How He Confesses/First Date - Oliver Queen

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A/N: This scenario is kind of intermixed with the next scenario with your first date with the heroes. This is just a heads up because you will not see him in the next set of scenario for the First Date.


Every time you met up with Oliver it was always the same:

"(Y/N), will you go out with me?" "No." "But-" "No."

Sometimes he would look you dead in the eye with a serious expression and ask you the same question. At times like that, it makes you want to say yes but there are so many other thoughts running through your head about him. It was no secret that the famous Oliver Queen was a player and you could simply become just another one of his conquests and you didn't want that. No. You want to have something more serious than just a casual fling.

Maybe you should give him a chance....people can change....can't they?

After a month of the man asking you finally gave up and said 'depending on how he acts on this 'date' then you will agree to go out with him in the future.' The reason behind saying that was more complicated than Oliver realized as you were going to use this opportunity to see how he will act around you and if his intentions are true.

A week on Friday Oliver turned up at your doorstep at 6:00 pm and lead you to a extravagant limousine. The limousine took you through the richer part of Starling City and parked outside of a fancy restaurant with an impossible to say name. You walked in with Queen at your side and the whole place was pack with some of the richest people in the city. You began to feel small as the feeling of being watched by each and everyone of them creeped up your back, the feeling went away when the waiter took you both to the back of the restaurant where it was more private.

"Order anything you want, no matter how expensive I'll pay." he said with a grin.

You simply just rolled your eyes and ordered the cheapest thing on the menu but it was still your favorite (F/F). His smile dropped slightly as he realized that he wouldn't be able to try and win you over with his money. The waitress took your order and the conversation between you both flowed smoothly as if it was just another of your random encounters. Once the meal had finished, you got into the same limo as before and were headed towards the carnival near the beach.

And this is everything started to go down hill. You tried to pay your own way into the carnival but Oliver beat you to it and got both tickets. There was still time before the the actual event started and there were stalls full of games covering the area around the main tent. You decided to look at the different stalls and try to win a few prizes. This where it got annoying. Every game you wanted to play, Oliver jumped instead to try and win the prize. When you wanted to pay for some snack, Oliver jumps in again and paid for you.

It was becoming overwhelming. By the last stall you had enough and headed towards the entrance to leave. 

"(Y/N)! Where are you going? The show hasn't started yet." 

"Oliver I know you have the best intentions but it's too much. I can do things on my own like throw a ball at a few damn tins and I can pay my own way in." You answered back leaving the carnival with Oliver close at your heals.

"I'm sorry (Y/N), I didn't know. I'm used to this, I'm used to paying for my date but I didn't take into account that you are different. Tell me what you want to do and I will do it."

Stopping, you thought for a bit before taking his hand and dragging him to a nearby park. You took him to the highest hill and sat down. Within five minutes the sky began to light up, the firework display had started. You watched in wonder as the lights exploded above your head and you relaxed enough to lay your head on Oliver's shoulder. You missed the smile that grace his lips as you did so and he put an arm around your shoulder.

"This is definitely better than what I had planned. It's very peaceful and nice, thank you (Y/N). I just have to ask if you would give me another chance to take you out again."

You just laughed and replied with,

"Of course you idiot, this can counts as our first date though."

It may not have started off great but you both had a great time in the end.


A/N: I know you are probably sick of seeing these author notes by me but this needs to be said. Remember when I said I would be setting a deadline for the scenarios, well that starts after the next two scenarios. Plus this may change cause I am trying to find an apprenticeship or a job, I need to earn a living somehow.

These are the update dates, if I don't update shout and scream at me please;

Wednesday: first lot of scenarios - Saturday: The rest of the scenarios that I couldn't finish on Wednesday.

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