Multi- Fandom Imagines

(Gilmore Girls) Jess Mariano x Fem! Reader: NYC

Requested for a Jess imagine :-)
Inspired by when Jess asks Rory to run away with him!!!
AuroraManwell

You had dated Jess back in high school and you felt like he was your other half that you were meant to be with.
You were close with Luke too and you both enjoyed joking/snapping at Taylor.
Then one day, Jess left town, you, and Luke.
Now you are exploring the colleges you applied to see where you want to go because pining after a boy who left just won't do.

Jess' POV

I show up at Luke's and I walk in.
He asks "What are you doing here, Jess?"
I answer "Where is Y/N? She's not home!"
He answers "New York City because she wants to go to college, which I wish you would've done! Why? Do you want to break her heart again?"
I knew he would know where she is.
I answer "No. I want to fix it. Do you know exactly where I can find her? I need to ... I need to tell her she was right about me and I was wrong in how I treated her."
He replies "Y/N called and said she was going to Brooklyn Bridge this afternoon and some pizza place for dinner tonight. Don't make me regret telling you about this."
I reply "Okay send me the address for the pizza place because if I miss her at the Brooklyn Bridge, then I need to find her."
He nods and I exclaim "Thanks and uh it was good seeing you, Luke."
He replies "Uh huh you too Jess."
I run out the door.

I crank up my car and start driving.

Y/N's POV

I know people say New York City is not the place to live, but I just have always wanted to.
I have an idea on what I want to do, a little bit of money, and a dream! I feel great about it!

I know one of my friends from my high school band said she would be interested in rooming with me if we are accepted to the same college. I'm personally so excited. I actually did apply to 4 colleges including community colleges.

My mom said it was cool if I went to NYC alone, which is crazy because she is usually uptight about all of this. I personally am shocked, but not going to say anything.

I realize I finally made it to Brooklyn Bridge.
Omg wow this place is beautiful.
Ahhh the view is crazy! I'm in love. Wow!

I stand and lean against the railing.
I then start taking photos.
I hear my name and turn around.
I see Jess Mariano walking towards me.
OMG :-/ :-) :-( what the heck?!?!

When he reaches me, he exclaims "Look I know this is weird that I'm here right now. All I ask is for 5 minutes of your time."
I nod and reply "Go ahead."
Am I too nice? yes :/

He exclaims "When we dated, I was young. It's been two years and I've thought a lot about it. I've thought a lot about you. I ... I can't help but feel I messed everything up by leaving. Am I right?"
I answer "Yes. If we had talked, we could've worked it out."
He shakes his head and says "I think I needed that time away despite that I hurt you. I truly needed to find who I was. I was lost and irresponsible. Now I'm self aware and wanting to fix what I broke. That would be you."
I interrupt him and say "You may have broken me, but I put myself back together. I've been doing good recently. I'm here for college tours actually."
He replies "Yeah Luke told me."
I ask "Wait? Did you keep in touch with him?"
He shakes his head and replies "No I haven't. We may have talked once or twice. I did go today to find you and he said where you would be. Don't be mad at him. I truly wanted to fix things with you."
I ask "And how are you planning to do that?"
He answers "I want to ease back into your life. I have a very small place here like the size of a closet haha. We can occasionally hang out and when you're ready, we can date again if you still want that."
I reply "I'd like that a lot."
He smiles.

I ask "So wanna try some gyro with me? I saw a cool truck and I am hungry."
He laughs and nods.

We walk over and get some.
We each pay for ourselves.

We then sit on a bench and watch as a band plays and kids run around with bubbles.

I exclaim "I'm glad we could reconnect. I always felt like you were my missing piece. I also missed being able to sit in silence with you and just observe people. We did have our fun."
He nods.
I ask "Hey! Wanna come to the pizza place tonight with me?"
He answers "Are you sure? I would say yes, but I don't want to feel like I'm pushing myself back into your life."
I reply "It's pizza not an engagement. Besides, I've applied to colleges already and it's summer. You won't distract me."
He smirks and replies "Since you're sure, yes."
I reply "I can give you my number too. I will also show you book and record stores when we have another day to hangout."
He replies "I'd be honored to see them with you."

THANKS FOR READING!!!!
ILY!!