A/N: Hi, I am back! All of you probably remember me from Sparked Interests. Here I am with another Damon/Jeremy fic and it's inspired by my current obsession with Mad Men. This story is inspired by an episode in S2 where Don tells Joan to find him another secretary.. one that can effectively manage his life and reputation. They didn't really expand on that much.. so I took the idea and this happened. This fic does not take place in the 60's like Mad Men does. There will be no Mad Men characters making an appearance as this is not a cross over. This is modern and is slash so if you haven't read by me before a lot of my TVD work is slash meaning male/male pairings. There may be a bit of het in this though so be warned about that. Updates are most likely going to be slow.. I have a job and graduate college in a few months so this is a busy time for me. But this story needed to be written and I hope you all will enjoy it! Feedback will be greatly appreciated. Also, Damon's character in this story will be highly similar to Don Draper. My obsession with Don Draper is partly what spurred this on. The TVD characters will be similar to how they are on the show but some of them may be different like Elena and Matt for example.

Disclaimer: I do not own The Vampire Diaries or Mad Men.

The agency of Betancourt and Sherman is the top advertising firm in Richmond, Virginia. Jeremy Gilbert is a recent graduate of UVA with a degree in marketing. Fresh out of college with no internship or experience makes finding a decent job challenging. He committed to leaving his retail job so he had to make it work. He applied for entry level positions hoping to get a bite from an employer so he could move to his own place away from the small town and his overbearing sister. Their parents passed away when they were young and his sister, Elena, took custody of him. He didn't get the typical college experience of living on campus and had to commute to his classes. Needles to say, he wanted to land a great job and start making his own way in the world.

Which was why he was so surprised when there was a job posting for a secretary to the creative director of the Betancourt Sherman agency. The posting called for someone able to mingle in all types of social situations, deal with the clients, handle the schedule and anticipate the needs of his boss. Granted, it sounded like a female position, but this wasn't the fifties anymore. The position could turn into an actual advertising position if he played his cards right. He immediately sent off his resume and cover letter, filled with hope. Next, he pulled open Google and searched for information about the agency's staff. The creative director, Damon Salvatore, was 35 years old with a degree from Stanford and an eye for advertising. He came to Virginia from an agency in Los Angeles who merged with Betancourt and Sherman. The article wasn't what had Jeremy in shock.

It was the business picture included. The man was a sight for sore eyes and had the bluest eyes and blackest hair he had ever seen. Not to mention his face was one created by God himself. The way he was posed in the picture sent off an air of total control and confidence. Jeremy knew he had to do everything in his power to get this job. If not no other reason than to stare at that gorgeous face every day. Coming out had never been an option for him. His sister, Elena, was a debutante which meant how he lived reflected on her and her standing within the community. He dated one of her friends, Bonnie, but it became too difficult to keep up the ruse and physically please her. Therefore he had to end the relationship and blamed his career for the break up.

Elena wasn't too thrilled that she had a broken hearted best friend to console. But, she understood his reasoning. He was ready to get out from underneath his sister and her expectations. She'd be fine without him since she had her boyfriend, Matthew Donovan, the son of a stock broker. Matt could be pretentious at times, but there was no doubt he loved Elena and could take care of her. He wanted to be there for her. It was hard to when he couldn't sort himself out. Right then, he promised himself that he would come back to take care of her when he finished his self discovery. He closed his lap top and rose from his chair, going to his closet to change into workout clothes to hit the gym. While he shed his sweater, his phone started blaring music. He ran to his desk and answered it.

"Hello?"

"I'm looking to speak with a Jeremy Gilbert."

"This is him."

"Mr. Gilbert, this is Hilary Joyner from Betancourt and Sherman. Are you available to come in for an interview next week?" asked the professional sounding woman.

Jeremy almost dropped his phone in shock. They were quick in getting back with him. "Yes ma'am. When do I need to come in?"

"How's Tuesday at one o'clock?"

"Sounds great."

"When you arrive, come to the fourth floor and you'll see my desk when you first walk in and I'll escort you to Mr. Salvatore's office for the interview."

"Yes ma'am, thank you," replied Jeremy, hanging up.

His heart started racing and he had no idea how he'd make it through an interview with Mr. Sexy Salvatore.