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Chapter Fifteen
Jackson hated that he sounded like aguywhen Oleander said they weren’t going to have sex. Sure, he was hoping he’d get laid, because he knew the food truck festival date was a special one. But he wasn’t actually that disappointed they weren’t going home together. No that was a lie—he was mildly disappointed. But it had been his best dateever.
His feelings for Oleander sometimes felt overwhelming. When he thought about her, Jackson’s heart would race and he’d feel his face stretch into a smile. Whenever she texted him, he’d drop everything he was doing to reply. There was something about the way she made him feel that he couldn’t put his finger on, but he didn’t need to identify it.
She made him feelalive.
But here lay the problem: Jackson had played his best hand with the food truck festival and now he was all out of good ideas. Jackson knew that Oleander wasn’t going to be the kind of woman who wanted luxury—she liked eating with her fingers, loading up on sugar and having a good time. She might have worn a beautiful dress, but she paired it with sneakers, because she was ready to spend time on her feet.
And he didn’t know how to date women who liked the simple things.
Thankfully for him, his friends had a poker night a few days after his date and Everleigh was coming. Everleigh had gone to school with the boys in Middletown, she and Milo had a brief relationship and when that ended, she’d become part of their bi-monthly poker nights.
As soon as Everleigh walked through the door of Milo’s apartment, poker was abandoned in favor of helping Jackson plan dates. She asked questions, made notes and discussed different places to go. By the end of the night, Jackson had a month worth of dates in hand and all he had to do was pick the best ones.
Jackson:Are you ready for my dates to rock your world?
Oleander:I’m actually kinda nervous now.
Jackson:I think you’re going to love them.
Oleander:Wait, you’ve actually planned a whole bunch?
Jackson:I got some help and enough ideas to last me a while.
Oleander:Wow, you weren’t kidding about wanting to go on dates.
Jackson:I want to spend as much time with you as I can and if that means multiple dates, so be it.
Oleander:That’s really cute.
Oleander:Do I get a hint of what I’m in for?
Jackson:Lots of fun stuff and a chance for us to get to know each other really well.
Oleander:Didn’t we already do that on our first date?
Jackson:Oh, this is a different kind of method.
Oleander:I’m excited!
Jackson:Meet me at the park where we had our first date, this Sunday, 9am. All will be revealed.
The first ofthose dates was paintball and because he didn’t know too many people, he invited Milo and Gavin to come along and told Oleander she could invite Frankie if she wanted. So at least they had a team of their own. He booked them a game and after picking the girls up at the park, Jackson drove them over to the venue. Oleander and Frankie had been far more excited than he expected, which was good. Because their team won effortlessly.
After paintball, they went to a bar close by and filled themselves up with food and beer. The five of them looked like they’d been through the wringer and were covered in paint, but they didn’t care. Even when other patrons glared at them for making too much noise or looking the way they did. Milo and Jackson challenged the girls to a round of pool, which ended with the boys losing. Oleander was competitive, but Frankie was a whole other level. Jackson liked that even though it was a groupdate, he got to see a different side of Oleander.
Dressed in shorts that flaunted her gorgeous legs and a faded t-shirt, she was aggressive, loud and so incredibly sexy. If he was being honest, he’d never noticed these things about women before, and Jackson was pretty sure he was never really interested in women with big personalities. But Oleander had him wrapped around the pinkie.
After the successful first date, Jackson had to shuffle his ideas. He found out when Oleander had her next evening off from the Barrel and signed them up for ‘Sangria and Strokes’ at a small art gallery in town. He didn’t care for wine, but it was the only drink they were offering. Besides, he figured they’d have a good time.
Oleander showed up in another dress and this time she’d paired them with heels and Jackson had to bite his fist at first sight—those legs,fuck, she was trying to kill him. After a quick walk-through of the gallery—where Oleander and Jackson kept touching and teasing each other—each couple was handed a jug of sangria that would be topped up as they finished it, and asked to sit in front of easels. The easels were angled in such a way that they couldn’t see what the other person was drawing, which was great, because despite being a designer, he wasn’t always confident about his art.
The theme for the evening was to paint something that represented your partner and all Jackson could think about was painting Oleander as she was. He had never done anything like this before, and he knew the idea was to paint her without paintingher. She poured them both a glass of sangria and tied her hair up as she got to work. Jackson’s eyes followed the shape of her neck, imagining what it would feel like to press his lips to the spot where her neck met her shoulder. It took everything in him to turn away, even though all he wanted to do was stare at her some more. The lady hosting the evening announced they had 30 minutes to do their paintings, after which they could all mingle and drink some more.
At the end of the 30 minutes, Oleander flipped her easel around to show him a splash of colors. It was a mix of browns and blues and greens and some red.
“It’s kinda hard to paint you when I’m still figuring you out.”
