Consider: At their wedding, Jack actually cries a little more than Bitty? Like Bitty's a mess during vows and such, but Jack cries a little throughout the whole day, starting at the moment he walks out with Bitty in his arm, and realizes that HOLY SHIT he's married, he's actually married and Bitty looks so wonderful and Jack just can't believe it, and from that point he's just a tad misty eyed the whole damn day (I might totally write fic one day, so if it pops up again, you'll know I guess?)
OH NO THIS TOTALLY HAPPENS (Also yo I will be watching for this fic. I see you consider!anon)
Jack stays misty-eyed and then when his parents speak, he cries and Bob cries and Alicia wears away a tear but mostly just drags her husband up to give Jack a proper hug.
And when everyone is out dancing and they have finally gotten the chance to sit, Bitty looks over and sees Jack crying and smiling and laughing a bit and Bitty gets all flustered and a little worried. But Jack just waves him off and explains, “I’ve dreamt of this day so many times. I never dreamt it to be this perfect.”