After a few more 'coincidental' encounters at Karen's, Dean finally worked up to nerve to ask Brooke out. Lucas overheard, and snorted with laughter before heading back into the kitchen while Brooke rolled her eyes and turned back to Dean, who seemed confused.
"Ignore him, he's just jealous." She said, shaking her head and giving him a little smile. "So, you want to take me out?" She asked, amused.
"Trust me, if I didn't want to, I would not have asked." He said with a little grin back at her. "Seriously, Brooke, come on. I'm tired of playing the 'only if we meet again' game. Just let me take you out. Dinner and a movie. Or just dinner, than a walk through the park or by the river." He said, making a mental note to never ever tell Sam that he had actually put his dating advice into use.
Brooke smiled again and shrugged a little, before she sighed. "I suppose I could try to make some time to go on a date with you." She said, before she bit at her lip. "But there is a condition; you have to answer every question I ask all night. It's either that or no deal." She added in quickly.
Dean hesitated. He wasn't sure what kind of questions she would have, but he eventually laughed and nodded. "Yeah, yeah, fine. I can't guarantee that I'll give you good answers, but I promise to answer every question you ask." He said, not being specific about if he would answer truthfully or not, because he couldn't be positive that he wouldn't have to lie
"Good." Brooke grinned, triumphantly, satisfied with his answer before she stood and leaned over to kiss Dean's cheek. "I'll see you tonight. My place, eight o'clock. Do not be late, Dean Winchester!" She called, and Dean couldn't help but just nod after her, before he realized he had no idea where she lived. Haley walked over a minute later with an address scribbled down on a napkin, setting it down in front of Dean before taking his plate and looking him in the eyes.
"If you hurt her, Lucas won't be the only one who hurts you, understood?" She asked, and Dean had to admit that he had never been more scared of a civilian than he was in that moment. He nodded slowly and Haley smiled at him, before she patted his shoulder. "Great. Glad we're on the same page. Have a nice night tonight."
Eight o'clock finally rolled around and Dean pulled up outside of the address Haley had given him, checking his hair in the rear view. Then he got out, straightening out his clothes as he walked up to the door, but before he could knock, Brooke pulled it open and grinned at him.
"Eager much?" He asked, playfully, to which she scoffed. "I mean, I know I'm pretty irresistible, but damn that was a quick reaction time."
"You wish. I was worried you were too intimidated to show, so I've been people watching to see if you actually came." She replied, pulling the door closed behind her and crossing her arms over her chest. Dean grinned.
"Huh. Well then, uh, surprise!" He said, throwing his arms in the air, to which Brooke rolled her eyes and walked past him with a shake of her head.
"Come on. I'm taking you to a nice place in town for dinner." She said, pulling open the passenger door to the Impala, and Dean frowned after her.
"But I'm the one who asked you out." He said, following after her and climbing into the car as well, still looking at her with a frown.
"Which was sweet. But I've lived here my whole life and you're just passing through, so I think I know where the good food is." She responded, smiling at him sweetly, to which he rolled his eyes and closed her door behind her, unable to come up with an argument against that logic.
He ended up loving dinner, and didn't even care about how high the bill was when it finally came. They had each had a four course meal, though how much of it was actually eaten was subject to debate. And on top of that, they had a bottle of wine, so he couldn't complain with the price when the check came, given what he;d been expecting. He charged it to his card, which seemed to take Brooke by surprise.
"You make a lot of money?" She asked, tucking her own wallet into her purse, as though she thought she would have to pay. That confused Dean a little, but gave him enough time to think of an appropriate answer.
"It's a family business. We sort of have a lot of, uh, investments." He said, which was not a complete lie, as long as you count identity fraud as an investment.
"Huh." Brooke said with a smile, before the waitress returned with the card and bill. Once Dean put his card away, he stood and held his hand out for Brooke.
"Walk along the pier, now?" He asked with a grin. She took his hand and smiled at him again, before pulling him close and leaning into him.
"You're one big surprise after another, aren't you?" She laughed a little before letting him lead her out of the restaurant and down to the pier where they walked for a while before she sighed and looked up at him. "I didn't ask you many questions tonight." She pointed out.
"Do you have a lot? You could still ask me." Dean said, once again not mentioning if he would answer truthfully or not. She was quite for a minute, before she took a deep breath.
"Do you travel around a lot? Or is this just a road trip to find your dad?" She asked, finally.
"My dad travels a lot. Used to drag me and Sam around with him when we were kids, and we never really stayed in one place for too long. Once you're in that habit, it's hard to break. So I do travel a lot, yeah. This is Sam's first road trip with me in a while, though." He said, stretching a few truths but trying to keep things from complete lies.
"Do you ever go to the same place more than once?" Brooke asked, quietly. Dean sighed and looked down at her with a little smile.
"Usually? No. But….. Tree Hill might just become the exception to that rule." He said, before he shrugged a little. "If you do want me to come back, that is."
"Oh, I think I do." She said with a grin, before she leaned up and pressed a soft kiss to his lips, which made him smile wider.
"Well then this will definitely not be my last trip to Tree Hill." He said with a smile, before they continued along their walk. Brooke leaned herself into more into his chest at his affirmation of a return, feeling a comfort in knowing that Dean was ready and willing to come back to her town to see her in the future.