To say Oliver was surprised to hear from Sara was an understatement. When he first got her message from his EA, he was sure she was mistaken. Sara Lance would not be leaving him a message at work. A voice mail or a text, sure. But not at work. Then he realized it had been years since they had spoken, she probably didn't have another number for him. Last he spoke with her, he was living with his mother and helping out at his friend, Tommy's night club. He was not CEO of QC, he didn't have his own place and he didn't have a cell phone. He debated on calling her back, he feared she was going to tell him she was dying, or some equally bad news. Why else would she be calling him, after all this time? He thought it over for way too long, but in the end he decided that he needed to know why she had reached out now.

Sara always surprised him back when they were close friends. From telling him he was not her type because he has a penis, to turning around and taking care of her sister when she was sick. That had saved her from being stuck on the island with him. That though is another story altogether. So, he called and it seemed she was just as surprising now as she ever was. The first words out of her mouth after the, how are you were exchanged was "I need to know where you hire your dates." he almost choked on his air.
"You what?" Oliver asked
"I need to know what site or whatever, wherever it is you find your dates." Sara answered
"Who said I hire them?" Oliver was sure he had never paid a women to go anywhere with him. He had a long list of women who would go just about anywhere with him.
"I do, I say you hire them. Oliver there is a different girl every weeks. You're not telling me you have multiple girlfriends and they are all ok with this are you? Because if you are I
"No" Oliver interrupted her. "I just have a lot of friends that are willing to go places with me for free."
"Hmmm, ok well do you have a male person who will do you um.. favors for free?" Sara didn't believe him for a second. These girls were escorts, they had to be.
"I don't swing that way Sara, and last I heard neither did you." Oliver knew she was gay. Two reasons, one she didn't hide it at all and two, she told him when he was dating her sister and he tried to hit on her.
"I don't want to have sex with him. I need him for a weekend in Vegas" Sara didn't understand why he was being so difficult.
"You want to take some one to Vegas?" Oliver asked
"Yes" Sara replied, thinking he was finally getting the point
"Ok, you talked me into it, I'll go" Oliver wasn't sure why she didn't just come on out and ask. If she wanted to try and be friends again and go to Vegas, why didn't she just say so? Women, he'd never understand them. That's why he stayed single.
"You?" Sara was confused
"Were you not asking me to Vegas for the weekend?" Oliver was so confused
"No, Sigh" Sara paused, she was making this too hard. This was not her place to tell all of Felicity's business, but at the moment she didn't think she was going to get the information this way, not over the phone, without telling him the whole story. So she decided Felicity would have to meet him and tell him herself.
"Ok, look Oliver, I called you for a friend, in need of an escort. Since you seem to be holding this underground escort business information a secret, it must be for the elite multibillionaires, but she needs the help. Will you meet with her please? Then decide if you will give her the information or not?" Sara waited, hoping he would say something and not hang up on her. It wasn't lost on her that she hadn't talked to him in years and when she called for the first time it was for this. Not to talk or be friends, but because she needed something from him.
"Ok Sara, I'll meet with her" Oliver said after a long pause. "However" he started before she could speak. "However, I make no promises, they may not accept her as a client." He was just plain lying now. But, he wondered about this girl, this friend of Sara's that needed a date for a weekend in Vegas of all places. That had to be the easiest place to get someone to go with you. Why was this girl hiring someone? "When is the trip?"
"Fourth of July weekend." Sara answered
"Almost eight weeks away. Your friend cant find a single date in eight weeks" Oliver was nervous, but still there was a pull to meet this girl.
"Not my story to tell. Just please listen to her." Sara sounded like she was beginning to beg.
"Well, alright. I guess it can't hurt to listen."

The next thing Oliver knew, he had dinner plans at Sara's place on Thursday night. She assured him her friend would be there to explain things to him. In return Oliver was bringing the contact information for the escort service he used, and that was none. He would come clean at dinner. He just needed to meet this girl and figure out what was so wrong with her that she couldn't get a Vegas date. Maybe, she just came on too strong. Or, maybe she was gay like Sara, but not open yet? He didn't know, but he did know he was going to find out on Thursday, and as a bonus he would get to reconnect with Sara. Oliver slightly said prayer to whoever was listening that he would make a connection that night. After being alone (Mostly) for five years on the Island, he thought coming home he would be surrounded by not only people, but friends. He was wrong. Oliver Queen was lonely, surrounded by people all day everyday, yet he only had one person he called a friend. His driver John could always be counted on for a drink after work or to watch a ball game on a Saturday. Even though he was paid to drive him, he wasn't paid to just hang out with him.
This was his chance to reconnect and possibly make a new friend. Oliver was not going to pass up this chance for a little piece of normal in his life.