ariamiipenguu requested a part 2 to the last Ian imagine, Your Brother! also this art is by her too!

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"Barley!"

Ian leaned back, sighing heavily. The moment had been ruined. All of his confidence collapsed around him as he felt the tone in the room go from completely warm and perfect to awkward and heavy. He tried not to get too annoyed. His overbearing older brother hadn't meant to ruin his first chance to really tell you how he felt and express it... right?

Whatever. It didn't matter. It was over with.

You observed your friend as he leaned back against the back of the couch. He covered his face with his hands and remained still. 

"Ian, what's wrong?" you asked. You couldn't hide the fact that you were disappointed. You had really been hoping that he would kiss you in that moment. 

He sat up, his arm draped over the top of the sofa. As he spoke, his free hand moved wildly. You could see how his hand shook. "I-I really just wanted this night to go perfect, you know? I feel like every single thing that could have gone wrong has gone wrong. It's just frustrating. I am really sorry, ___."

"What are you apologizing to me for?" you asked with a giggle. "Ian, there's nothing wrong with how tonight is going. You don't have to be embarrassed or worry that I'm embarrassed that your brother really wants us to get together. Barley is hilarious. And you are awesome, and I'm really waiting for the moment you decided enough is enough and kiss me."

His eyes widened. "Are you seriously?"

You nodded. 

"O-Okay." He sat up and scooted forward. 

In the back of his mind, he remembered Barley's advice from two weeks prior. 

"So you like this girl, right?"

He sighed, shrinking down further in the passenger seat of his brother's van. "Yeah..."

"Then listen close," he said. "Are you listening?"

"I'm listening." He wasn't so sure about what he was about to hear, though. 

"You might want to take notes. I'm about to give you some good stuff. Okay, first of all, just know this. The first kiss is bound to be awkward, so just roll with it. You don't know what you're doing, and that's fine, because chances are, she doesn't either."

"Really?"

"Uh-huh. Just reach out and touch her cheek. Not too much. Just a little. And put your other hand on her waist, and then lean in. Tilt your head a little --- and I mean a little, Ian. You hear me? A little. And then you kiss her. Do it gently and don't open your mouth. Have you ever seen those videos where those people meet for the first time and they've never kissed a girl before and they kiss her and she doesn't do anything because they've, like, bit her lip off or something? Ha! Classic. Don't do that, little brother. Don't do that."

"Wow," Ian said, nodding. "That was actually really good advice. I didn't know you'd kissed anyone before."

"Oh," he chortled, shaking his head and waving his hand. "I haven't. But I'm not an idiot. Oh, hey, it's eight now. You'd better get to class. I'll pick you up at three! And don't forget, tilt a little bit!" 

Miraculously, remembering this bit of useful advice given to him was really making Ian feel slightly okay with what he was about to attempt. This was his very first kiss, and he didn't want to make it embarrassing. He didn't want to disappoint you either; he liked you so much.

Okay, Ian thought. Just reach out and touch her cheek gently. 

He did. 

Now lean in and tilt your head only a little...

He did. 

Great! You've got this now. You're almost there. 

Is this supposed to be this hard?

His other hand found your waist, Your hand was there, and you took his in your own. Okay, Barley didn't tell me that might happen. Suddenly, his palms were sweaty. Oh, gross! 

Just lean in, Ian! Just lean in!

He did. Except he pushed his head forward too hard, and your eyes opened wide in shock as his lips collided with yours. He pushed his lips out, suddenly terrified of being one of those guys that embarrassed themselves in those videos. 

Your eyes fluttered shut and you tilted your head and kissed him. You moved your lips softly, and slowly, he realized how to start moving his, too. He felt himself calm down and he gripped your hand confidently now. 

When you pulled away, your eyelids opened slowly. Ian's were half-closed as he leaned back and hummed. You laughed softly. 

"Was that too awkward?" he asked. 

"It was a little awkward," you admitted.

His face fell. "Great. Here I was thinking that it was pretty good."

"Ian," you said, grabbing his hand. "I didn't say it was bad, you dummy."

"But it was awkward," he said. 

"Yeah, but I like you because you're awkward. It's cute. You don't need to ever think that I'm going to be embarrassed of you." You smiled. "Plus, if you ask me out, we can practice the kissing thing more." 

His eyes opened wide. "O-Okay. Would you... uh, would you... out with me? I mean go. Go out. With. Me." He swallowed hard. "Please?"

You laughed again. "Yeah, I'll go out with you." 

"Great," he sighed with relief. "I'm sorry."

"Stop apologizing." You put your hands on other side of his face and pulled him close. You kissed him softly, pulling him close to you as his hands went around you and he hugged your waist loosely. 

"Aw, yeah, I knew it had gotten a little too quiet down here. You two are just kissing in the dark like I knew you would be. When did you grow up so fast, little Iandore?" 

You dropped your head and snickered quietly as all of the happiness in Ian's face completely drained. His brother, who was standing at the top of the stairs, peeked down with a look of complete pride.

"Barley!" Ian cried. "Are you kidding me!?"

"Wait 'til I tell Mom! She'll be so proud, too!"

It just got worse for Ian.

"No, don't tell Mom!"

/ / /

double update today! check back later for a barley imagine :-)