After Founder's Day, Damon wanted a date with Elena. Just a simple date that would lead to him asking Elena to be his girlfriend. He knew she would say yes, but he wanted to ask her, as she was a sucker for romantic gestures.
Sitting in his bed, he messaged Elena.
Damon: Hey Elena. Do you want to go on a date with me tonight at the Grill? I can get the whole place to myself.
Elena: Sounds lovely. What shall I wear?
Damon: Dress casually. You look beautiful in anything.
Elena: What time?
Damon: 7 pm, but I'll pick you up.
Elena: See you then.
Damon smiled. He had the whole day to come up with the perfect date that he knew Elena would love. He was surprised that Stefan never did this.
Elena, on the other hand, was with Caroline.
"So, you're telling me that you and Stefan broke up?" Caroline was shocked by this reveal.
"Yep. Damon is taking me on a date tonight." Elena smiled.
"WHAT?! Damon Salvatore is taking you on a date?!" Caroline freaked out.
"Yes, Caroline. Damon is taking me on a date. You have a problem with that?" Elena asked, confused.
"No problems. I was just shocked considering you and Damon have been frenemies since you two met. I mean, you always used to hate him. What changed?" Caroline asked, interested in her response.
"I've gotten to know him over time and I found out that he was in love with me." Elena sighed, thinking of how sweet Damon had been.
"So, have you got any idea about what he's planning tonight?" Caroline asked.
"Nope. He said to dress casually, before complimenting me." Elena showed Caroline her texts with Damon, Caroline's eyes widening.
"Wow. He totally has the hots for you! But, you're not dressing too casually, as it's a date." Caroline stood up, going to her closet. Throwing a pair of her nice jeans onto the bed, she moved onto her tops, finding a nice lavender shirt to go with the jeans she had thrown on the bed.
"Caroline, I have my own clothes." Elena smiled.
"I know, but mine are nicer." She smiled, continuing to find more parts of the outfit.
After hours of waiting, Elena and Caroline heard the doorbell ring, causing Caroline to freak.
"He's here!" Caroline smiled as she walked downstairs, opening the front door.
"She's right here." Caroline moved to show Elena.
Elena and Damon looked at each other up and down. Elena had the nicest pair of jeans on, a lavender shirt and a black denim jacket. Damon wore black jeans, a nice black shirt, the top two buttons undone.
"She better be home by 10. I'm joking!" Caroline smiled as she let Elena and Damon head outside.
Arriving at the Grill, Damon opened the door, revealing that the entire place was empty, except a cook and someone at the bar. Fairy lights had been hung from the ceiling, two tables had been put together, and set up for a date.
"Wow, Damon. This is amazing." Elena smiled, hugging him.
"You deserve amazing." Damon smiled back, kissing her forehead.
For the entirety of the evening, Elena and Damon enjoyed each other's company. Damon admired how much Elena loved the people around her and Elena admired how much Damon was willing to do to protect the people he cared about.
Of course, a game of pool was played, Elena barely winning while Damon admired her.
"You win." He smiled, holding a glass of whiskey in his hand.
"Did you let me win?" Elena playfully hit him.
"No. I swear I didn't. I just...really suck at pool." Damon admitted, putting his pool cue down.
"Well, whether you did or didn't, thank you. Thank you for playing with me." Elena smiled, kissing Damon.
"Elena, can I ask you an important question?" Damon sat Elena down, Elena confused.
"Will you be my girlfriend?" Damon asked, earning a passionate kiss from Elena.
"Yes." She smiled, hugging her new boyfriend.
"I love you, Elena." He whispered in her ear.
"I love you too, Damon." Elena had never said those words in that order and before today, she would have never said those words in that order. Yet, saying them now, after everything that's happened, Elena felt happy saying those words.