Combining a few prompts here. One of my most commonly asked questions is: Does Stefan date? How does he feel about not being able to date anymore? So, this delves into all that!

kimkey prompted " if Stefan saved Elena like in canon, maybe Damon's reaction when he learns of the event? I mean he just found out his Little not Caregiver brother was out, at night, alone and jumped in a river to save a drowning family. This event alone is pretty much fuel as why Damon thinks Stefan shouldn't date or be alone." + atmenza1 (when discussing Stefan dating) prompted "Could be a good argument though. Perhaps a sneak about, but then something upsetting does happen to Stefan and he realizes Day was right."

This chapter takes place before Tanner got his cumpence.

"When was your first kiss?"

It's an innocent enough question. Stefan and Elena sit crisscross-applesauce on the Wickery Bridge one quiet Friday afternoon. She's looking at him with great curiosity.

"I mean, do you even remember?"

Stefan chuckles. "Of course I do."

"Really? How does that work?"

"The kiss? Or…"

She rolls her eyes. "Remembering everything. My dad is over a thousand years old and it's insane the things he does. I mean, don't people usually forget with age?"

"We don't grow older, though. Our minds just absorb everything." Stefan shrugs. "You think you don't, but then it comes to you like that." He snaps his fingers. "I wish I didn't have some of the useless trivia in my head."

"It makes for a fun History class, though."

"That it does."

"So." Elena sits up straight. "First kiss."

Stefan smiles a little. "I was 13. My tutor began bringing his daughter to train her in the trade. We were left alone one afternoon, got talking about books. It was quick. Never saw her again."

"Did anyone ever find out?"

"Damon. He teased me for about a month."

Elena giggles. Stefan regards her for a moment, gnawing on his lip.

"You?"

"Oh, uh. Matt. Spin the bottle, long before we started dating. Looking back, wasn't that great but at the time I felt on top of the world."

Stefan takes in her dreamy smile and can't help but match it. "Do you miss dating him? I mean, is it weird just being friends?"

"It was in the beginning but I'm okay with it now." She sighs, picking at a loose string on her shirt. "We would've had to break up anyway after I got adopted."

Stefan's face drops. "Right."

"It's weird, there hasn't really been anyone I've wanted to go out with. I was so preoccupied with my parents dying, then being stuck with Alaric." Elena shifts uncomfortably. "But it's the fact that I can't now that sucks."

"I hear you on that one."

"You and those girls from the party…you didn't…"

Stefan shakes his head. "No. Damon showed up before anything could."

"I'd like the option, you know?"

"In time, I'm sure your space will sort itself out and you'll be able to balance it well enough."

"What if it doesn't?"

Stefan hates the pitiful look in her eyes. Every time they come to this bridge, she gets sad. He's debated not taking her here at all, but she insists. The two sit and talk about everything, anything, sometimes nothing at all. That night bonded the two forever. Sure, there was a point where he debated started something with her but he wasn't sure if that was his love for Katherine talking. Now, he knows they're better off as friends. Neither have any business in a romantic relationship right now.

Still, he inches closer and caresses her cheek with his thumb. Elena looks up at him with her wide brown eyes, mouth slightly agape.

"Stefan, I don't…I mean…you're my friend," she whispers.

"I know. But who knows when we'll get to kiss anyone again? What could it hurt?"

Elena nods and scoots over. Their faces are just inches apart. Stefan leans in, his lips brushing against hers. She deepens the kiss, sliding her arm around his waist. He's reaches to pull her onto his lap…

His stomach hurts.

Stefan tries to ignore it. Elena's tongue enters his mouth and brushes against his own.

"Ow," he mumbles.

Elena fumbles back a little. "Did I bite you?"

Stefan shakes his head and pulls away completely. "I…I don't feel so good."

Elena frowns, taking him in. "Are you slipping?"

"N…no?" He folds his arms over his chest. "I mean, not yet. I just feel weird."

"Let's head back to The Grill."

It's where they're supposed to be, if her parents or his brother ask anyway. They were supposed to meet up with Bonnie and Matt. Klaus and Caroline don't want her anywhere near this bridge if possible. Damon would have a fit if he knew he was alone with a girl, no caregiver present.

Stefan pulls himself up and they begin the walk back to The Grill. With each step, he's looking around. Anxiety bubbles in his stomach. The sun still shines, but they're alone in these woods. Anything could pop out.

Snap

Stefan jumps. "What was that?!"

"I stepped on a twig." Elena puts a hand on his shoulder. "It's alright, Stef. We're just 10 minutes out."

Stefan nods, trying to pick up the pace. His vamping isn't working as well, which only points to him slipping.

No. No. Not without Damon. You are not going to scare Elena like that.

They turn a corner and he spots the clearing in the distance. Just another few minutes and they'll be out. Longer to The Grill, but the end is in sight. With each step, Stefan attempts to build his confidence and big space.

You want to hang out with your friends. You want to play pool and just be a normal kid.

You want Damon.

Stefan bites his lip to hide a whine. He fidgets, looking around.

"Are we going the right way?"

"Yeah." Elena points out the clearing he just spotted. "Not long now."

"O…okay."

Elena stops, touching his hand. "Do you want me to call Damon?"

"I…I'm fine."

"Stef…"

"I'm fine, Elena, let's just keep walking. Bonnie and Matt are probably waiting on us."

A familiar voice comes from behind them. "They are."

The teens whip around. Damon towers above them both, arms folded over his chest. Stefan swallows in spite of the relief taking over his tummy. It takes all he has to not fall right in his big brother's arms. Damon is here to save the day! Why can't he let himself be happy about that?

Damon continues before either can speak. "They were worried when neither of you showed up. So, they called us."

Elena raises a brow. "Us?"

Klaus vamps to his side. She ducks her head. Stefan keeps his eyes locked on his big brother. He doesn't want to leave Elena if she needs him, but he also just wants to go home.

"What were the two of you thinking?" Klaus asks, hands on his hips. "Wandering through the woods?"

"We weren't wandering the woods, Daddy," Elena whispers. He narrows his eyes. "We were using them as a shortcut…to get to and from the bridge."

Klaus' eyes widen. Elena is quick to defend herself but Stefan remains quiet. Damon's face turns puzzled from the argument but snaps out of it.

"I'll leave you to handle that one," he says to the father. His eyes flicker back to his baby brother. "Let's go."

Stefan obediently follows him out of the woods, not even caring when Damon takes his hand. He slides into the backseat of the Camaro and fumbles with his seatbelt. Damon stands in the doorway, a frown on his face.

"Need some help?"

"I…I can do it."

Damon reaches over and grabs the belt, securing it into place. Stefan's cheeks tint pink. Damon shakes his head and gets up front, pulling away from the clearing at once. In the background, Stefan can hear Elena and her father fighting. He hates that she's in trouble. Maybe he could tell Klaus it was his idea? Okay, that's a lie, but he didn't talk her out of it. He's the vampire, supposed to be the more mature of the two. Stefan shouldn't allow Elena to do anything dangerous.

Who is he kidding? Elena would never let him stop her from anything.

The ride home is short and silent. Stefan keeps his eyes trained on Damon, trying to read his face. His brother doesn't make it easy. There's no telling what he's getting into once they get home.

Nothing is said until they're safely inside the living room. Stefan sits on the couch while Damon stands before him, licking his lips.

"Why the bridge?"

"Elena wanted to talk."

"And you can't do that at The Grill?"

"It's different. She didn't want a ton of people around. The bridge…it's…it's sort of our spot."

Damon raises a brow and Stefan instantly curses himself. His younger side is almost always honest. He craves for Damon to fix every problem that comes their way. Stefan currently balances between the two halves, not ready to drop completely.

"What do you mean your spot? Stefan, do not tell me you two are…"

"No! We're not!"

"Because we've discussed this. You are still adjusting to your space, you could drop at any point. You aren't ready to date."

"I know," Stefan whines, his cheeks turning pink once more. "We aren't doing anything like that. Elena's just a friend."

"Then what is so special about this bridge? I know it's where her parents died but what does that have to do with you?"

Stefan rubs the back of his neck. He tries to think up a lie, anything his brother might believe. As he looks back up at Damon, he knows nothing is going to make him stop unless it's the truth.

"I um…I was there that night."

Damon blinks, registering the information. "What?"

"Of the accident. It was before you came to town," Stefan speaks quickly, his words practically jumbling together. "It was late, I was taking a walk to try to avoid, well…" He bites his lip. "I heard the car swerve. By the time I got there, it was already in the water. I jumped into save them."

Damon drops beside him, his eyes wide and mouth open. Stefan takes a deep breath before continuing.

"M...Miranda was already dead," he whispers. "I went to save Gr…Grayson bu…but…" His lips tremble. "He told me to save Elena first. So, I did. I pulled her from her seatbelt and dragged her to the surface."

It was only then he saw her clearly for the first time. How much she looked like Katherine. He heard about the doppelgänger but this was up close. Her eyes closed and still, the long brown hair. Same adorable nose and pale cheeks. She was alive. Not just undead, but truly alive.

Stefan stared at her too long. Maybe if he hadn't, he could've gotten back down there sooner.

"I went back for him, but it was too late," Stefan whispers. "All I could do was phone the police. Said I watched some Good Samaritan pull Elena from the car."

Damon slowly nods. "You saved her."

"I…I could've done more. If I wasn't on animal blood, if I could drink human…if I hadn't spent so long staring at her…"

Stefan's voice breaks and tears gather in his eyes. He knows now that Miranda and Grayson weren't great parents. They never truly accepted Elena for who she was. But they were still people, deserving of a life. It wasn't up to him to play God. And if he had been quicker that night, at least Grayson would still be here. So many maybes, what ifs. He could've turned things around…

His thoughts are cut off by Damon smacking him on the shoulder. Stefan looks up at him with wide eyes. Damon has his "serious big brother" face on.

"Don't you dare start that," he growls. "Do not start your self-loathing. You did everything you could."

"You weren't there," Stefan whispers, weakly. "You don't know that."

"I know you, Stefan. You play hero, even to your own detriment. That night, you did all you could to save that family. And you did."

"One of three."

Damon shakes his head. "You said it yourself, Miranda died on impact."

"If I had gotten there before it went off the bridge…"

"You couldn't have known it would happen before it did."

"Still." Stefan blinks away the tears. "I could've gotten back to Grayson sooner. I was just…she looks so much like Katherine…I hadn't really seen her before and I…I don't know…"

"You were in shock. It happens. Besides, there's no way Grayson could've stayed alive long enough even if you did come right back."

"You…you don't know…"

The tears spill down his cheeks.

"I know she's happy with Klaus and Caroline," Stefan's voice is broken. "But…it shouldn't have happened. She's so sad sometimes."

Damon tilts his head. "That's not on you to fix, buddy."

"Day…"

"No." Damon takes his baby brother's face into his hands. Stefan practically melts into the embrace. "I may not have been there that night, but like I said, I know you. Stefan, you were a hero that night. You saved a life. Because of you, Elena is still here." His stern yet loving and protective eyes remained locked on Stefan's sorrowful ones. "You did good, baby boy. Do not let the voices in your head tell you differently."

Stefan collapses against him. Damon quickly pulls him onto his lap and curls him into his chest. He gently rocks him. Stefan buries his head in his shoulder, the tears falling fast.

"This is why I don't want you dating," Damon whispers. "You did the right thing that night, Stefan, but I see what this does to you. Your instinct is to play hero and you can't. The aftermath stays with you."

Stefan sniffles and clings tighter. He thinks about all the times he wanted to join up when Damon fought in the war. It would've been easy to lie about his name so he could enlist. Damon forbade him. He knew exactly what all the bloodshed would do to him. Nothing could stop him from joining up in World War II and Damon was right. He still has nightmares from that time in his life.

"No more playing hero," Damon instructs. Stefan nods into his shoulder. "I'm serious, Stef. You can't keep doing this to yourself."

"I…I know, DayDay," he whimpers.

Damon lets out a long sigh and keeps him close. Stefan slides his thumb into his mouth and shuts his eyes. The big boy thoughts aren't completely gone, but Damon will protect him from them.