Dean had a habit of making people love him despite his gruff ways. Jack was a shining example of this. He was terrified of Dean at times and yet, Dean was the person he immolated the most in his formative days.

"Nice to meet you, Jo." He spoke, that earnest look refusing to fade. "It was May 2020." He wasn't giving the full date, he had his own reasons, but it felt more enough. "What year was it for you?" He assumed she was from the past.

Mostly since they may not have a future.