A/N: Hey guys. I started rewatching Season 2&3 of Gilmore Girls and kind of got inspired to do a story for Vampire Diaries loosely based on some of the episodes. I have somewhat of an idea of where I want this to go, but we'll see where the characters take me! I'm coming up on the end of my semester and my final exams, so I'm going to try and update as much as possible but it'll be a little difficult. Thanks so much to everyone who's reading and favoriting this, it means a lot. And please review! I'd love to hear what you guys think!

And no. I don't own the Vampire Diaries, Gilmore Girls, or any affiliated characters.

"So please explain this to me again?"

It was Saturday afternoon, and Elena was lying on her bed, deep in conversation with her boyfriend. She sighed. "Look Stefan, I know you don't understand but with Jenna and Alaric gone on a teacher's conference and Jeremy spending the day with Bonnie, I don't know. I kind of wanted to spend the day by myself. Maybe watch a bunch of movies, write in my diary, paint my nails, and just sort of relax and forget about all the supernatural for a while." She got up and started pacing around her room as sunlight streamed through the window and warmed her skin.

"I get it, Elena, I do. I was just really looking forward to spending time with you."

"I promise tomorrow is your day, from morning to night. You can plan it, or I will, or we can even hire a professional to do it. Whatever you want."

"Alright," Stefan said, laughing. "It's a deal. Have a nice, relaxing day. I love you."

"Love you, too," she smiled and hung up, sitting on her bed again. She picked up her diary and opened to where she left off.

Elena had just sat down on the couch to watch a movie when she heard the door open and slam closed, Jeremy storming past her into the kitchen. "Jer?" she asked. "What's wrong?" She got up to follow him, her movie night temporarily put on hold as concern for her brother overtook her.

"Your best friend's a bitch, that's what's wrong!" he shouted angrily. "She just…uh!" He poured himself a glass of water only to slam it down, causing water to splash on the counter.

Worried and confused, she wondered what could have possibly happened between Bonnie and her brother to cause him to be so upset. She furrowed her brow and looked at his clearly agitated form. "Do you wanna talk about it?"

He sighed, staring absently out the window. "No, not right now." Turning back to look at her standing in her pajamas with movies, nail polish, and magazines spread out all over the living room, he smiled. "This was your big plan for the night? A pajama party for one?"

"Hey! Shut up!"

"Whatever, I'll be in my room," he laughed, heading up the stairs.

Elena was about halfway through A Walk to Remember, sobbing at Mandy Moore's tearful confession of leukemia to Shane West, when the doorbell rang. She knew she had gone through an internal debate on whether or not to call for a pizza, but she was pretty sure she had decided to wait to order until after the movie was over. Wiping at her eyes haphazardly, she opened the door only to step back in surprise.

"Damon, what are you doing here?"

He was standing on her front porch, wearing his signature darkwash jeans and black v-neck, holding a bag of what appeared to be takeout from the Grill. "Food delivery," he smirked as his eyes wandered up and down her lean frame.

Fidgeting, she was suddenly very aware of how she must look, wearing only short pajama shorts and a tank top, with messy hair and puffy eyes. "Umm…"

"I was chatting with Ric earlier, and he mentioned that you happened to be all by your lonesome today," he cut her off. "He said he and Jenna would feel better if I could swing by. And I'm glad I did," he said stepping inside and looking around the scattered living room. "This looks like a scene from a bad chick flick. Did you and Stefan break up or something?"

"No, I was just taking a personal day. Does no one get that?" she scowled, closing the door behind him. Taking a deep breath, she relaxed. "Thank you for the food, Damon. You can stay and eat if you want," she offered, leading him into the kitchen.

"Who am I to pass up dinner with a beautiful woman?" His voice melted over her, causing heat to rise in her chest.

"Elena, who was at the door?" Jeremy asked, appearing at the bottom of the stairs. "Damon, thank God you're here," he exclaimed, spotting the two of them.

They both turned to him, shocked. "Did you just say what I think you just said?"

"Thanks, Elena. Really," Damon snarked, setting the food on the counter. "Is there something I can do for you, Gilbert?"

Jeremy hesitated, glancing at Elena. "Actually I got in a fight with Bonnie today, and I, well, I kinda wanted some advice."

"You realize me and Judgy hate each other," he deadpanned.

"Can you pretend you don't for five minutes?"

Damon sighed, exaggeratedly. "Fine, I just hope I don't overexert myself."

As the boys walked into the living room, she started to take the food out of the bag and put it onto plates, a feeble attempt she and Jenna often used to hide their nonexistent cooking skills. She shook her head. Sometimes Damon and Jeremy's friendship (if you could call it that) baffled her. Logically she would have thought that, out of the two Salvatore brothers, Jeremy would be closer to her boyfriend. Especially considering the fact that Damon once killed him. However, the two seemed to find common ground on a lot of things. Both had been incredibly unlucky with love in the past, dealing with feelings of loss and rejection. Oddly enough, she thought that Jeremy looked up to him in a way.

"Look Jeremy, girls like Bonnie are really independent and don't like having their ideas and opinions undermined. Don't tell her she's wrong; just listen to her. Even though you sure as hell know that whatever she wants to do is insane and careless."

Elena cocked her head to the side, picking up pieces of their conversation. What did Bonnie do that Jeremy didn't agree with? Was it dangerous?

"We're still talking about Bonnie, right?"

"What else would we be talking about?" Damon snapped.

"Well, you keep glancing at the kitchen, and I know you're worried about Elena's recent suicidal tendencies."

Elena shot her head down at hearing that. She always knew that Damon found that whole situation frustrating and irritating. But he had been worried about her. He cared about her. She supposed she really shouldn't be surprised. There had been a myriad of hints pointing to just that; slight indications she just so willingly chose to ignore for her and Stefan's sake. Because he's in love with you. She shivered. Truthfully, she'd been perfectly happy to pretend like Damon's feelings toward her didn't exist, because if she did, then she'd have to consider how she felt about him. That was definitely something she didn't want to think about. She sighed, sitting down at the counter.

"You know it's still take out, whether it's on plates or not."

She looked up as Damon and Jeremy reentered the kitchen. "Damn, Damon. You got enough food for like ten people."

"I've seen you Gilberts eat," he raised his eyebrows challengingly.

"Okay, six people then," Jeremy relented. Turning to Elena, he smiled. "I'm gonna go and try to fix things with Bonnie. Leave me some leftovers."

As Jeremy left out the back door, Damon sat down across from her at the counter. "You know you're good with him," she said absentmindedly as they began to eat.

"Yeah, okay," he rolled his eyes.

"No, I'm serious. I think you guys are, dare I say it, friendly," she teased.

"The kid's not half bad," he gave in. "What are you doing?"

She was simultaneously pouring salt and pepper into a small pile. "Salt and pepper dip. It's the only way to eat a fry."

He raised his eyes brows at her in disbelief. "That looks disgusting."

"Try it. It's a fast food gospel."

He eyed her suspiciously, but dipped a french fry into the condiment mix and stuck it in his mouth. "That's pretty good. Really good, actually," he nodded his head in approval.

"Didn't I tell you? After some 170 years, I'm surprised you've never heard of it before."

The fell into a companionable silence, eating their burgers and fries. She hadn't realized how hungry she was. Thank God Alaric asked Damon to bring over takeout. That reminded her… Reaching into her pocket to get her phone, she remembered she left it on her dresser upstairs.

"Damon, can I borrow your phone to call Ric? I wanted to thank him and Jenna for asking you to feed me," she smiled.

"Umm, no," he deadpanned.

"What? Why not?" she asked, taken aback.

"We don't want to interrupt them on their weekend away, Elena. You never know what they could be doing," he said suggestively, doing that eye thing he always does.

"Ew! That's my aunt and my history teacher, Damon! Nightmares!"

"Oh, Elena. It's the birds and the bees. Everybody does it…"

She crossed her arms and glared at him. "Stop changing the subject. Why can't I just call them and say thank you?"

"Can you just let it go?" he said exasperatedly, starting to fidget slightly.

"Wait a minute, you're squirming!" she giggled.

"Elena…"

"I've never seen you squirm. It's entertaining."

"Look, it might not have technically been Ric and Jenna's suggestion that I swing by," he alluded.

"You wanted to come over," she grinned.

"I was just out of bourbon and Stefan was being depressing, and I just thought you'd be more fun," he confessed, giving her a soft smile.

She sat there and thought about his words, finishing up her food. After a second, she looked back up to him. "You didn't have to lie about it. You know you can always come over," she returned his smile. She got up and began piling their plates next to the sink to be washed later.

Damon's eyes wandered and soon fell on the TV, which still had the DVD player on pause. "Did you want to finish that?"

Turning to following his gaze, her brow furrowed. "I thought you hated chick flicks?"

"Maybe, but l do love Mandy Moore," he smirked at her mischievously.

By the time the movie ended, she was lying across the couch, one arm on her stomach and the other behind her head with her legs strewn over Damon's lap. As the credits started to roll, his feet were propped up on the coffee table while his fingers were slowly rubbing circles over her calves. "Elena?" he leaned over her, brushing a stray piece of hair behind her ear. "Elena?" he repeated, softly.

"Hmm?" she murmured, her eyes heavy in a semi sleep state.

"Why don't I go, and you can get some sleep. You look exhausted."

"Alright," she agreed, as Damon picked up her legs from his lap and swung them around so her feet touched the floor.

They both stood up, Elena leading him towards the front door. "I hope I didn't intrude too much on your night," he said teasingly, trying to lighten the mood.

"I'm glad you came, Damon," she admitted, opening the door. Although she had her heart set on a relaxing day by herself just that morning, she had really enjoyed her evening. Actually, thinking to herself, she always ends up having a good time when she's with Damon.

Noticing he had stopped in the doorway, Elena stepped forward to look outside.

"Stefan."

She looked at her boyfriend coming up the front porch in confusion. He was looking in between her and his brother, his forehead creasing in suspicion.

"Damon…?"

She awkwardly crossed her arms under his scrutiny, aware of how this must look to her boyfriend: her in mildly revealing pajamas and both of them with slightly wrinkled clothes and hair from lying on the couch a little too long.

"Hey, brother. Fancy meeting you here," Damon smirked, watching Stefan's face turn from suspicion to anger. He raised his hands in mock surrender at Stefan's approaching figure, "Hey, I was just leaving. Let's not get all West Side Story here. Besides, we both know how that would end anyway."

"Goodbye, Damon," she hissed, her eyes blazed in irritation.

"Until next time, Elena," he bowed his head, kissing her hand and sending fire up her arm, only furthering her anger at the situation. Straightening up, he sent her a final look and sped off.

"So. Stefan. What are you doing here?" she asked weakly, as he stormed passed her into the house.

"What am I doing here? Honestly, Elena?" he cocked his head doubtfully at her. He looked around the house, taking in the dirty dishes next to the sink and the empty movie box on the coffee table with the credits still rolling on the TV. "I came here because I wanted to persuade you to go out for ice cream with me. I called you, but you were apparently too busy to answer," he narrowed his eyes at her.

"Stefan, you know that's not true! I just left my phone upstairs!" she cried. "Stop making accusations!"

"Elena, I'm sorry, but you tell me specifically you want to be alone tonight, and then I show up and you're with my brother having a cozy night watching movies!" he yelled, pacing back and forth on the wood flooring.

"Look, Damon only came over to bring over some food because Ric called and asked him to check on me," she said, trying to appease him, but the lie tasted somehow bitter in her mouth. "I was already watching something so we just finished it, okay? I didn't plan this."

His face softened, his shoulders slumping as he turned to her and rested his hands on her shoulders. "Why didn't you call me?"

Her face tensed up. "I didn't really feel the need to run and call you the second Damon came over. You know we're friends, Stefan. I didn't think I needed your permission to spend time with him," she said tersely. He took a step back from her, brow one again furrowing.

"You don't, Elena. I just thought that you wanted to spend tonight alone, and if things changed, you would call me so we could do something."

"I did want to be by myself, but he came over, and I wasn't going to kick him out just so I could call you over. I mean, we're spending all of tomorrow together. Right?" she asked challengingly.

"Right," he sighed, exasperated. "You look tired; I'll just see you in the morning." He kissed her temple and swiftly walked out the door, leaving her alone in her front room. She let out a deep breath and looked around the room, decided to just leave it to clean up in the morning.

"Okay…" she muttered, wondering how the hell her night got so turned around. Walking upstairs, she tried to clear her mind of all her racing thoughts, but she still ended up coming back to the memory of Damon's light kiss on her hand, still feeling the electricity coursing through her body.