Hello and welcome back to another installment of "Finding Gilmore"! Thanks to every one who has been keeping up with this story, and thanks to those who have followed it and reviewed. It means a lot that you are enjoying this just as much as I enjoy writing it!

I'm really excited to get this chapter out to out to you all because we're finally going to get some of Richard's POV and what's been going doing at Yale. Also, there were some questions I wanted to go ahead and answer here about previous chapter characters and what not. For the most part, several of Richard and Emily's friends are original characters of mine that I decided to add because, apart from the little facts here and there about young Richard and Emily in the show, we don't know much about who they hung around and what they were really like as college students. So I decided to just add in a cast of characters that they may have hung around, so I hope you guys like them as much as I do!

Anyway, on to the story, and I will see you all down below!

Chapter Three:

September 5th, 1963

Dear Richard,

I am so glad to hear that you are all settled in and are prepping for what I'm sure will be another great year at Yale. I'm just sad that I won't be able to be there for the first three months with you. As you already know from the numerous letters I've sent you since I left, mother still has me gallivanting across Europe with her ever since the…divorce. She's doing better I think. Thank you so much for your concern in your last letter, Richard. It really means so much to me that you are still so willing to stick by my side even with this dreaded situation with my mother and father. It's not the best way I wanted to usher in our engagement—being apart for three months and having to relay messages between my warring parents because they refuse to speak to each other.

I know though, that our engagement is the bright spot in all this terrible trouble my parents are causing for us. I miss you terribly every day and cannot wait to come home and see you once again. I know the last night I saw you wasn't ideal. Hopefully you were able to procure a new set of glasses. I really wish that girl hadn't broken them, they were my favorite pair on you.

Mother and I will be settling in to our hotel in Milan soon, so make sure to send me recommendations of your favorite restaurants that we absolutely must visit, because I know how much you love this city.

I'll keep this letter short, I'm writing you from a beautiful outdoor café and mother has had one too many glasses of champagne and is currently about to take the waiter home with her.

I love you Richard, and I am counting down the days to when I finally get to come home. And to answer your question in your last letter, your mother's ring is still nice and snug on my left ring finger and I have every intention of keeping it that way.

I will see you soon my love.

Always yours,

Pennilyn

I look over the letter I last received from my fiancé, Pennilyn Lott, who had been whisked away by her brokenhearted mother exactly one month ago, and I can still feel the last kiss I gave her as I said goodbye to her at the airport. As much as it saddened me to see her go just two weeks after I proposed to her, I still believed that the absence would make our hearts grow fonder of each other. And even though I missed her every single day since she left, I was adamant about the fact that the separation would be good for us.

A challenge, I told her as I left a trail of soft kisses on her tear stained cheek as I dropped her and her mother off at the airport.

"A challenge indeed," She said as she picked up her carry on item and grabbed my hand, squeezing it tight before walking away and leaving me for what would be the longest four months of our lives.

But, I told myself as I got into my car and drove away from the airport, that if there was one thing Gilmore's were experts at, it was taking on a challenge. So I was determined to make it through the last month of summer without her, as well as through the first three months of my junior year at Yale without her as well.

"Still wallowing over your long lost love Richard? May I remind you, she hasn't been shipped off to war?" The door to my room opens and I turn to see my roommate making his way to his cluttered desk with a newspaper in hand.

"Yes, I am aware that my fiancé is not going off to war Michael, but it still doesn't help that she is abroad while I'm stuck here with the likes of you."

Michael, my roommate since my freshman year at Yale, grabs his chest in jest, as if my words have cut him to the core.

"Oh Richard, your words hurt me so! How will I ever recover from your poisonous verbal darts," Michael exclaims in a passionate and broken hearted tone before he flings himself on to his messy bed.

Michael Seymour Campbell, ladies and gentlemen. You might mistake him for a Theatre Major, but in fact, he was a Business Economics major and my best friend here at Yale. Michael may not have been the greatest looking gentlemen in our building—a head of messy blonde hair, a bit of a jolly belly, and the palest skin that would burn at the smallest exposure to the sun—but what Michael lacked in looks he made up for in charm and charisma. Michael and I were very much a dynamic duo here at Yale ever since we first met, and we had no plans to change that, seeing as we always got along and were very partial to the same type of whiskey on Friday nights.

"Richard, this is the time to be free my friend! How long have you and Pennilyn been an item? Almost a year now? Now, I'm not saying to let yourself stray from the sacred road towards marriage with the lovely Pennilyn, but I am saying now is the time to loosen the reigns a little. Go out more! Meet some new people, preferably some beautiful young women, not for you of course, but for me, so that when Pennilyn comes back, I don't have to have awkward dinners with you and her in the dining halls."

"Michael, you do realize that those dinners are only awkward because you invite yourself to them, even though I have clearly stated multiple times that those are dinner dates with my fiancé."

Michael sits up, grabs the newspaper from his desk and begins to peruse the pages so that he doesn't have to answer me.

"Michael?"

My roommate sighs, sets the newspaper down, gets up from the bed and begins to pace across the room. His checkered shirt tail is sticking out in the back and I can see that he is about to embark on another one of his monologues about the most beautiful human in the world…according to him. Michael grabs his chair and scoots it over to where I'm seated and takes a seat with a very serious look on his face.

"Richard, you have to tell Pennilyn that I am in love with Lilian. Absolutely in love with her. I can't help but crash your dinner dates with Pennilyn, because it's the only time I get to hear about how Lilian is doing. They're best friends Richard! And Lilian, beautiful gorgeous Lilian, doesn't even know I exist!"

I turn my seat away from Michael and focus on the letter I was about to write back to Pennilyn before I accidentally opened the floodgates holding in all of Michael's love for Lilian Aster, Pennilyn's best friend and confidante, and also the only woman Michael has ever been so-called "in love" with.

"Richard don't ignore me like this! My heart is in absolute agony! Without her, I am nothing!"

"Jesus Christ Michael, calm down. She's just a pretty girl who comes down every other weekend to visit. And may I remind you, she does know you exist. Didn't she ask you to help her with her homework that one time?"

I can't see Michael's face, but I'm more than 100% sure that his eyes have glazed over with love and is thinking about the one time he spent a full hour and a half in Lilian Aster's presence because she was having trouble in one of her Math courses at college and asked him for his tutoring services. I'm not sure the poor girl learned anything of substance though. Michael had a tendency to stutter and fall over his words when he was in the presence of a pretty girl without any alcohol in his system.

"Ah yes, that was the day I knew Lilian Aster would be my future wife. Of course, I didn't make the greatest impression, but just wait until she sees me next time she comes down from college. I will sweep her off her feet."

I try to hold in the laughter that is slowly crawling up my throat, because if there was one thing I knew Michael wasn't capable of doing, it was expressing his feelings coherently towards Lilian, who by the way, was one of the sweetest people in the world and more than likely just felt bad that Michael had a stuttering problem…even though he didn't—he literally just could not talk to Lilian.

"Mark my words, my friend. Lilian Aster will fall in love with me. Which is why I need you to make more friends with the ladies. I need a young woman on my arm so that the next time Lilian sees me, she'll realize that I am on the verge of being taken, and will have a grand epiphany that she does, in fact, love me."

"That is by far, the stupidest plan I have ever heard in my life Michael," I reply and continue with my letter.

"Well, what else would you expect from Jolly Mikey?" I am so engrossed in my conversation with Michael, I don't notice the door to our room had been open, and that someone is leaning in our doorway with a big cocky smirk on his face.

"Henry," I say, trying to mask the disdain in my voice, but doing a terrible job at it. "When did you get back?"

Henry DuGrey, perhaps one of the most irritating humans I had met during my time here at Yale, was definitely not someone I wanted to see in this building, because it meant that Michael and I would have to endure his presence for the rest of the year. And to be fair, Michael and I did try everything we could to get along with Henry. Our families ran in the same circles and we were always invited to his parties—the official and unofficial ones at that—but Henry was what I liked to call an old fashioned "playground bully". Ever since our freshman year, Henry always had it out for Michael. Maybe it was because of his weight or the fact that Michael could make friends more easily than Henry ever could, I don't know, but Henry always made sure to make Michael feel inferior every chance he got.

"Well Richy, if you must know, I just got back this morning," Henry replies to my not-so-sincere question. "Mom and Dad were nice enough to send me on a trip to New York just before school started so I could tour the town and see where I would be interning during Christmas vacation."

I nod my head and move towards my bed, so I can finish unpacking and hopefully signal towards Henry that our short conversation is over.

"So Mikey," Henry begins his normal tirade against my roommate, and I cringe at the irritating nickname Henry has given to Michael because everyone who knew Michael understood that he hated when people shortened his name. "How was the summer pal?"

"It was fine Henry," I can hear the curtness in Michael's voice and I know that if Henry isn't careful, Michael might blow a fuse.

"Nothing big to report? Nothing of grand importance maybe? No chubby news coming from the south side of town Jolly old Mikey?"

"Henry that's enough, you can leave now," I say as I grab Michael's shoulder just in time to try to keep him seated so he doesn't fly at Henry and give him a black eye.

Henry laughs in a mocking tone and saunters his way out of the room. "I'm just kidding with you Mikey, no need to get too worked up over nothing. Just wanted to see how you were doing is all! But I'll leave you and your wife alone. Don't want to cause too much trouble in paradise. Until next time boys!"

I can feel Michael shaking from anger at seeing Henry again, and when the door finally closes I let go of my roommate who I believe will not be jumping out of the chair to clock Henry DuGrey in the face anymore.

Michael scoffs as he gets out of his chair and walks to his closet door looking for what seems like a coat and hat. "That guy is the vilest human being I've ever met in my entire life. Gets his kicks out of trying to get a rise out of me and for what? Yeah, I know I'm big, but that doesn't change the fact that people like me more than they like him. In fact, the only reason people tolerate him is because he throws great parties and provides the best alcoholic brands from his dad's liquor cabinet. Without that, he'd be nothing." Michael finds a black coat and a hat to match and then takes out a cigarette case from his pant pocket.

"He's a bottom feeder Michael. We all know that to be the case. Where are you going?"

"I'm headed down to Iris' Pub to meet up with the twins and Percy. Want to join? We won't be out long, but pints are half price on Tuesdays."

"I'll come with you. I don't want to deal with Henry by myself if he decides to come back for another go."

Michael is about to step out of the room so he could light his cigarette. "Knowing him, he'd probably only care to come back if I was around so he could poke fun at me some more. It's a wonder that sweet girlfriend of his bothers to stick around with him. She's either just as bad as he is and we just don't know it, or she is too saintly to see how big of a skuzz he really is."

I grab my coat hanging from my desk chair and follow Michael out of the room and make sure to lock up before heading out to Iris', the local pub frequented by the majority of us students looking for cheap beer and a place to meet up, drink and talk.

Michael and I walk the path down to the pub in silence, the only thing passing between us is the soft sounding 'swoosh' of Michael's cigarette smoke. Smoking wasn't really a big habit of mine, but I did enjoy a cigar every now and again during social gatherings and parties. Michael on the other hand, was an avid smoker, mostly due to the stress of his courses as well as his family life back home.

The sun is just about to set and I know that the onslaught of fall courses is just around the corner, but being by my best friend's side, about to meet three of our other pals over a pint is just enough to keep my panic sedated. Going to Yale truly was a blessing and a curse at times. Although I loved every minute of my time here, the rigorous course material and the stress of always being at the top of the class was enough to cause a few migraines throughout the year. Michael had his way of coping of course, but unfortunately mine was thousands of miles away in Milan, enjoying the Italian wine and sun.

~O~O~O~

Iris' was filled to the brim tonight—as it was on most nights—and finding the twins and Percy was a bit tougher than I thought it would be. When we finally found them, things were as we had predicted on our walk over: Percy was chatting up a beautiful blonde at the booth, and the twins were drunkenly arguing over who the better-looking twin was—answer: it was definitely Marcus.

"Marcus, Finn, Percy. How are you boys doing tonight?" I yelled over the noise and found a stray stool to sit on while Michael awkwardly leaned against the small table we were all trying to occupy in the corner of the pub.

"Richard, tell my brother I am the better looking of us two. He still doesn't believe that I pull the most birds out of the two of us," Marcus says and picks up his pint to chug the last of his beer.

"Oye, Marcus, don't call ladies birds. It makes you sound more stupid than you already are," Percy says from the booth. He turns back to the unnamed blonde and grabs her hand and links his fingers through hers and gives her the Percy Travers smile that makes all the girls swoon. "Sorry darling, my mates over here don't know how to properly act around a respectable woman such as yourself."

"It seems like Percy hasn't skipped a beat since being away," I say to the twins who are bumming a cigarette from Michael's stash.

"It's that damn English accent of his. No one can resist that charm. You hear me darling?" Marcus shouts at Percy's blonde haired friend and waves his empty pint in the hopes of putting more emphasis on the words slurring out of his mouth. "It's just the accent talking, sweetie! Sooner rather than later, you're going to find out that our dear friend Percy here is a mere mortal just like everyone else in this pub!"

The blonde looks over at Marcus with a disgusted look on her face, mumbles something quick in Percy's ear, and gets up to walk back to what seems like a group of her friends standing next to the jukebox on the other side of the room.

Percy, not too happy with this turn of events, reaches out over the table and smacks Marcus over the head. "What the hell was that you idiot! I almost had that bird!"

Marcus, looking happy as a clam, steals his brother's pint and drinks. "Now, now Percy. What did we say about calling ladies birds?"

"Oh shut up you git," Percy says as he turns his attention towards us and away from the lous and drunk Marcus. "Anyway, Michael, Richard. Glad you could make it out. How were your summers?"

Percy Travers and the twins, Marcus and Finn Hampton, completed our close group of friends here at Yale. The twins hailed from New York, so it was rare to see them outside of school, and Percy was an international student from London, England.

"Ours were pleasant enough. How was yours," I reply back.

"Oh come on Gilmore, don't be shy about it! We all heard through the grapevine that you finally asked Penny for her hand in marriage" Marcus says and clinks his brother's pint—now his—with the empty cups scattered across the table.

"Marcus, do you always have to be so…loud," Finn says in an irritated tone from the corner of the booth.

The Hampton twins were as opposite as opposites could get. While Marcus was loud and prone to more alcoholic blackouts, Finn was more stoic and a man of few words.

"Oh…I'm sorry brother, I didn't realize we were in a library. I'll make sure to keep my noise levels at a minimum so I don't lose my reading privileges!"

"You always do this. You make a scene and then Allister comes out from behind the bar and kicks the both of us out because he can't tell us apart!"

The twins are back at it, which means all is well in the universe.

Percy rolls his eyes and looks at Michael and I. "So, boys, apart from dealing with these blokes all day, my summer went well. And Richard, I'm happy to hear that Pennilyn said yes. That is a big step for the both of you."

"Thanks Percy, that means a lot. It's just a bit of a drag seeing as she's been gone for the first month of our engagement, and she'll be gone for the next three months as well."

Percy flags over one of the workers and asks for a pitcher for the table. "Well it's just four months Richard. You two have been together for longer than that."

"That's what I keep telling him, Perc, but he won't listen. He's been wallowing over the last letter she sent to him over the summer," Michael says as he stamps out his third cigarette of the night in the ashtray at the table.

"I have not been wallowing!" I object.

"Richard, if I hadn't walked in when I had today, I'm pretty sure you would've been in tears over that letter."

Percy smiles and pours me a glass of beer before I have time to decline the offer. "That's true love Richard. Don't deny yourself that. Pennilyn is a beautiful girl, I'm sure she misses you just as much as you miss her."

I take a swig of my pint, and nod in affirmation, because it would be too much to even talk about why I was really spending so much time with that letter today.

~O~O~O~

After dropping off a very inebriated Marcus and a very sober Finn off at their rooms, we say goodbye to Percy and headed back home in the cold September night. The air outside is blowing through the trees and I'm calling it now: this was going to be one of the coldest winters here at Yale.

"The boys looked good. Apart from Marcus of course, he's always sloshed by the time we get to the pub,' Michael says between chattering teeth.

"Yea, they all looked the same to me. Percy is still the biggest flirt, Marcus is still the biggest mess and Finn is still the biggest cynic."

Michael laughs at my description of our three close friends. "And then there's us. We make a good group of idiots don't we?"

I smile and watch my breath become white wisps in front of me. "That we do."

There's a bit of silence before Michael attempts to say something more. "Is everything alright Richard? You've been…quieter as of late. I was just wondering if there was anything wrong that you wanted to talk about." I can hear the concern in Michael's voice and know that if I were to talk about it now, it would only bring up more questions than anything else and tonight, I just wanted to get back to our room and sleep.

"There's nothing wrong. I'm good, believe me."

Michael pats my back and thankfully that is the end of a conversation I was really not up to having ever.

~O~O~O~

August 2nd, 1963

The night was hot.

Unbelievably hot.

As much as I enjoyed nights out like this one with my girlfriend Pennilyn, this night in particular was one that made me regret wearing a suit and tie to another one of Henry DuGrey's parties. I was standing at the landing of the stairs, nursing a cup of beer while I waited for Pennilyn, who was currently using the ladies restroom. Michael had stopped by to say hello and was now rummaging through Mr. DuGrey's office, looking for the best cigars to smoke out in the backyard.

Nights like this were always a normal occurrence when Henry's parents were away on business, and luckily for me, Henry would soon be making his way to his dad's liquor cabinet and taking out the finest whiskey American money could buy.

"Sorry to keep you waiting darling. I went upstairs to find a bathroom and all the doors were locked, so I had to come back down and wait in the longest line known to man, but hopefully you didn't miss me too much." Pennilyn took my hands in hers and reached up on her tippy toes to give me a sweet kiss on the cheek.

Pennilyn Lott was perfect in every way one could ever hope for. She was beautiful, smart clever, and fortunately for her, my mother loved her probably more than I did.

We were a match made in heaven.

And yet…as I held her hands in mine and looked at her beautifully perfect white smile and deep blue eyes, I could feel something telling me that something was…missing.

Now, I didn't want to worry my beautiful girlfriend, because when it came down to it, we had been together for over a year now, and this feeling that I had was most likely temporary, but I could almost feel it in my gut that the way she used to feel to me when I first started going steady with her was not the way I felt now. I still loved her of course. There was no doubt about that for one second, but for some reason, I still felt like there was a hole somewhere in me that Pennilyn was supposed to occupy, and yet…she wasn't.

"Is everything alright Richard? You've gone a bit pale," Pennilyn reached out to grab my cheek, but before she could make contact with my face, I felt a gust of wind and a body crash in to me as it came barreling down the stairs. In the process of this person crashing in to me, my glasses fell off my face and I could hear them shatter underneath the weight of this person's shoe.

Everything was a tad bit blurry now that I couldn't see properly, but what I did see was a young woman in a black dress, and she was crying. Her black hair was in a bit of a disarray, and yet her curls framed her face in a beautiful hectic mess. I tried to reach out to her to see if she was alright, but she looked frantically up the stairs and then back to me and quickly turned away from us and ran through the crowd of people towards the front door.

"Hey! Come back! You broke his glasses! How dare you run away without even asking if you can pay for new ones! Richard are you alright?"

Before I could answer Pennilyn, I stepped off the staircase and tried to follow the girl who had been crying. I don't know what compelled me to do so, maybe it was because I wanted to see if she was alright and that she wasn't hurt, but something inside almost coaxed me to follow and see what had made her so upset.

I opened the front door that she had just ran out of not a few seconds before, and even though my eyesight was still blurry, I could see her running across the street to the left and away from view.

Odd.

I knew that in the grand scheme of things, I would probably never see this young woman ever again, but I hoped that she found her way home safely and that whatever she was crying about would get solved immediately.

As for the other thing that was beginning to warm my heart, I knew that the second she crashed in to me, it felt like lightning had struck, and her touch, although brief, was like breathing in air after being under water for too long.

I don't know who she was, or what she was doing here tonight, but the inclination to find out was making me more and more uncomfortable by the second.

"I'm so sorry Richard. I don't think there's any way to repair these," I heard Pennilyn's voice behind me and she grabbed my hand in hers and still…I felt nothing.

Not one single spark.

In an effort to put those thoughts far far away where I couldn't see or hear them, I grabbed Pennilyn by the shoulders and hugged her to me. I planted a kiss on the side of head and closed the door in front of us. "It's alright my love. I'll get new ones."

Pennilyn smiled up at me and gave me another sweet kiss on the cheek, and though I hated to admit it at the time, her kiss couldn't distract from the fact that I was still thinking about that girl in the black dress running away from whatever it was that made her believe she was not welcome in this house.

A/N: And there we have it! The first of many Richard POVs! Hope you all don't mind, but Pennilyn is going to be playing a big role in the first few chapters featuring Richard, because let's face it, they were engaged and were in love for a time.

As for the way updates are going to go down: I really hope I can keep this updated at least once a month, but knowing me, that's probably not going to be the case. So bare with me as I try and carve this story out! I do promise that this story will get finished, because not only do you all want to know what happens, but I want to be able to make it happen as well!

Alright, that is it for now! Hope you enjoyed and I will see you all next time!

XX

Priscilla.