Summary: "Come on Felicity, two weeks in Hawaii while you pretend to be my ex-wife, what can go wrong?"-Just Go With It AU.

A/N: So this is an idea I had, to combine Olicity with the hilarious movie that is just go with it. Also known as how many Lord of the Rings references I can fit in one fic. Hope you enjoy :)

Disclaimer: I, in no way, shape or form, own Arrow or Just Go With It.

(prologue)

In all honesty, he had seen this coming. There had been all the signs: the nonchalant meeting, playing hard to get, making him pine for her like some love sick puppy. It was cringe worthy to even think about. She was a pro, he had to give her that. Who would have thought that Oliver Queen would have fallen for a gold digger? A gold digger he'd only met six months ago at a company benefit and was meant to marry two an hour ago. No, Oliver Queen didn't do marriage. How she'd manipulated a proposal out of him, he would never know.

"At least you found out before you said your vows. Saves you the trouble of forking out on the divorce," Tommy said next to him. Oliver mumbled something incoherent and downed his beer. They had been at the bar for the past two hours since the two of them had bolted from the hotel and there had definitely not been enough alcohol consumed to get Oliver to talk about the fresh wound left by Helena Bartinelli. Two hours ago, he had honestly thought he'd been in love, about to get married to a gorgeous woman who had somehow stolen his commitment-phobic, playboy heart. And now...now he had an idiot best friend spewing out bullshit in order to make him feel better and two rings that were supposed to belong to the future 'Mr&Mrs Queen'.

"You're really not helping," Oliver growled and continued staring at the gold bands in front of him. How could he have been so blind? Everyone had been warning him against marrying Helena, but God forbid Oliver Queen listen to anyone but himself.

"Even Felicity told me not to marry her and that girl can't find a fault in anything," he exclaimed, signalling the bartender for another round. More beer, that was definitely what he needed.

"Except for clowns, kangaroos and my father," Tommy corrected, earning a glare from Oliver. "Listen mate, these things happen. The good thing is she didn't take anything of value."

"Except my dignity," Oliver amended with a load groan and his best friend shrugged. Looking down at the rings once again, he realised he was actually glad, for the first time since he'd realised Helena's true intentions, that he didn't get married and not because he didn't have to pay a divorce settlement. The rings they would have worn as husband and wife had originally belonged to his grandparents who had had the most loving relationship he had ever known. The two had died within days of each other, both wearing the rings that had been on their fingers for 68 years. If his grandmother had known that Helena almost wore her wedding ring she would have turned in her grave and proceeded to haunt him.

"Too much beer, I need to hit the can," Tommy said and then suddenly Oliver was alone. Well, not completely alone. In fact the bar was surprisingly busy. Gulping down another beer, he placed his grandmothers ring in his wallet for safe keeping, not wanting to risk losing it, however he kept glaring at the larger shiny band that mocked him.

"Is this seat taken?"

The woman is gorgeous. Completely stunning. Her dark hair was curled softly and she was wearing a dark blue dress that went down to just above her knees. She was definitely the kind of woman that pre-Helena Oliver would go for. Drunk, heartbroken and desperate, he shook his head and the woman took a seat.

"I'm McKenna," she told him before asking the bartended for two more beers.

"Oliver."

"Are you ok? You look kinda sad," she asked with a sympathetic look on her face which made Oliver internally grimace. If there's one thing he hates more than gold digging fianc- ex-fiancé, it was being pitied.

"Not really. My..." he trailed off. The story is pathetic and so incredibly cliché that it made him sick just to think about. What would the woman in front of him think if he told her that he, Oliver Queen, typical trust fund brat, had fallen for a money scheming, supermodel looking bitch that he would have married and be dancing at their reception with right now if he hadn't over heard her with her girlfriends talking about her devious plans. She would laugh in his face and find someone who wasn't an idiot to occupy her time with.

"I caught my wife cheating. With the pool boy," he lied He watched as one the girls eyebrows raised in shock and a look of complete sympathy appeared on her face. "I mean, I shouldn't have been surprised it's not the first time but we were doing so well together. Guess nothing good lasts."

McKenna clasped his hand in hers and looked at the ring on the bar. "Why don't you leave her?"

"The kids," he said and tried to keep a straight face at the way she was believing the complete and utter bullshit coming out of his mouth. Kids? Oliver Queen didn't do kids. "It would crush them. But I just... I want to be happy again, you know. Actually, I can't remember the last time I smiled."

McKenna squeezed his hand tightly and picked up the old ring before placing it in his hand. "How about I try and out a smile back on your face, huh?"

"I think you already have," he laughed and followed the brunette out of the bar, catching Tommy's awestruck face from the bathrooms exit. Maybe the day wasn't quite as terrible after all.