Prompt (by ladybuglloyd on Tumblr): Oliver has to buy Felicity something for a mission because she doesn't have time but he has no idea what she likes. He ends up buying the wrong thing or has an uncomfortable time shopping in a women's store.
A/N: I didn't completely follow the prompt, but this just escaped from me. I do plan to write another one shot which does follow the prompt more, so be on the lookout for that! For now, enjoy this one Also, please leave a review of some kind, because I'd love to know what I could improve on my writing. Also, the link to Felicity's dress can be found on my profile :)
A Tale of Stores and Shopping
When Oliver invited Felicity to come along to a charity gala he had to attend, he hadn't expected this to happen. He had expected her to freak out when he specified it wasn't as his EA, but as his 'date' date, and that did happen. But when she told him that she didn't have time to shop, and that he would have to buy something for her to wear, he was the one to freak out. Which was unsurprising to say the least. He didn't have any idea what to shop for a woman! What she needed, or what she wanted, or what colour she wanted... He had no idea at all. Normally he'd go to Thea for advice, but she was so busy with Verdant that she wasn't able to help him.
That's how he ended up here, in a dress shop, with no idea what to buy. He had a general idea of the colour (green, because he loved seeing her in a colour that represented him in a way), and of the style he wanted, and of course he knew her size, because she told him that when she told him he had to buy her a dress. That conversation was accompanied by a lot of babbling actually. He had to buy her the dress, but of course he wouldn't have to pay for it, she would pay him back, and she would need underwear too, but he didn't have to buy that she would do that herself. Oh and jewellery, no, that wasn't a hint, she could take care of it herself. But Oliver had assured her that he would of course pay for her dress, that wasn't a problem, he asked her to go with him of course. If she wanted to, he could buy her underwear as well, and jewellery he would certainly take care of, no questions asked. But Felicity insisted (accompanied by another babble) that she would buy her own underwear, because that would be waaaay too awkward, if he were to buy it.
And now that he was in the dress shop, he was glad she had insisted. Because he found it hard enough to pick out a dress as it was, let alone he had to have bought her underwear. He wouldn't have had a clue! The assistant had already asked him if he needed any help, and he said he was looking for a very special dress, preferably emerald, and it had to be long as well. The price didn't matter to him, as long as it was special, he said, and she had went to pick out some dresses which he could consider.
When he finally found a beautiful special dress he liked, and which he thought would make Felicity look amazing (which she always did in his opinion, but well, this would make heads turn), he decided to go the family vault to look for some jewellery to accompany this dress.
After he had spend another hour at least looking for jewellery, he had finally found some pieces he really liked, and wouldn't overwhelm Felicity too much.
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The next day, he decided to ship the dress to Felicity's desk, so she would have a surprise during her working day. Also, this granted him the opportunity to see her first reaction, since his office walls were made out of glass. When the package arrived, he saw her first reaction was surprise, as she noticed the package was for her. Then it was amazement when she opened it and saw the dress, the shoes which went with it, and the jewellery he had chosen to accompany it with. And then there was the furious, though thankful and happy look she sent him. The furious look because she didn't want to be spoiled by him, the thankful and happy look, well, for obvious reasons.
He went over to her desk and asked her: 'Did I do well?' When his question was answered with a very wide smile, he knew her answer.
When he saw her walking down the stairs of her apartment building that evening, when he came to pick her up, he was amazed by how beautiful she looked. The dress fit perfectly, and while he didn't particularly enjoy shopping for it, he loved how she looked in it. He greeted her with a peck on her lips, at which she sucked in a breath, and he saw the look of surprise on her face. But he told her: "I told you you were going to be my 'date' date for the evening, and I plan to enjoy every second of it. And if you want to, I want to enjoy more evenings like this. I really enjoy spending time with you Felicity and you look beautiful tonight, every day and every night actually, and I would love to spend more of those days and nights with you, if you'd let me." She replied by giving him a kiss.