Disclaimer: Dean Devlin, TNT, et al, own Leverage. I'm making no money from this.
He knows he talks about his Nana a lot, makes it sounds like she was the greatest maternal figure to ever walk this earth. He wants to make sure Parker, and to a lesser extent, Sophie, know that there are good childhoods out there. Everyone knows Parker had a lousy childhood, even if they don't know the particulars. There was just something about Sophie's reaction to that martial arts promoter that made him wonder.
And Nana was wonderful, to him and the others she took in. She fed him, clothed him, and put a roof over his head. She tried to teach him right from wrong and she tried to show him she loved him in her own rough way. So maybe all the right and wrong didn't quite stick -- there were a lot of kids for his Nana to worry about and she didn't always have time to focus on the details.
After all, he wasn't the worst. He was smart, which was part of his problem, but he wasn't getting into fights. He wasn't the kid who got her called down to the school to discuss suspensions. He just sort of blended in.
So yeah, he had a good childhood, at least compared to Parker and maybe Sophie. Nate, he thinks, had a good childhood. Eliot kind of seems balanced, so if he had a crappy youth, Hardison can't tell.
Nana was great and after meeting Parker, he knows it could have been worse. But there was still something missing. It's not until he's spent time with Nate that he knows what it was.
Until Nate and the team, no one ever relied on him to be the one to fix everything. They'd use him for his computer skills and then leave him behind. That's all anyone ever saw.
Nate sees more. Nate has let him do some grifting, and okay, the Russian mob thing was a mistake, but Nate trusted him enough to let him try. No one has ever put more pressure on him than Nate. Stop the plane from blowing up, was the order. And he did. Not just pretend to be a lawyer. Actually be a lawyer and by the way, don't just bore the jury, win them over and win the widow her civil suit. And he did, and Nate told him he could do anything he put his mind to.
Yeah, his Nana was the best mother he could have asked for. But Nate was the best father.