A/N: I appreciate all the reviews last chapter. I love hearing from you guys, so thank you so much!

I don't have much else to say, other than I hope you like this next chapter.

DPOV

I tossed the football to Stefan, "So what's the story with you and Blondie?"

Stefan caught the ball, shaking his head, "nothing. Why?"

"You're such a liar Stefan," I snorted. "You've had a crush on Caroline since you started kindergarten."

"We're friends," he whipped the ball back at me. "That's all."

"Because you're too scared to make a move," I teased him. "Just fucking do it, you pussy. Before she goes to college and has a bigger pool of fish to choose from."

Stefan rolled his eyes ignoring me. He knew I was right. "Like I can take advice from the guy who is in a constant on and off again relationship with Rebekah."

I forced the ball as hard as I could, nearly gutting Stefan in the process as he caught it. "We've been broken up for 2 years, so I don't know what you're talking about."

"Might want to tell that to her," he pointed out. "She has you on a tight leash."

"That's not true."

"Oh yeah?" He raised his eyebrows in question. "How many girlfriends have you had since you broke up?" He threw the ball back at me.

I caught the ball and swallowed as I had no reply that would help me out. "Army life kind of makes that hard," I tried.

"Mhm," Stefan smiled knowing he was right. "So next time you want to call me a pussy for not making a move, why don't you look in the mirror."

"Oh, I know how to make moves," I smirked.

"I was talking about the fact that you're totally whipped."

"How about I whip this ball right at your pretty face?" I threatened.

Stefan just chuckled, before switching the subject. "Speaking of Caroline… She told me you asked her to help give Elena some sort of makeover. What's that all about?"

I shrugged, "Elena has this idea in her head that she's going to reinvent herself before going off to college."

"Why?" Stefan scrunched his eyebrows in confusion.

"She thinks she's going to end up as some lonely cat hoarder," I couldn't help but chuckle at the idea. I could actually picture it. Only I'd still be her friend no matter what she ended up like. Even if I had to maneuver through a sea of cats to get to her couch just to watch Family Feud.

"Where did that come from?" Stefan wondered.

I tossed the ball back at Stefan. Gently this time. "I think I may have made her feel bad by accident," I tightened my jaw just thinking about how stupid my comment was that first night back.

"What'd you do?" Stefan looked at me like I was an asshole. Stefan was pretty close to Elena too. They were in the same grade, and he kept watch over her, after I graduated.

"I told her she didn't know what fun really was like."

"You're a dick," he shook his head.

"I didn't mean it like that," I sighed. "I just wish she would get out more, you know?"

"Yeah," Stefan agreed. "So is the whole reinventing thing working?"

"So far she has the basics," I nodded. "I have to go more in depth… Just wait until you see her though. She looks"-

Just as I was about to explain it, the front door to Elena's house opened up and she stepped out. Stefan's jaw dropped and I followed his gaze. She wore a pale-yellow tank top and high waisted, cut off shorts that were a pale denim color. Her hair was straight today, and she had on make up, and no glasses.

"Holy shit," Stefan said out loud.

Elena walked into our yard oblivious to the fact that Stefan and I stood like two drooling dogs, wordless. "Hey Stefan," Elena greeted.

"Hey," he finally shook out of his hypnosis. "You look great Elena."

"Thanks," she turned to me. "Are you ready?"

"Yeah," I said quickly.

"Bye Stefan," Elena waved with a smile.

"Bye," he waved back.

"Oh!" Elena turned back towards Stefan. "You might want to make a move on Caroline already. She's starting to get annoyed of waiting."

"She said that?" Stefan looked surprised.

"Yes," Elena nodded. "So, quit being a wuss."

I lost control as I threw my head back laughing. Elena had no idea how much that made my day.

"Shut up, Damon," Stefan pouted, before turning to walk in the house.

Elena and I walked to the park that was just about a half mile from our house. I had covered a lot of the basics already with her. Making friends, drinking, parties. But now came the difficult part. And it was only difficult because I knew this would be hard for Elena. She was so shy.

"So, you've done a good job so far taking in everything I've had to say so far," I took a seat on one of the swings. "Are you ready for the next part?"

"I think so," she sat next to me on the open swing.

"Are you sure you're ready to talk about… sex?" I put it boldly.

"Sex?!" She whispered loudly like it was a swear word. "Why not ease me into like, I don't know? Talking to a guy!"

"Right," I studied her closely. "Are you telling me you've never kissed anyone?"

"Who?" She threw her hands in the air. "Who on earth would I have kissed? I've never even talked to a guy that wasn't a family member, besides you and Stefan. Not unless it included group projects in school."

"Ok we'll start there then," I tried calming her down. "Let's start with flirting."

"Flirting?" She seemed calmer now. "How do you do that?"

"It's easy," I casually rested my hands on the chains of the swing. "We do it all the time."

"We do?" She seemed surprised.

"Yeah," I nodded. "It doesn't always mean something."

"Like how? Give me an example."

"OK," I pursed my lips together thinking. "Ok remember when we laid in my bed and I told you, you were like a snuggly teddy bear, and I laid on you?"

Elena shook her head yes.

"That was me flirting with you," I pointed out. "Sometimes it's innocent flirting and sometimes it's intentional."

"What's the difference?" She looked confused.

"It kind of gets a little blurry, honestly," I shrugged. I thought, "Ok say you and I don't know each other, and I started teasing you about something. But I'm not doing it in a way to make you feel bad, but rather in a way to make you laugh. That's a good sign of flirting with intention."

"What's unintentional?"

"That's when you have to read between the lines," I explained. "If I was leaning in closer to you or finding ways to touch you."

"Touch me how?" She looked concerned.

"Like…" I smiled a lightbulb going off in my head. "If I chased you around the playground trying to tickle you."

"Except when I'm in college there won't be"- She froze mid-sentence. "No. Damon no!" She held up a finger, and I wiggled my brows.

Before I could lunge, she had taken off quickly.

I pushed off the swing running after her. She ran around the playground and was just a little faster than her. She ducked underneath the playground to get to the other side faster. I turned around, to meet her on the other side. She screamed laughing. Turning for the slide, trying to run up it, and I caught her ankle, pulling her down, and tickled her mercilessly at the bottom of the slide.

"STOP!" She ordered me.

I let her go, but I remained sitting at the bottom of the slide facing sideways. Her legs were resting across my lap. "That's flirting?" She raised her eyebrows in doubt.

"It's really childish flirting yes," I chuckled.

"But what about real flirting? What can I expect from mature college guys?"

"They probably aren't that mature," I pointed out.

She rolled her eyes, "show me. Pretend I'm a girl you want to make a move on."

It was hard to imagine Elena as a stranger to me. I've known her so long. "Are you new here?"

It took her a second to realize what I was doing. "Um… Yeah," she looked at me suspiciously.

"I thought so," I gave her my famous crooked grin. "I couldn't forget a face like yours."

"Oh, come on," she threw her head back laughing. "That is so cheesy! Please don't tell me those are the pickup lines you use on girls."

"I'm serious," I kept my face as neutral as I could. I moved my hand to her face, rubbing my thumb on her cheek for a second as I kept staring into her eyes. I moved in a little closer, so we were just inches apart. "You're beautiful." I held her gaze, making sure to deeply look into her eyes.

Elena was holding her breath as her face mirrored mine.

My smile slowly crept across my face as I released my hold on her. "And that's how it's done."

"Ugh," She slapped my chest. She stood up and hoped over me. She walked over to the merry go round spinny thing. She stood on it, sitting on one of the handlebars. "So, what about kissing? I mean… I've never like made out with someone before."

I gently spun her around, "You can practice at the party I'm taking you to next weekend. We'll find someone."

"Ew," she grimaced. "I went to high school with everyone there. They're all gross."

"Who cares?" I kept pushing her in circles. "It's not like you have to date them. It's just practice."

"I am not doing that," she crossed her arms.

"Well, it's either that or risk making out with someone you actually like for the first time at college," I shrugged.

She seemed to ponder that idea.

I hoped on the merry go round, standing in front of her. "Ok I know you don't want to talk about sex, but since we're talking about guys and college and parties and drinking…" I leaned on the bar behind me. "Just be careful, ok?"

"I took sex ed Damon," she blushed. "I know all about birth control and condoms. You don't need to lecture me."

"Not that," I looked at her. "Guys can be… assholes," I said bleakly. "There are guys that are really charming and good with their words. But they want you for one thing and one thing only. So just be careful with who you let… you know."

"And I'm all for the women exploring their sexuality thing," I explained. "So, if you want to get your freak on just for the sake of getting it on, then please be my guest. But once it becomes more than that, be really careful. There are a lot of guys out there that just want to get in your pants. And they are really good at making you believe otherwise."

The merry go round came to a stop and Elena stood up walking to stand between my legs. "You're always looking out for me." She gave me a sweet smile before wrapping her arms around my neck and leaning into me.

I wrapped my arms around her lower back, hugging her close. I never remember a hug lasting this long between us. Maybe other than the time I threw sand in her eyes when we were kids and I felt so bad that I waited until she stopped crying before I let go of her.

It felt really good to hold her. And the feeling of it feeling good made me feel uneasy. Was it the fact that Elena had this make over moment that made me realize something different about her? Cause if so… that was really shallow. Or maybe it was the fact that I was finally getting over Rebekah and I realized there were other options out there for me. But I couldn't think of Elena as an option. She was my best friend. Or maybe it was the fact that she was a woman now. She was an adult, who was going off to college. Even though she was only two years younger than me, I always thought of her as a kid. But she wasn't a kid anymore.

She pulled away suddenly a mischievous smile on her lips, "Last one down the slide has to buy ice cream," she said before jumping off the merry go round.

This was something we did all the time as kids. You had to run up the stairs go across the monkey bars, through the tunnel and down the double slide.

I was close on her heels as she ran up the stairs. And when she went across the monkey bars, I swung myself over the top and crawled across the top jumping down in front of her. "That's not fair!" She called out. "That's cheating!"

I ignored her, knowing she was a really sore loser. I slid like a penguin through the tunnel, and she was close behind me. I got to the double slide about to go down when I heard her yelp out in pain loudly. I looked behind me quickly, worried she got hurt.

"Sucker!" She whizzed past me and before I could even think she was sliding down to victory.

"Who's the cheater now?" I shook my head as I slid down to meet her.

"Not my fault, you fell for it," she held her head high like she was so proud of herself. "Now come on… You owe me some ice cream."

A/N: Let me know what you thought! See you next week :)