On the Friday night after Damon and Elena had decided to…"See where things go", Elena sat on the kitchen counter in her pajama pants and t-shirt, swinging her legs, swirling her finger around the orange bowl filled with brownie batter. Jenna had demanded comfort food that night, so they'd settled for takeout soup and microwave brownies. Jeremy sat at the kitchen counter, doodling on his notebook paper. It had been months since he'd actually sketched, but Elena was thrilled to see a pencil in his hand at all.
The doorbell rang and she hopped down, announcing that she would answer it. She opened it and tilted her head to the side. "Hi." She smiled. "We aren't going out like that are we?" Damon asked, eyeing her pajamas. Elena raised an eyebrow. "I wasn't aware we had a date." She admitted, confused as she wracked her brain to see if he'd mentioned anything. "See…I had this whole idea that I was going to surprise you for our first date and it was going to be romantic or whatever and I'm screwing it up." He said, turning to leave. Elena laughed and ran out after him. "Wait, wait!" she said, grabbing his arm. "You aren't screwing it up. I just…didn't know what was going on." She said. "Come back inside. Give me ten minutes." She said, taking his hand and leading him back inside the house.
"Jenna?" Elena called as they stepped inside. Jenna walked through the house, brownie batter smeared across her forehead. "I don't know how to work this stupid oven." She grumbled, and then noticed Elena wasn't alone. "Hello." She said, looking to Elena for explanation. "Jenna, this is Damon." She said, her hand resting on his bicep as she introduced them. "Damon, this is my aunt Jenna." She smiled. "And if it's okay, I'm gonna go hang out with him for a while." Elena smiled. "Damon, why don't you have a seat and we'll be right back." Jenna said, grabbing Elena's hand and dragging her up the stairs. "Why didn't you tell me you were dating someone?!" Jenna whispered and Elena fought the urge to roll her eyes, since she knew Damon could hear them no matter how quietly they talked. "This would be our first official date. We've been hanging out for a while but it just kind of developed into something recently. I didn't know he was coming over. He surprised me." Well, that was a version of the truth, anyway. "So that's who you've been studying with so often. He's really hot!" Jenna laughed. Elena blushed and shuffled her feet. "Oh yeah…studying." "Wait. NO! I'm supposed to be parental. Um…isn't he a little old for you?" she asked. Elena furrowed her eyebrows You have no idea. She thought. "Not really. He's great, you'll really like him." She said, but she knew that probably wasn't the truth. Even on his best day, Damon wasn't exactly parent approved.
After Elena reassured her a few more times, Jenna finally left her alone to change. Elena put on a white sundress that fell right above her knees. She put her hair in a ponytail and touched up her make-up, then grabbed her bag and headed downstairs. "Ready?" she asked, holding out her hand. Damon nodded and stood off the couch. "Wait. I've got this. Don't stay out too late. Call if you need anything." Jenna said in her best chaperone voice. Elena laughed. "I will Aunt Jenna." She promised, linking her fingers through Damon's. He waved goodbye and followed her outside.
When they reached the car, Damon opened the passenger side door for her. "So I'm hot, huh?" he smirked. Elena laughed and smacked his arm lightly. "I knew you were listening! That's just what you needed…an ego boost." She rolled her eyes. Damon caught her off-guard with a kiss. She wrapped her arms around his neck and leaned back against the car. After a moment, they came up for air. "Sorry. I was supposed to do that at the end of the night, wasn't I?" Damon asked and Elena shook her head, resting her hand on his arm. "No. That was perfect." She smiled. She leaned up and kissed his cheek then ducked into the car. "So, where are we going?" she asked. "It's a surprise." He said and then contorted his face as if the sentence had tasted bad coming out. "What's wrong?" Elena asked. "I'm not good at this stuff. All the romantic comedy fairytale crap…that's not me, that's Stefan. This comes natural to him and I have no idea what I'm doing and I just don't want to disappoint you." He rambled. Elena reached across the gear shift and took Damon's hand. "You're better than you think." She said. "And the romantic stuff is nice, don't get me wrong. But I just want you, Damon. Be yourself." She smiled. Damon reached across and kissed her again. "Okay. We should go. Before our entire date consists of making out in your driveway." He laughed, stealing one more kiss before putting the car in gear and pulling out.
Ten minutes later, they were pulling into the woods. "Oh I get it. You brought me here to kill me." She teased him when he opened her dor. Damon rolled his eyes. "You aren't funny. Come on." He motioned for her to get out . Elena returned the eye roll and stepped out. Damon popped the trunk and pulled out a basket, taking her hand and leading her deep into the woods until they came upon the ruins of the old Salvatore Home. "This is where I grew up." He said, motioning around them. Elena knew that..Stefan had brought her here once, but she didn't reveal that. Damon was trying…he was showing her a part of himself he didn't often show anyone. Elena answered him with a smile. "Thank you for bringing me here." They sat down together and Damon began pulling things out of the basket. It was a simple meal, pasta and bread but the fact that he'd cooked for her amazed her.
A few hours later, he pulled back into her driveway. He walked her to the door and then pulled her close. "So not a bad date?" He asked. Elena smiled. "It was an amazing date, Damon. " she promised, wrapping her arms around his neck. "I should probably go before I get on Aunt Jenna's bad list." He pouted. Elena smirked "You know…you could always sneak in later." She teased. "Hmm…we'll see." He teased right back, leaning in for a good-night kiss. "Bye." He whispered. Elena smiled "Bye." She said back, but as she turned her head to watch him leave, her smile faded. "Matt? Hi!" she said, instantly feeling bad. This was awkward. "Umm…this is Damon. Damon, this is my friend, Matt." She said. "Jeremy invited me over." He said, looking between her and Damon. Elena walked back down the stairs, standing beside Damon. "Oh…uh, yeah. He's inside, I think." She said dumbly. "Well, I'm gonna take off." Damon announced, leaning over and catching Elena off-guard with a steamy kiss. Matt turned and walked in the house.
Elena pushed Damon off. "Damon!" she scolded. "What? I'm just kissing my girlfriend goodnight" he said and she could practically see his blood boiling. "You were marking your territory. You might as well have peed on me." She said, walking away. "You think I'm actually worried about the quarterback?" he laughed. "No. I think you're being you. That you are acting out." She said, moving to open the door. Damon's hand came down over her's. "Hey…I'm sorry." He said. "Give me a break. I haven't actually dated anyone since the 1800's. I'm a bit out of practice. I could tell there was something there and…I just wanted to make sure he knew you were spoken for." He said, pulling her into his arms and pouting at her. "Well, I think he got that loud and clear." Elena said, stubbornly. "Come on…don't be mad…" he pleaded. Elena rolled her eyes. "Fine." She said. "But from now on, you're nice to Matt, got it?" she asked. Damon nodded. "Of course. I'll talk to you later, okay?" he asked. Elena nodded and he leaned down and gave her a soft kiss.
Damon's POV
Damon drove home in silence. He parked and walked inside, greeting his brother before heading up to his room. He unbuttoned his shirt and tossed it in the laundry basket then moved to his pants. "Whoa. Not even a hello first?" he heard from the bed. He spun around to face her. "Katherine?"