A/N These wonderful characters are not mine.

This is just a short shot of what might have been if Jess and Rory hadn't been so stubborn in the beginning of season 3.

All conversations in italics are from the show.

Washington Squared

J: I'm sorry, did I hear from you at all this summer? Did I just happen to miss the thousands of phone calls you made to me, or did the postman happen to lose all those letters you wrote to me? You kiss me, you tell me not to say anything. . .very flattering, by the way. You go off to Washington. . . then nothing. Then you come back here all put out because I didn't just sit around and wait for you like Dean would've done? And yeah, what about Dean? Are you still with him? 'Cause last time I checked, you were, and I haven't heard anything to the contrary. Plus, the two of you walking around the other day like some damn Andy Hardy movie. Seemed to me like you're still pretty together. I half expected you to break into a barn and put on a show.

R: When did you see me with Dean?

J: At that stupid summer insanity plea the town put on.

R: Oh, I'm surprised you could see anything with Shane's head plastered to your face.

J: You didn't answer me.

R: About what?

J: Did you call me at all?

R: No.

J: Write me a letter?

R: No.

Rory stumbled over the word, blushing as she changed her mind and her answer, "I mean yes. I mean not really. Yes. I did. I wrote you a letter."

Jess paused mid rant, still carrying the barbs of the argument in his next words when they finally came out.

"Must've got lost in the post." He looked her straight in the eyes, challenging her, wanting it to be true but not sure what to believe anymore.

Rory looked away for a moment before returning her eyes to his scrupulous gaze.

"I never sent it," she confessed, her voice barely above a whisper in stark contrast to the shouting match they'd been partaking in just moments before.

Jess shrugged his shoulders, shaking his head slightly unable to decide which question to ask her next.

He eventually settled on "but you're still with Dean?"

Rory glanced around the store, suddenly very aware of how public this conversation was. Despite the late hour and few customers, she'd lived in this town long enough to know how fast gossip could travel.

"Can we go for a walk? Just to talk. I can't promise to explain everything because quite frankly I'm a little confused and overwhelmed myself right now but I will try my best."

Jess couldn't refuse her when he saw the pleading look in her eyes.

"Okay," he agreed.

They left their items on the counter and headed for the door.

"Rory? Did you forget your purse?" Lorelai asked in confusion noticing the absence of bags in her daughter's hands. "Don't tell me they sold out of mac and cheese? Chocolate? Surely there was at least cho...Oh." Lorelai stopped mid word as she saw Jess exit Doose's behind her.

"Um, mom, is it okay if I just see you at home?" sending a silent signal to her not to make a scene Rory held her breath waiting for Lorelai's response.

"I guess," Lorelai replied reluctantly. She didn't trust Jess and now that she knew for sure what she'd been concerned about for the last few months she trusted him even less.

"Thanks mom, I won't be long," Rory assured her but Lorelai wasn't convinced.

Lorelai waved them off and stepped inside Doose's, noticing Rory's abandoned basket she picked it up, added a few extra sugar laden items and went to pay. Through the front window she could faintly see Rory and Jess heading toward the gazebo. Better there than the bridge, she thought to herself. More eyes on them in the centre of town. Putting the grocery bag in the empty passenger seat she buckled her seatbelt, started the engine and turned the Jeep toward home trying not to think about how much Jess reminded her of a boy she knew when she was Rory's age.

Neither Rory nor Jess had spoken a word and were now standing on opposite sides of the gazebo, each apparently studying their own shoelaces.

"So, this is a little awkward huh?" Jess looked up at the sound of Rory's voice. The hostile tones from earlier had dissipated and the carefree girl who had found him in Washington Square Park 3 months ago was suddenly before him again.

"You wanted to talk, the floor's all yours," Jess gestured at the boards beneath their feet, his tone slightly mocking.

"Okay. Well, I guess I could just give you this," Rory pulled a worn wad of folded paper from her purse and held it out to him. "There's your letter."

Jess took a step closer to Rory and reached the remainder of the distance to take the paper from her hand. She held it tightly for a few seconds before releasing her grip on it, letting out a heavy sigh as he turned it over in his hand.

"So, I'd better go. Mom. Food. Movie." Rory began to back away, preparing herself to bolt but regretfully ruling that option out on account of her Friday night shoes. "It's all in the letter Jess."

Jess was still standing looking at the note in his hand like he was trying to read the words without opening it.

"I guess I'll see you around." Rory felt sick to the stomach seeing her heartfelt words so close to being read, her true feelings so close to being discovered. Forgetting her concern over her shoes she fled the scene, unable to erase the indistinguishable look in Jess's eyes from her mind.

Jess watched Rory run away from him again for the second time in recent months. He lit a cigarette, puffing the smoke into the night air, as he walked toward the bridge, curious to find out if he was holding the fate of Rory's heart in his hand or his own.