Killian groaned at himself as he watched Emma and Henry walk away from the house. He'd made a complete fool of himself by voicing his opinion on Swan's date and knew he was close to revealing that she shouldn't go because she should go on a date with him. He was an idiot. Killian had given up on the hope that Emma Swan felt something for him long ago, back when they were still in high school and she was his brother's beautiful best friend. Well, she was still his brother's beautiful best friend, even more reason to steer clear of her instead of pursuing her like he really wanted to.
He could have been sure he'd seen a flicker of interest when he had first arrived home but he wasn't sure if it had been wishful thinking on his part or just the same fleeting look of interest that he seemed to inspire in women these days. He knew, as the years went by, that he had gotten more attractive, knew that he was appealing to women, Milah had told him as much and often.
Killian squeezed his eyes shut as the pain of Milah crept in. He had told himself that he wouldn't think of her anymore, that he was coming home to escape her, to seek comfort in the familiarity of his brother's company. The time for mourning that relationship was past, she had made her choice and he had vowed to accept it. He hoped that his brother hadn't figured out too much of why he had come home, unsure if he was ready to talk to Liam about his failure just yet. Another way of letting his brother down. And worse still, Swan would find out, Liam had never been able to keep any of his worries about his younger brother a secret from her and Killian wasn't sure he could take the look of pity coming from her. Thinking of Emma again reminded him of her date with Humbert and he groaned again in annoyance. His annoyance soon gave way as a plan formed in his mind. Reaching for his phone, he smirked as he brought up his call list. If he couldn't date Swan, then he was going to have to find a date of his own.
Killian smirked as he walked into the restaurant with Jessica on his arm. Or was it Jessie? He tried to be more attentive, some part of him knowing this whole plan was ridiculous. A quick phone call to Victor had been all it had taken to get him set up with a date for the night and after some careful questioning around his brother he had found out exactly where and when Emma and Humbert had their date. So here he was, two days later, with a girl on his arm, stepping in to the very place that Emma Swan would be arriving at shortly for her own date. He placed his hand at the small of Jessica's back as he steered her towards the bar thinking back to the other day when he had found out that Emma had been asked out. He had purposely misled Liam into thinking he was going on a date that night when, in reality, he had been going to catch up with Belle, following her divorce. He and Belle had always gotten along and he often met her for coffee on his very brief trips back to Storybrooke to visit his brother. He had always managed to miss seeing Swan on his return journeys, although did see a lot of her son, Liam normally looking after him while he did paperwork for his business while Emma was at work as the sheriff's deputy. He liked spending time with the lad, he was funny and smart and reminded Killian of his mother in a lot of ways. He tried not to wince whenever Henry mentioned his father who, Killian knew from Liam, was an inconsistent part of the young boy's life. Killian didn't like the idea of Neal still managing to have some kind of contact with Emma but knew it was good for the lad to be able to see the man, whether he warranted the title of father or not. Killian had always thought that Liam was more of a dad to Henry than Neal was and he had a sneaking suspicion that Emma would agree with him.
Killian started when he realised his date had been talking to him and quickly shook his head to rid himself of thoughts of Emma Swan and her ex-boyfriend so he could pay proper attention to the red head in front of him. He managed to lose himself in conversation for long enough to miss Emma's entry until she was seated at a table waiting for her date. Killian waited until the sheriff had arrived before grabbing his drink and looping his arm around Jessica's waist, leading her towards Emma's table. He eyed the curly haired man sitting opposite her and had to begrudgingly admit that he wasn't actually terrible looking. And if he was as nice as Liam said he was then Killian was sure that he was definite competition for Swan's affection. Not that he was actively pursuing her. No. She was just his brother's beautiful best friend. He placed his drink soundly on the table, a little rum spilling over the edge and onto his hand. He quickly sucked the rum of the space between his thumb and forefinger as Emma's eyes darted up to him, unconsciously tracing the movement of his mouth.
"Swan!" He tried to sound more surprised than he actually was (which was not at all). "Fancy seeing you here!"
He unwound his arm from his date's waist to wrap his fingers round a chair at a nearby empty table, dragging it closer until he was seated next to Humbert. He used his foot to loop around the rungs of the other chair, tugging it over and next to Emma, before gesturing to Jessica to sit down in it.
"Yes, Killian, what a surprise that you found me in the exact place that I said my date would be at." Emma deadpanned, raising an unamused eyebrow at Killian.
"You never told me where your date was going to be, love." Killian answered honestly, raising both eyebrows as he took a swig of his rum.
"And I'm sure your brother didn't tell you, did he? Because Liam Jones is so well known for keeping other people's secrets to himself." Emma narrowed her eyes at him suspiciously.
"Liam Jones?" Killian had almost forgotten about the sheriff sitting to his right until he spoke up. "Your Liam's brother?"
"Aye, for my sins." Killian nodded solemnly before sticking his hand out in front of him. "Killian Jones."
"Graham Humbert." The sheriff told him, as if Killian didn't already know who he was, taking his hand and shaking it firmly. "And you are?"
"Oh, this is the lovely Jessica." Killian smirked salaciously at his date, causing her to blush and duck her head as Emma rolled her eyes. "My wonderful companion for the evening." Killian flicked his eyes up to Emma, wanting to see her reaction but she had her face hidden in the menu. "So, have you pair ordered your food yet?"
"No." Emma answered, eyes pleading with Killian not to do what she knew he was about to. "We've only just arrived. On. Our. Date." She said the last part slowly, hoping it would put Killian off his plan, but she could tell by the look on his face that she would have no such luck.
"Excellent news!" Killian exclaimed as he pushed himself to his feet. Emma let out a breath of relief, as he moved away from the table only to glare at him when she saw him grab the edge of the empty table next to them before dragging it closer. "Grab the other end of this, Jessica, love, we'll have a double date!"
Killian sat back in his chair, tables now repositioned so they made on large one, before shooting a grin at Emma who only glared back. He picked up his menu, throwing her wink over the top of it and leaning back in his seat.
"Now then, what's good here?"