"Okay Damon, if we are going to do this then we have to do it right" Elena said as seriously as she could manage.

"Yeah, yeah. Honesty and all that crapola. I get it Elena okay? Let's get to the juicy stuff already" Damon said impatiently, his trademark smirk never wavering.

Elena had been devastated when Stephan had up and left her four months earlier. Damon said the only excuse he gave was how he never wanted to hurt her again. Stephan and Elena had a lot trouble getting their relationship back to normal after his last run in with human blood. Nothing felt right and normal for them anymore and Stephan sent everyday living with the guilt of knowing he actually hurt her that time. He knew if it happened again then she might be hurt worse or even killed next time so he left. Elena spent a month and a half mopping around her house. Finally, she had the overwhelming urge to have fun. She knew exactly who to go to if she wanted to have real fun so her and Damon had been spending their lazy summer days together.

On this particular day, Elena brought a toy over that Bonnie had bewitched for her. This toy doubled as a lie detector. If the flashlight turned on after a statement, it meant that person was lying. Elena and Damon decided to play their own truth game in the form of 20 questions.

"So, we are gonna play twenty questions with the flashlight, it will tell me when your lying, and Bonnie told me the light will stay on if you try to lie your way through to a somewhat truthful answer. Meaning, it detects the truth of the entire statement" Elena explained.

"And no questions are off limits, right?"Damon asked while wiggling his eyebrows, causing Elena to giggle.

"At this point Damon, you already know too much about me. Why stop now? I will answer any question you throw at me" Elena challenged.

"Okay, so I think I should go first. Me being the crafty, evil one and all. What to ask? Oh what to ask?" Damon contemplated causing Elena to regret saying she would answer anything.

"I'll start off tame"

"Oh well that's new, I didn't know you could be tame" Elena said mockingly shocked.

"Well there goes that, okay you asked for brutal. How many people have you had sex with?" Damon spit out while Elena rolled her eyes.

"Oh well that's easy. Two. I have had sex with two people. Matt was first and then Stephan. I won't return that question considering I'm sure you couldn't tell me" Elena said, feeling relieved that that was what he considered brutal. The flashlight never even flickered. Damon was kind of relieved she had given such a tame number, knowing full well how right she was about his own number.

"So I pretty much just wasted a question. Anyways, your turn Elena. Lets make it good" Damon said mischievously.

"Umm, I know, what was your favorite decade and why?" Elena had always wanted to ask about his time between 1864 and now. Stephan never really liked to talk about exactly how old he was, he felt it put us on different levels so it was always fun to ask Damon all about his life.

Damon thought about it for a few minutes before saying "It's probably a tie between the '60's and the '70's. The '60's were great because of the feeling of liberation that came with the music and the free feeling that came with the hippie movement and Woodstock and all that. I mean the Beatles, The Doors, Jimi Hendrix and everything else musically was freaking brilliant. Then the '70's was torn between Disco and classic rock. It was all awesome. Except for the wars and stuff but being a vampire kinda gave me a free pass through all that stuff".

Damon looked up to see Elena rolling around on the floor laughing. He had been so wrapped up in his memories that he hadn't noticed her hysterical laughter. "What's so funny?"

Elena caught her breath long enough to explain "I just got this visual of you dresses up in the whole hippie get up, with the peace signs and everything. I have to say it is hysterical. Please tell me you have pictures."

Damon lightly chuckled to himself "none that you will ever see" he said seriously, watching her face turn into a pout. "Okay moving on, my turn. Oh I've got it. Wow, I am evil. Have you ever had an orgasm and if so what was the biggest turn on about the whole experience?"

Elena's face immediately turned red. She started to say "My first orgasm…"but the flashlight turned on and Damon looked at her in shock. "You've had sex with two different guys, and you've never had an orgasm" Damon said, shocked to his core. "Oh you poor thing, that just sucks. Boy do I feel sorry for my brother the next time I see him" he said, mostly to himself. A look of pure mortification passed across her face, "oh please don't say anything Damon, that would be so embarrassing" Elena said pleadingly. "I think we need some drinks" Damon said to try and lighten the mood. Elena immediately started nodding her head in agreement. Damon poured two glasses of scotch and grabbed the bottle in the other hand. He handed Elena the glass and watched as she pounded down the liquid.

Shocked Damon asked "Damn, where did you learn to chug like that?". Elena giggled and said "that counts as a question. That means I get two next round." Damon rolled his eyes in response and looked at her expectantly for the answer to his question. "I was a partyer before my parents died. I was actually at a party the night they died. They had to come pick me up at some random house in the middle of nowhere and we were in an accident on the way home. Thanks to Stephan, I lived and they didn't."

Damon spent a second speechless "Elena, I'm sorry. I had no idea."

"Oh no Damon, it's okay. You didn't know. Doesn't make it any less real. Might as well talk about it" she said, brushing it off. "So where do we stand?" Elena asked, desperate for a subject change. Damon was momentarily surprised by her question until he realized she was referring to the game. "Oh I have 17 questions left and you have 19 left. I think I've gotten a little carried away with this game. You ask two so we can even it out." Elena nodded in agreement and thought long a hard about her questions.

A.N. okay it's 4:21 in the morning right now and I really need some sleep, so let me know what you think. I randomly came up with this idea and I love it but you guys might think it's boring. Let me know. I love reviews. We have tons of questions coming up so send me some suggestions if you have any. Thanks. Ashley