Four Times Oliver Tried to Proposal to Felicity

(and one time he did)

1. Unfair Timming

Oliver and Felicity had been dating for 6 months now and he decided that he didn't want to live his life with anything other than his IT girl. So, that's how he ended up here waiting for Felicity in the foundry with a ring in his pocket wearing his nicest suit. After weeks of planning and help from Diggle he had came up with this perfect proposal. He would wait for her here and blind fold her so it would be a surprise. Soon when they got to the spot on the beach where a small table was set up they would have a wonderful romantic dinner, and afterwards just as the sun was setting he would propose.

It was about 5:43 and he had planned to leave at 6. Suddenly he got a text from Felicity:

Got held back at work... :( won't be able to meet you at the foundry. Sorry! Will you be alright without me?

As much as Oliver wanted to text her 'no' and 'come to the foundry because I've been planning this thing for weeks' he ended up texting:

Yeah, crime's at a low and I'll just pick up some take out

Seconds later Felicity had texted him back:

Thanks, see you at home. XoXoX

Oliver let out a sigh and pulled out the velvet box. He opened it to reveal a perfectly cut, simple ring with a medium sized diamond on a sliverish band. He got out his phone and started to text Digg:

Planned failed. Felicity was held back at work.

When Digg had replied 'LOL' to him, Oliver couldn't help the clench of his fist.

2. Post-It note

Oliver soon comes up with a more...unique way. He remembers how she used to love to leave sticky notes on his desk at QC and the idea hits him. So that night when he went to the layer he grabbed the bright pink post it notes and scribbled in dark green ink 'Will you marry me?' he also added a very large smiley face. He walked over to her computers and stuck it next to the mouse and waited for Felicity to come down while sharpening his arrows. The moment she came skipping in the lair, Digg following behind, his heart started to beat faster and faster.

She sets down her coffee right next to the mouse...ontop of the sticky note. He wonders why Felicity hasn't answered him yet and he walks up to her.

"Hey," He says slowly.

"Hey!" Felicity exclaimed.

"Did you get my note?" He asked and that's when he see's the coffee ontop of his sticky note.

"What note?" She asked. She see's Oliver staring at her cup of coffee and then notices a tiny bright pink corner stick out from under it. "Oh." She says as she reaches over and moves the coffee. Picking up the paper she read's it out loud. "Will you..." She looks at it for a while untill she gives up because she can't read the rest dued to how they're smeared. "What'd you need me to do?" She asked him. Digg's in the background shaking his head and smirking.

"Uh...I wanted to ask...if you could..." He looks to Digg for help but gets none and decides to just wing it, "Fix my laptop for me?" He asked wry. And he knows she knows he's lying because he doesn't have a laptop and so he tries to cover it up with another lie, "I mean I needed you to fix my laptop that I'm about to buy."

"If you're going to buy it...why would it need fixing?" She asked confused and Diggle's in the back laughing but trying to cover it up as a coughing fit.

"I don't know, Felicity! You're on an Island for 5 years and you forget this kind of stuff." He says trying to sound mad to make Felicity think he's joking.

"Okay, Queen. You get away with this one." She mummers shaking her head back and forth.

3. Sweet Swap

Okay, since the post it note didn't work he would just have to try harder.

"Felicity?" Oliver asked as he watched her work hard to find a lead on some criminal they were trying to find. The only response he gets from her is a 'hmm' but he takes it, "Remember how you always wanted to go to that Candy Shop with me and I said no?" He asked and at the mention of the Candy Shop her head spins around to face him her eyes wide, and it reminds him of a little kid.

"The one with hundreds of flavors of jelly beans! Sweet Swap, oh my gosh! Oliver can we-" He cuts her off.

"Yes, lets go." She shrieks with excitement, grabs her cardigan and runs up the metal staircase before he can even blink.

They park near the shop but far enough so that they can walk and pass by the little shopping stores as they go. Oliver runs through the plan one more time.

"Oliver?" Felicity asked worried,snapping him out of his thoughts.

"Oh, sorry."

"We're here!" She says. Immediately letting go of his hand and running inside. He's glad that it's not that crowded and then he gives the owner, who also knows the plan, a knowing look. While, Felicity is drooling over the variety of candy he slides the velvet box that holds Felicity's ring to the owner and he puts it on one of the rainbow lollipops. "Oh, Oliver, what do you think we should get? There's just soo much to choose from." She awes.

"How about a rainbow lollipop I saw in the display case by the counter?" He asked as he nervously glances at the ring.

"Nah." Felicity replies.

"Why?" Oliver asked alarmed.

"I don't really like lollipops that much." She shrugs as she grabs a back and starts stuffing pink tuti-fruity jelly beans into it.

"Well, how about we get one for Digg?" He asked, very determined to get her to at least look at the lollipop.

"Nah, he doesn't seem like a lollipop kind of guy." She says as she grabs a few gummy worms and also puts them into the bag.

"Well...maybe I want a rainbow lollipop..." He says crossing his fingers that this will work.

"Okay, go ahead, your paying anyways." She replies as she chooses between red or green sour straws and just picks both.

"Felicity, just do me a favor and at least look at the lollipops." Oliver sighs.

"Oliver, I really hate lollipops they make me nauseous." Felicity replied.

"Felicity go and look at the lollipop." Oliver says on the verge of his hood voice.

"No." Felicity says as she goes to measure her bag.

"Felicity just look at the-"

"NO! Lollipops and I...we don't - URGH!" She stomps out of her store enraged.

The owner looks at Oliver and gives him a sympathetic look and hands him the ring. He decides he'll just find another way and leaving a 20 dollar bill on the counter he goes off to find Felicity.

"Felicity?" He asks as he sees her looking at some puppies in the store window. She ignores him and is set on giving the puppies her full and undivided attention. "Fe-lic-ity." He says slowly and he's not surprised when she turned to look at him. "Could you tell me why you don't like lollipops?" He asks handing her the bag of candy and they sit down on the bench and watch the people and cars pass by in silence until she speaks.

"My dad...he gave me a rainbow lollipop before he left us when I were three." She sighed.

"Oh Felicity, I'm so sorry I didn't know." Oliver says, berating himself for not knowing and being stupid.

"It's okay." She replied. "Thanks for the candy." She smiles.

"No problem." He replies.

4. Classic Timeing

Oliver decided that he would just propose the old fashion way. So he picked her up at 6 o'clock with Roy and Diggle covering for him, and they went to the most expensive restaurant in Starling City.

It's after desert and he gets up to propose when a waiter bumps into him making the box fall under the table. He tells Felicity he drops his phone and goes to quickly grab it but when he looks up and is about to try again she gets a call.

It's Roy and they found a lead on the criminal they had been trying to catch and they have to rush back to Verdent, which is at the other side of town, and she's glad that they took his bike for once.

So she rushes out of there and is already putting on her helmet before he gets another chance to propose and he starts to wonder if he will ever get to.

5. The One Time He Did

Felicity is sitting on the couch watching her favorite disney movie, Lady and the Tramp, when Oliver comes in holding a very large, bright pink box with tiny holes in it.

"It's not my Birthday, you know." She smirks.

"I know." He replies simply.

"Then what is this?" She asked, pausing the movie, and motioning to the present he's holding in his hand. He drops it on the floor, gently, and tells her to open it. She opens it and gasp as she takes out a small white Maltese. "Awe." She sighs as she starts to pet the dog. "What's his name? " She asked.

"Her." Oliver corrects. "And it's Marry." He replied.

"Where'd you come up with that, Queen?" She asked as she looks at Marry's dog tag and then she see's it. On the back of the dog tag are the words "Will you 'Marry' me?"

She looks up and see's Oliver on one knee and tears start flowing from her eyes. "It took you long enough!" She says as she hugs Oliver and he slips the ring on her finger, but then he realized what she said and is very confused.

"What do you mean 'it took you long enough' ?" He asked.

"Well, I knew you brought the ring because...I manage your credit card account and I just didn't want to ruin the surprise soo..." She says smiling like a kid who knows they'll get in trouble.

Oliver shakes his head and sits down next to her and watches as the Marry gets to know her environment.

"So, are we keeping her?" Felicity asks and both her and Marry are looking at him with those big round puppy eyes and Felicity's lip is also quivering and he shakes his head while he chuckles.

"You both, are going to be the death of me." He laughs.

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