It started with a bite of his burger, and it caught Dean's eye. He can see Jack taking as just of a big bite out of his burger as Dean did. The elder Winchester just batted an eye as he took a sip of his beer, Jack taking a sip of his own water at the same time, before they both set it down at the same time. Something in him, it reminded Dean of Sammy. How when Sam was younger, he'd always copy Dean until he wrecked the younger Winchester.
To test this, Dean grabbed his beer again, leaning back in the chair. He glanced over at Jack, seeing the young nephilim doing the exact same thing. “Stop.” He said sternly, looking right over at Jack. The nephilim stared at Dean, before taking a huge sip of water just as Dean took a huge sip of beer. “Okay that's it-” Dean grinned and tackled Jack after their drinks were placed down, again, at the same time. Jack squeaked as he was pinned down, looking up at the elder Winchester with wide eyes.
“Y’know how I dealt with Sammy when he pulled this shit?” Dean asked with a shit-eating grin. A bit confused and startled, the nephilim shook his head. “No.” He replied. “What did you do?” He asked, curiosity sparkling in his eyes. “This.” Dean replied before tickling his sides. Jack immediately erupted into laughter, trying to push his hands away from his sides. “Dehean- ihit tihickles!” Jack giggled out. Dean couldn't help but smile at that, chuckling softly to himself. “If you're laughing this much over just the sides, I'd love to see how you laugh when I get your worst spots.” He teased before digging under his arms. Jack squealed and threw his head back in loud laughter. “DEHEAN NOHOT THEHERE PLEHEASE!” Jack laughed loudly with a snort. Dean started laughing himself at that. “No way! Did you just snort? Man, I gotta tell Sam and Cas when they get back!” He chuckled. “Didn’t know you and Sam had the same weak spot.” He grinned mischievously before letting up a few minutes later.
Jack grinned and caught his breath, panting softly when Dean finally let up. “That was fun.” The nephilim smiled a little, causing Dean to grin. “Just like Sammy, he used to love when I played tickle monster with him when he was little.” He informed, taking a sip of his beer as he sat back down on the motel couch. “He did?” The nephilim asked with a small smile. “He sure did. Maybe I can teach you a few pointers to tickle Sammy.” Dean chuckled as his attention turned towards Scooby Doo, which was playing on the TV. Jack smiled as he recovered from the tickle attack, his attention turning towards the TV too, as he leaned his head against Dean's shoulder. Maybe he did belong with them.