If he could get a message from his late wife, what is something he hopes his late wife is thinking about him and his life now?
The general message would be: " Look at you , tiger, swing those hips, you got this sugar. I've peaced out, don't look for me anymore."
If he could get a message from Sasha, it would be to confirm that she is in fact dead, as he never got that closure. She was MIA and then declared dead a year afterwards. There is no body, her casket is empty. Even now that he has made peace with it, there is the lingering thought that maybe she's still out there.
Which in turn remains his only and true regret, he has always felt like he abandonned her, gave up on her, because he was unable to go look for her. He tried, almost a decade later, but he could not go to the site of the bombing and most people he had contacts with locally were dead or had moved.
Generally, Jack knows Sasha would be proud of his life now, of what he has achieved and how he carries himself despite having been utterly destroyed physically and mentally. She probably would find him also really attractive still.
The message would be: "It's okay sugar, let go, it's okay to let me go. "
She would also tell him to let go of her, especially on main since he's still carrying his wedding band. That it is okay to let her go and rest, that it's okay to fully mourn her and close that chapter of his life and open his heart to maybe someone else.
The message would be : Dayum, sugar, got some cuties going for you, huh? Good, get some loving into your system, god knows you need it. "
May it be with Robby, Wanda or Samira, he's not able to take the ring off just yet. There is no competition, just he keeps it as a reminder of what love lost feels like, mostly to hold on to the love given by his significant others. There is still so much guilt in moving on with someone else, despite him knowing that Sasha would have wanted him to.
specifically for XY verse since she knew Weylen: "Tell Weywey I owe him one. Go for it sugar, couldn't leave you in better hands than his."
The only verse he has truly put the wedding ring away in a box and build a different life. It took the longest time for him to get over the guilt and grief to even accept Weylen and tell him he loved him in a way that did not feel hallow. Jack, as much as Weylen, are painfully aware that in a way, had Sasha not died, their story would have never bloomed.