at 3."
"Well, change it. Tomorrow's Saturday. I know journalists never sleep, but I'm pretty sure the world is quiet enough right now for you to take a day off."
He grabbed her hand across the table. "Take a risk, Ace. Be spontaneous. I know you've interviewed kings and world leaders and you've been in dangerous situations that makes my whole being hurt with worry. And even though I know you probably never think of me anymore, I can't help but think of you. Every damn day. Yes, I read your articles for business, but I also read them because you are the single biggest influence on my life and it helps to know what you're up to and what's going through that brain of yours and if you are safe. I wake up and wish that I had just said "sure" when you said you needed more time. But I didn't. And I know that we have things to talk about and that Rome wasn't built in a day, and this can't be either. But I'm begging you. Just have dinner with me. I was meant to run into you today, and you know it. Just have dinner with me, Rory."
When his rant was over, he looked at her expectantly. Her answer had to be no. This was not part of the plan. She'd left Logan Huntzberger behind years ago. That door was painfully closed shut. She had worked too hard to heal and forget. Spending more time with him would just reopen all of those old wounds.
She opened her mouth to say no, but her heart took over. Quickly and then all at once, impulse took over her very being. "I guess I could see if I can change my flight and extend hotel reservation."
"Go. Change it. If they give you grief, I'll book the extensions myself."
She grabbed her purse and stood up from the table. "I think I need to go, Logan. Do you want my number?"
"Is it the same as it used to be? I still have that one."
She suddenly felt herself slip back to the self-conscious girl who cried on the empty apartment floor. "Are you sure? Because I called you once….and you never called me back."
He quickly stood up to meet her stare. "You called me? When? Rory, I swear I never got the call." He grabbed her hands again. "I would have called you back. A hundred times over, I would have called you."
She couldn't deny the chemistry she felt when he grabbed her hands or the relief she felt knowing that she'd been on his mind all these years. "It doesn't matter any more. I'll grab a new phone in the morning. Text me the details and I'll confirm tomorrow." And from the same spot in her heart that said yes to his invitation, she stepped closer to him and hugged him as if she would never let him go. And to her complete happiness, she felt him do the same as his arms wrapped tightly around her waist.
"I've missed you, Ace." He whispered in her ear.
"I've missed you, too. I'm so glad you killed my shoes."
