Requested by multiple users after I made up a headcanon and posted about it on my message board.

Female reader.

~~~

Spot Conlon was a man known for his somewhat cold exterior, and for leading the fearless Brooklyn newsies.

Not for braiding hair.

(Well, it was bound to rub off on him sometime. He had an older sister growing up, so it wasn't surprising if he picked up some tips.)

~~~

I twisted my hair together, braiding it quickly and skillfully. I would always braid my hair and put it up inside my cap, never cutting my hair shorter than shoulder length. But since I valued sleep and always woke up at the last minute, my braids were usually a tad bit messy.  My hair was one of the only things that reminded me of my late mother, which is why I didn't cut the majority of it off.

"Hey, you're up early." my boyfriend, Spot, remarked as he came out of the bathroom. He was typically the first one up, with me following him to help him wake up the other newsies before getting our papes.

"I wanted to have more time to make my braid neater." I replied, shrugging. "Today feels like a good day."

Spot laughed, turning me to face my right before sitting behind me and taking my braid out. "Here, I wanna do it." 

He began coming his hands through my hair before gently braiding it, using a small red ribbon to tie a knot at the end of the braid. He curled it up onto my head before putting his own newsie cap on my head.

"Have fun sellin' today!" Spot cheered before running out to wake up everyone else.

I smiled and shook my head, surprised at how Spot knew how to braid hair.

~~~

"Spot, can you braid my hair again?" I asked him.

Spot looked up from his book, his face a mix of happiness and uncertainty. "Sure."

I sat down by Spot, and again, his hands moved skillfully, putting my hair into a braid a second time.

"You should leave your hair in just a braid more. You look prettier." Spot remarked before I left the room. I turned back to him, surprised.

"Oh. Okay." 

~~~

"(Y/N), can I braid your hair?" Spot asked as he sat on some crates by the dock, watching his newsies horse around in the harbor.

I turned to him as best I could in my position leaning against him, my face an expression of suspicion. "Why?"

Spot shrugged. "I feel like it."

I sighed, a small smile on my face and taking off my hat for Spot. I turned to face the harbor, and Spot began unraveling my current braid and re-braiding my hair. 

"Your hair is so soft." he muttered.

When he finished, he pressed a kiss to the top of my head. "I love you."

I leaned my head back and reached a hand up to the back of his neck, pulling him down for a kiss. 

"I hope you're going to keep wanting to put up with braiding my hair, by the way." I said as he hopped down from his seat to settle a small fist fight between two newsies a few feet away. He laughed and winked at me, tipping his hat. "Be right back."

"I hope you're going to keep wanting to put up with me wanting to braid your hair, by the way." he shot back with a smirk.

I rolled my eyes and blew him a kiss. "Love you."

This turned out a bit different than what I expected it to, I guess. But I still liked it in a way. 

Hope this was enjoyable, and shoutout to all the people who liked and encouraged me to write my headcanon!