A big thank you to Mimi77 for the prompt about Fletcher's first date. I hope you all like it :)

"Dad? Pop?" Claire called out as she opened the door to her family's apartment to find it empty. Detouring past her parent's apartment on her way home to her own place, Claire wanted to show Blaine and Kurt the new pieces she'd been working on.

Claire, now 23, was a graduate from Yale University after majoring in Art and topping her class. Her whole childhood was spent with a pencil or a paintbrush in her hand and so the young brunette put her passion into a career.

Only out of college a year, Claire was still working toward her dream of owning her own boutique art gallery somewhere in New York where she had the freedom to create whatever she liked all day every day. For now, she worked at the Museum of Modern Art restoring some of the greatest artworks in the history of modern art. She was immersed in the works of Van Gough and Monet all day so she wasn't complaining.

The 23 year old lived on the lower east side with boyfriend of three years Christian but came home as often as she could. She moved back to New York after graduation to be closer to her family because four years in New Haven without them was torture. She even missed Fletcher who was as annoying as ever but that came with the territory of being a thirteen year old boy.

"They're not here" Fletcher chuckled as he emerged from the kitchen with a soda in his hands "They went to that Italian place on West 13th that they've loved for like ever to get take out. They said they'd be about an hour, half an hour ago. You know what Papa is like when he has to chose what to eat from there" the teenager laughed

"And they left you here alone?"

"Hannah down the hall comes in every ten minutes with an excuse about needing to borrow something just so she can check on me. Dad's request no doubt"

"No doubt" Claire smiled and pulled her little brother into a gentle hug as he closed the distance between them. She couldn't believe he was growing up so much, in maturity and height. He was nearly the same height as his sister already "How's school, kid?"

"Alright, I got promoted to lead pianist in the band"

"Nice work. All those piano lessons with Dad are paying off"

"Didn't he try to teach you to play too?" Fletcher asked as he made his way through to the living room and flopped down on the couch. He crossed his ankles as he put his feet up on the coffee table only to have them slapped down by Claire as she joined him on the couch.

"I was a lost cause when it came to the piano. My shining moment was playing one note at the end of a song at Dad and Papa's wedding. I never progressed from there" she chuckled "He taught me to play the guitar instead"

"Like that's any easier..."

"You're right, it's probably not. It was either master the guitar or take singing lessons from Papa... I don't sing"

"You could sing in high school"

"I don't sing now"

"Papa laid off trying to teach me to sing when my voice broke" Fletcher laughed thankfully. They both loved Kurt and were amazed by his singing ability but neither could live up to his talent. He was a Broadway star and they were lucky to hold the tune of Silent Night at Christmas.

Fiddling with the ring on the top of his soda can, Fletcher looked up at his sister wanting to ask her something important. He loved when Claire came home to see them especially now she was back in New York but the 13 year old never got to talk to his sister alone.

"Spit it out Fletch"

"Spit what out?"

"Whatever you want to ask" Claire chuckled. She could read her brother like a book which always played to her advantage over the years. She always knew when he was lying about something or just really needed to talk.

"How do you..."

"I'm your sister, I'm meant to know when you need me. It's a gift"

"It's creepy but I did want to talk to you about something" Fletcher sighed and set his soda down on the coffee table before crossing his legs and facing Claire "It's about a girl"

"Ooh my baby brother has his first crush" Claire gushed and was met by a heavy sigh from her brother "Come on, you knew I'd react like this"

"Beats how Dad or Papa might react..."

"You haven't told them?"

"And I don't intend to tell them but I might have to because I want to ask this girl out on a date. I know she likes me too" Fletcher continued bracing himself for the high pitched squeals that are no doubt going to come from his sister "Please don't squeal"

"Why would I squeal?" she laughed bouncing excitedly in her seat. This was such a big moment for her brother; she couldn't help but be excited

"Because you're my sister and I know you"

"I resent that but I'll let it pass. You will need to tell them though, they're not going to let you guys go out on a date without a chaperone"

"That's exactly why I don't want to tell them" he sighed and collapsed back on the couch "They'll want to sit next to us if we went to a movie or Papa will want to take photos all night"

"Been there" Claire laughed and patted her brother's knee gently remembering back to her first date.

Going to a movie with her first ever boyfriend Ben, Claire had to endure Kurt acting like it was her Senior Prom taking photos from every angle in a million different poses. It didn't help that Blaine and Kurt sat right behind them in the movie and coughed every time Ben tried to put his arm around her shoulders.

"I have a proposition for you Fletcher James Anderson-Hummel" Claire smirked and pulled her brother from the foetal position he'd curled himself into out of anxiety. "You have to tell Dad and Papa about this date but instead of them embarrassing you all night, how about if Christian and I chaperone?"

"You want to come with me on my date?" Fletcher asked in disbelief that his sister would want to double date with two teenagers. He never considered the benefits of Claire going with him rather than his parents.

"Well you have to ask this girl out first, whose name you still haven't told me..."

"Penny Davis"

"Aw..."

"Claire!" Fletcher sighed "Maybe I shouldn't have told you anything" he snapped and got up off the couch and stormed off to the kitchen.

"Hey!" Claire growled and immediate followed him "I'm sorry but I'm just a little excited that you could be going on your first date. I'm a big sister; this is a proud moment for me"

Sitting down on the stool by the bench, Claire gestured for Fletcher to sit beside her. The thirteen year old climbed onto the chair and rested his head down on the bench.

"Sorry, I'm just nervous. I've never done this before"

"Why don't you call her and just ask if she'd like to go to a movie with you then we can start freaking out ok?"

"Call her?"

"Yeah, with a phone?" Claire chuckled nudging her brother gently "It might be easier doing it now while Dad and Papa are still out"

"What would I even say?"

"Hi Penny, it's Fletcher. I was wondering if you'd like to go see a movie with me on Saturday afternoon. Then you wait for her answer"

"That's it? That's all I have to say?"

"Simple as that" she smiled and took the phone off the charger handing it to her brother "You never know if you don't ask"

Fletcher nodded nervously and took the phone. Keying Penny's number into the phone, the teenager fidgeted nervously on the stool waiting for someone to answer. Claire could tell someone had answered when her brother froze. Terrified, it took him a few seconds to snap back to reality and just say hi to the girl he liked.

Saying the sentence Claire had suggested, Fletcher managed to ask Penny out on a date only stuttering once. So far so good. When Penny stepped away to ask her Mom if it was ok to go out that Saturday afternoon, Fletcher's knee started to shake again and even a calming hand rubbing his back didn't help.

"Penny's Mom wants to talk to Dad or Papa" Fletcher gasped once Penny had returned and said that it was ok. Covering the mouth piece of the phone with a shaky hand, he never thought Mrs Davis would want to talk to his parents.

"Give me the phone" Claire chuckled and almost had to pry the phone from the death grip Fletcher had it.

Explaining that Kurt and Blaine weren't home at that moment but they would be soon, Mrs Davis was more than happy for Claire to chaperone. Friends with Kurt through the PTA at school, she had heard many good things about Claire and her endeavours to conquer the art world. Penny's Mom just wanted to ensure that the kids would be with an adult the whole time and understood that both her daughter and Fletcher might be more comfortable with Claire and her partner rather than a parent.

Claire was rather surprised at how easy the whole situation was. Of course she promised Mrs Davis that her father's would know about this date, at what time and where in case something was to happen but that was standard parental worry Claire expected.

"You my handsome baby brother are going on your first date on Saturday afternoon" Claire beamed after she'd hung up the phone. By the anxious expression on her brother's face, Claire seemed more excited than he did "Are you excited?"

"Uh... uhm yeah but kinda scared at the same time if that makes sense"

"There's nothing to be scared of Fletch..." Claire began but her sentence was cut short by the sound of keys in the lock of the front door "You ready to tell Dad and Papa?"

"No..." the teenager sighed praying Claire would stay quiet. He knew that was never going to happen though

"Tough" she smirked

XXXXX

"Is it sad that I'm actually pumped to chaperone this little date today?" Christian laughed as he and Claire stepped into the elevator of her parents' building.

"Yeah, a little" she chuckled and nudged her boyfriend gently "But I'm excited too, I'm glad I could do this for Fletcher. We've never really done the whole 'normal sibling' thing because there's such a big age gap between us"

"You're not missing much, believe me" he smiled. Christian grew up with a fraternal twin sister and two older brothers who were close to his age. Their relationship was the epitome of 'normal siblings'. They hated on each other, played pranks but loved each other all the same. They were all too close in age to do something like this for each other. Christian's fondest memories of his first date were the constant teasing from his older brothers about his choice of clothes or whether the girl would kiss him or not.

"Normal in any sense is a foreign concept in my family..."

"Your Dads are not that bad"

"You haven't seen anything yet..."

Claire opened the door to her family's home and was not surprised at the sight in front of them. Blaine was on the couch half watching the Yankees game half watching the door to his son's bedroom, while Kurt paced frantically back and forth. Both looked like nervous wrecks.

"Are they ok?" Christian whispered as he noticed Claire's parents' behaviour.

"Are you sure you want to be a part of this family?" Claire chuckled and nudged Christian toward Blaine who seemed a little calmer than Kurt. Making her way over to her Papa, Claire pulled him into a gentle hug "Are you ok?"

"I don't think I was this nervous when it was your first date..."

"That was 10 years ago, Papa"

"I know and you're my little girl" Kurt sighed and pressed a kiss to his daughter's temple "But he's been getting ready for an hour..."

Claire had to hold back her laugh as Kurt started to pace again. Knocking on her brother's door, Claire heard frantic shuffling on the other side "Come on Fletch, you take longer to get ready than I do"

"And she takes forever" Christian called out from the couch. Shooting her boyfriend a 'you'll keep' glare, she laughed as he slumped back into the couch without another word.

"Can't be as long as Kurt" Blaine chuckled softly.

"I heard that!" Kurt snapped mid pace. Blaine too slumped into the couch beside Christian knowing they'd both be sleeping on the couch if they said anything else.

"Come on Fletch!"

"Claire? Help me!"

Exchanging a look with Kurt, Claire opened her brother's door and disappeared inside before Kurt could join her. She could imagine how anxious Fletcher was about this date and wanted to help. Looking around his bedroom, Claire looked at clothes strewn everywhere. It looked like he'd emptied his closet out onto the floor of his room.

"How do I look?" the nervous teen asked as he pointed to his outfit. Dressed in a pair of nice skinny jeans, an untucked tailored white button up shirt, a tie and his tux jacket, all he was missing was his shoes "I'm hot in this though. I don't know what to wear. Help"

"Take off the suit jacket, loosen the tie, roll up the sleeves of your shirt and put on your black converse sneakers"

"But..."

"Trust me"

Fletcher did as his sister said and even let her fix his hair a little before he stepped in front of the mirror.

"I look cool..."

"You underestimate my artistic talent and knowledge of what teenage girls like. Penny will think you're the cool musician. Every girl loves one of those, I should know" Claire chuckled. A math geek and stock broker on Wall Street, Christian was a keen musician in his spare time. Playing gigs at a bar close to their building, he let all his frustrations from the Stock Exchange out in his music. Claire fell in love with his music when they met in sophomore year of college.

"Awesome"

"Are you ready? If we don't leave now we'll be late"

"Ok" he nodded with a weak smile "I'm scared I'm going to stuff this up"

"You're going to be fine, Fletch. You've got Dad's charm, you just have to say hi and she's head over heels for you"

"Now you're just making that up..."

Kneeling down facing her brother, Claire took Fletcher's hands gently. Blood related or not, that boy was the closest thing she would ever know to a brother and he was probably the best little brother she could have asked for. It was amazing to see how he'd grown into such a mature young man but she needed to instil a little bit more confidence into her brother's head.

"You are an awesome kid, Fletch. You're smart, handsome and such a little charmer. You've just gotta be yourself today and Penny will love you. She'd be stupid not to"

Launching himself into his sister's arms, Fletcher nearly bowled her over with his hug. Squeezing his arms around her shoulders, he kissed her cheek gently "I'm so glad you're coming with me today, C. I love you"

"I love you too, little bro"

The siblings pulled away from each other as they heard a collective 'aw' from the other side of the door. Smirking to one another, Fletcher and Claire snuck to the door and opened it to find Kurt, Blaine and Christian all with their ears pressed against the door.

"You're all as bad as each other" Claire laughed as the three men tried to act like they weren't just eavesdropping on the conversation "Now if you three will excuse us, we have a date to get to"

After letting Kurt take only a few photos, Claire pushed both Fletcher and Christian out the door before Blaine could start a lecture about what to do on the date. Fletcher was already nervous without them adding to it.

Picking up Penny on their way to the movies, everyone was thankful it was only a short journey. Both Claire and Christian hoped the young couple they were accompanying would relax. They walked rigidly next to each other into the theatre not really knowing how to act around or talk to each other.

"Christian and I are just going to sit up further. You guys stay here" Claire smiled as Fletcher and Penny found a couple free seats. Seeing two seats a few rows back, Claire could still keep an eye on her brother without sitting next to him.

"You aren't sitting with us?" Penny asked a little taken back. She wasn't used to laid back parents or siblings in this case. She expected Claire to sit right next to them.

"We'll meet you right here when the movie is over"

Claire and Christian climbed the few extra stairs to their seats as Fletcher and Penny took their own. The young pair still sat silently next to each other fidgeting with the Red Vines packet they had bought to share.

"You... You uh... look really pretty today Penny" Fletcher smiled "I like the braid in your hair"

"Thanks, my Mom did it for me. I still can work out how to do it in my own hair"

"I've watched my sister braid her own hair and it doesn't look easy. I swear she nearly dislocated her shoulder doing it once"

"Yeah it's an art" Penny giggled and took a sip of her soda "I'd love to be able to braid my hair like Mrs Carolina"

"I'm too busy trying to understand her homework to notice her hair" Fletcher laughed. In just about every class together at school, he knew Penny would understand how hard Mrs Carolina's geography class was even though she was the smartest girl in their grade.

"I know! This week's worksheet is just confusing. How are we supposed to know the capital of Laos and everything about that country if she won't let us use our textbooks?"

"That's the beauty of homework, what Mrs Carolina doesn't know won't hurt her"

"Fletcher!" the teenage girl gasped "That's genius!"

The young pair settled comfortably with each other as the previews for the movie started. Peering back at his sister, Fletcher caught Christian's attention who dramatically yawned and gently placed his arm around Claire's shoulders. Nodding, he wanted Fletcher to try the very cliché move. The thirteen year old bit his lip as he yawned, not quite as dramatically as Christian and rested his arm around Penny's shoulder. His teenage heart skipped a beat as she snuggled closer to his side and rested her head on his shoulder.

"Oh my god" Claire whispered as she elbowed her boyfriend hard "You're teaching my baby brother bad habits"

"It got the girl to lean on him and it's not a bad habit, it works on you every time"

"It does not!"

"Every time"

Claire soon gave in and snuggled close to Christian as the movie started. The family-comedy wasn't really their type of movie but it was suitable for the two teenage love birds. Keeping a close eye on her little brother throughout the movie, she was proud that his hand didn't move from Penny's shoulder to anywhere inappropriate like most teenage boys would. He was being the gentleman Kurt and Blaine had raised him to be.

When the movie finished, the teenagers didn't really want to get up. They were comfortable and happy there together. Descending the stairs to meet them, Claire suggested they detoured past the gelato shop on their way back to Penny's building. She wanted to give the young couple a little more time together before they had to part ways.

Just as Claire hoped, Fletcher and Penny didn't stop talking all the way to the gelato shop, while they ate and the entire journey back to Penny's home. The conversation that was non-existent earlier that day was flowing freely now. Just as they got back to the young girl's building Christian held Claire back a little letting Fletcher walk Penny to the door alone.

"What are you..."

"Shh" he laughed and pointed to the young couple who were standing together on the stoop holding hands "I'm giving your brother his first kiss"

They watched on as the pair talked a little more before Fletcher finally closed the gap between them and pressed his lips to Penny's gently. It was short, sweet and perfect for a first kiss. Saying goodbye to her one last time, Fletcher almost skipped back to his sister with a smile on his face no tragedy could erase.

"Best date ever"

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