Alfred loves pissing Bruce off by unhelpfully reminding him that his children are growing up, in part because this was also his form of humor when Thomas was around and Bruce was the child being raised with love, but also because it's the easiest way to emotionally ruin Bruce without being mean
Like imagine new parent Bruce holding a sleepy 9-year-old Dick in his arms and cooing "Alfred look at his dimples 🥺"
And Alfred gets the mischievous break in him, the one he was certain died with Thomas and Martha, as he smiles and goes "Yes, I'd imagine his future lover would find them just as endearing"
Bruce pauses. Starts tearing up. Alfred is trying not to laugh.
It continues when Bruce adopts Jason.
The worst of it happened when Bruce was first helping Jason into the uniform boutique to get suited for his first set of academia wear. Bruce is gushing because "Look at you, Jaybird! My handsome, handsome boy 🥹"
Alfred unhelpfully butts in, adding, "You are truly stalwart, Master Jason 😊 I can perfectly picture you in graduation robes in these same colors"
Bruce starts ugly wailing in the middle of the boutique. Jason offers to call Dick because "he'll know how to calm Dad down!! 😰"
Then Bruce starts crying harder because Dick is all grown up, and if he sees his baby and his babier baby together, he might just pass out
For Tim, it happened quietly, because losing his second son altered the way Bruce showed love (but it was love nonetheless)
Alfred didn't even mean for it to happen this time, because he thought it would do well to retire this kind of humor after the cycle had been complete with Bruce losing both one father and one son.
Tim was just putting his first line in the family height doorway since getting adopted. Alfred makes a loud observation, "You are much taller when you arrived in this family than Master Dick and Master Jason had"
Bruce teared up quietly... then promptly picked Tim up and hugged him like an overgrown floppy teddy bear. Tim is just "Welp! This might as well happen 😃"
Somehow it got worse with Cass because of the fact she was his first daughter, and Bruce is not ready for anything about it
Alfred mentions letting Cass pick out items from the family jewels for her first appearance as a Wayne. He goes into full detail about how Cass picked the most beautiful diamond necklace, and how she might want to consider keeping it for her future wedding because it's the set of diamonds that go well with anything white
Bruce is seen curled up on the floor. Cass comes in, reads her dad's body language, and looks Alfred dead in the eye while saying, "You are an evil man"
Damian is warned of Alfred's choice of humor around Bruce, but it doesn't make it less disconcerting when it finally happens to him.
He and Jon had gone up to Bruce to ask if they can take the bus to the city. Bruce is fretting and all, never mind the fact that his son was a trained assassin being escorted by a honed Kryptonian.
Alfred is nearby, and gears up to drop the worst line ever:
"Honestly, Master Bruce 🙄 it's as if Master Jon just asked you for Master Damian's hand in marriage 😑 Just let the lad go, sir 😒"
And Bruce face goes from serious, thoughtful dad, to a snotty, ruined, curled up mess
Damian is distraught. "PENNYWORTH, WHY WOULD YOU SAY THAT!?"
"I believe this is what you kids call... for the love of the game 😌"
Bruce pulls Damian on his lap, pouting "Dami you can't get married until you're 30 🥺 okay??? You'll break my heart 🥺 I just got you back in my life, I'm not gonna give you away again so soon 🥺"
Damian is blushing horribly, "Father, you almost married my mother at age 21, you're being ridiculous. Jon, get me out of here before my father thinks about screaming in anguish"
[Jon is rooted in place, blushing madly, imagining one day talking to his childhood crush's father to ask for permission to propose]
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