The first time Jesus said it, he did so dramatically and with Daryl standing right there.
"If I don't make it back," Jesus sighed, hand going to his heart as his body tilted to the side while his other arm reached out as if to grasp feebly at Daryl, who stood a good fifteen feet from him and the car, "Tell Daryl I love him."
The tension the group had been feeling broke in that instant, a cascade of laughter from everyone except Daryl. But even he was fighting a snort of amusement and had to settle on a heavy eye-roll and muttered, "Shut up, prick." that held no malice.
Jesus slid himself into the passenger side of the car with a shit-eating grin as Michonne said her own private goodbye to Rick before she, too, got in the car.