(If you don't support the headcanon names for Bro as Dirk and Grandpa Harley as Jake, I'm sorry.)
A lot can happen in 5 years, and in 5 years Bro went from a player that jumped from person to person to a man that was tied down with the love of his life. He never thought that relationships were for him, love just never happened to him. That was until he met Jake. He was the polar opposite of Bro, but as they say opposites attract. They were inseparable, and the jokes about Jake's age and the whole "Til death do us part" bullshit never crossed Bro's mind. Never until all the jokes became reality.
Jake's old age came and bit him in the behind eventually, a slip in the kitchen and a broken hip, lead to an infection, and eventually death. Dirk never left his side the entire time Jake was in the hospital. He sat there, holding hands with the man he loved, he even slept in a chair beside his bed. It did wonders for Dirk's back ,and he could care less. It was 12:40 in the afternoon, the sunlight was shining softly through the curtain, when Jake breathed in his last breath, green eyes going slightly dull, losing their sheen.
Now, here Bro was, leaning over the coffin of his lover. His jaw set tight as he felt a feeling crawl up his throat he never thought would. He leaned down, placing a hand to Jake's cold cheek. It didn't seem right, it just didn't. Dirk inhaled a shaky breath, laying a kiss to Jake's lips,
"Please don't wait, I know you won't listen but it's ok to go on." Dirk stood up, bringing a gloved hand under his shades to wipe away the tears that were forming in his eyes. He felt a hand on his shoulder, looking over to see Dave,
"It's ok to cry Bro."
"Crying isn't in the Strider dictionary-"
"Bro." He looked over, seeing a sincere look in Dave's eyes.
"…You never speak of this again. You got me?" Dirk rested his head on Dave's shoulder, pulling the other into a tight embrace.
It was a crisp Autumn eve, two men bump into each other purely by chance. To any normal person this spot would hold no significance, but 50 years ago at this very spot, in front an old outdated bench right on the water front of the park was where two men had their first date. The park hadn't changed much, just the names and faces of the people.
"Sorry! Didn't mean to knock you down, here let me help you." The black haired lad extended his hand to the blonde haired boy whom was knocked flat on his behind,
"It's cool, thanks." He accepted the gesture, dusting himself off. The two lock eyes, time seems to stop, as if they were the only two in the world,
"H-have we met before? I'm Jake, Jake English." Jake extends his hand again, and the blonde eyes him before returning the handshake,
"Dirk Strider." Their hands drop, but don't pull apart. They glance down, and then back at each other before each returning their hands to their sides and look away, flustered.
"If you wouldn't mind, would you like to go for a coffee? I know a shop right around the corner. My treat." Jake chewed on his lower lip, nervously adjusting his scarf,
"That sounds just lovely, ."
50 years prior
"It's quite lovely, don't you think?" Bro make a noise, Jake always had to find something cheesy to say about every situation. They decided to come to the park that just recently opened up, perfect for a first date. Jake rested his hand on top of Bro's, sending a warm smile,
"You gotta shave the mustache sometime dude, staring to show your true age."
"And you're one to talk, Dirk. You have the 5 o' clock shadow going on."
"I make it look good."
"Are you saying I don't?" Jake feigned being hurt, placing his hand to chest, Dirk leaned over pressing a quick kiss to his lips,
"Never said that."
"Well Dirk, how would you like to go to the coffee shop a few blocks down? My treat."
"That sounds just lovely, Mr. English."