Comforting the Young Sophmore

Dwight looked towards Tina longingly as she rummaged through her locker. With summer break approaching, he really wanted to say something to her. Maybe even ask her out if he could. But each time he tried he felt his nerve give out.
As usual, the girl headed out with her friends while Dwight was still unable to say a thing.
“Haaaah, I'm such a wimp...”
As he was about to crawl away in defeat, he felt a presence behind him.
“Staring again, kid?”
Dwight looked over his shoulder and saw the seniors' gym teacher standing behind him, a knowing smile on his face.
“W-What do you mean Mr. Kaysen?”
“Every day you come here and stare at that junior girl as she gets ready to leave.” He walked around Dwight, stopping in front of the boy.
“Are you just waiting for her to go,'Oh, I hope I get asked out this summer and even experience making love.' so you can dive in and go 'Yes, I'll gladly do both those things for you.'”
The boy couldn't help but giggle a bit at the voices the teacher used when saying those lines. But he had to admit, Mr. Kaysen had a point.
“Y-You're right. N-Not about the love making part, I can wait as long as I have to for that. But, the gist of it...”
The man tutted in disapproval,
“Waiting and hoping for the love of your life to fall onto your lap isn't worth a damn.”
“B-But she might—“
“Screw that nonsense!”
Dwight cowered from the outburst, something that was quickly noticed by the teacher. The man calmed himself before kneeling down, his hands giving the boy's shoulders a reassuring squeeze.
“I know you feel like you're nothing compared to her. And I know you're scared of being rejected. That's why you just hang back and hope that, somehow, someway, she notices you.”
Dwight nodded sadly,
“But listen to me, you shouldn't shoot yourself down, especially not with matters of the heart. Trust me.”
“Why should I? What do you even know about how I feel? You're the most vain and proud person in this school!”
George shook his head, still smiling,
“I wasn't always like this. Once upon a time, I was a lot like you, boy. And just like you, I watched my high school crush from the shadows, praying that one day he would notice me.”
He let out a sigh of nostalgia, clearly reminiscing of the past,
“But he never did. Instead, the class nerd was the one who worked up the courage to ask him out. He wasn't the proudest, nor the most handsome looking, but that act of courage won him my beloved's heart.”
“Did...did you hate that guy for it?” Dwight asked,
“Of course. After all, how could someone who hardly knew him, who never really talked to him, just come in and swipe the man of my dreams from me? But then I wondered 'what did I ever do for him?'”
Mr. Kaysen reached up and gently patted Dwight's head,
“I knew so much about my love, but he never knew me. So when would he have ever noticed me?”
Dwight sighed in defeat. He knew the point the teacher was making,
“Never, since you two never talked.”
“Exactly. So, if you've never properly introduced yourself to that girl, how do you expect her to notice you?”
“I...I'm still scared of her rejecting me. What'll I do then?”
Mr. Kaysen smiled,
“You let go. Not all love is meant to be, boy. Even more so at your age. There's a lifetime of people still ahead of you, and I'm sure one of them will feel the same way you feel for that girl.”
“I doubt you're being sincere with that last bit since you've got an ambiguous relationship with Dr. Archer and you're always trying to feel up Mr. Bennett.”
“I'm just putting on an act here. Truth be told, I've been seeing someone seriously.”
“You have?”
The teacher reached into his pockets and pulled out his phone, handing it over to the boy.
“See for yourself.”
Upon unlocking the phone, a chain of text messages appeared. The first few of the conversation were dirty enough to make Dwight blush—pictures included. But as he went ahead he could see the conversations change. He could tell that George and that other man were truly becoming close the more he read.
“You two are sickeningly adorable. Shame he isn't that first guy you fell for.”
“He isn't my first love, that's true.”
Mr. Kaysen took the phone again before standing back up,
“But I love him all the same. And I'm sure, if that girl rejects you, you'll move on and find someone else to love just as much as you loved your first.”
Dwight couldn't help but smile.
“Thanks for that, Mr. Kaysen. I think I know what to do now.”
“Glad to hear it. Oh and...”
He leaned down and whispered,
“Don't tell anyone about my boyfriend, ok? I've got a reputation to uphold here.”
“Your secret's safe with me.” Dwight giggled
“Good to hear it.”
Mr. Kaysen nudged Dwight forward,
“Now off you go. It's time for you kids to go home and let us teachers rest.”
“Sure thing.” Just as Dwight was about to walk out, he turned once more and said “And thank you again...”