Though I've got a headcanon for Paul that you can pry from my cold, dead hands—and despite the fact that I absolutely maintain that the entirety of AYITL does NOT count as canon—I've got an alternative for the Paul fiasco that I like better, in terms of forgettable love interests...
I wish that these two had moderately hit it off after Richard's memorial service:
...bonding over Star Trek, discussing insurance, hatred of golf, comparative fishing experiences, only for Lorelai to come upon their conversation and be unnerved.
Lorelai: "Don't you remember, this was the guy, Luke—the one at the Dragonfly's trial run??"
Luke: "Wait—you mean the guy that (references completely different guy at completely different big Dragonfly event)."
Lorelai: "No! You remember! The guy you were so frustrated about just before the first time we—"
Jason: "Hold on—are you two together?"
Lorelai (to Jason): "Oh my God! This is Luke, Luke from Luke's diner—do both of you have early onset dementia or something?"
Jason: "You mean, this is Duke? You got together with Duke?"
Luke: "For a lot longer than you were around."
Jason: "I wouldn't be so sure of that. I knew her when she was in braces."
Lorelai: "No one—no one is allowed to remember that. Why do you always remember the worst things?"
Jason: "No, the headgear was the worst."
Lorelai: "Okay, you officially do not exist."
Jason (to Luke): "You see how quickly she can dismiss you if she doesn't get her way?"
Luke: "Hey—you're talking about my fiancée."
Jason (to Lorelai): "Wait, I thought you got married."
Lorelai: "Everybody thought we got married. To the point that we basically are married."
Luke: "Except in the eyes of the state of Connecticut."
Lorelai: "Who cares about the state of Connecticut?"
Jason: "Depends on whether it's an election year..."
Luke: "I got you a new ring."
Lorelai: "Wait—what??"
Luke: "A long time ago; but since the setting-the-date disaster and the venue disaster and the apple-cravings disaster and the mass Gilmore invasion disaster and Town of Stars Hollow vs Taylor Doose disaster, and...."
Lorelei: "Yeah, I get it, our timing has always sucked—but there's a ring?"
Luke (reaches into his pocket but stops): "I can't give it to you at your father's—"
Lorelai: "Screw timing!" (people look at her funny) "Okay, maybe not this minute—but the wedding is back on. And you owe me a ring, mister."
Jason: "Glad I could be of service."
Lorelai (to Jason): "How are you still here??"
Jason: "I haven't teleported away."
Luke: "Who is this guy again?"
