chuck blair henry


There are people who care so deeply about you, if you would just let them.” — Lily Van der Woodsen 

List of head canons for the bass family

aka cute shit i can imagine chuck, blair, and henry doing from gossip girl

-henry not letting anyone tie his tie’s except chuck until henry is old enough for chuck to teach him how to do it himself, but even then he still prefers chuck to do it for him

-henry and blair going to the park to feed the ducks, sometimes with dorota, sometimes just the two of them

-both chuck and blair alternating reading to henry before bed every night

-after chuck is done reading the spectator in the mornings, he gives it to henry to look at the comics and do the crossword puzzles that nate makes sure to put in every day just for him

-speaking of nate, he babysits a lot as do serena and dan

-nate takes henry to a basketball game and other sporting events

-blair, serena, and jenny putting on a pre-fashion show for henry to show off blair’s new lines for waldorf designs and getting his opinions and such

-henry modeling some of the boys clothes that blair designed which were inspired by him, even goofing around and modeling the girls clothes during the fashion shows bc fuck gender roles

-henry helping blair make her famous pumpkin pie for thanksgiving and baking holiday treats

-family trips to paris

-chuck giving henry his signature scarf which he wears everywhere but after a while he starts getting bullied for it. it starts as light teasing and shoving in the hallways at school but comes to physical fighting in the park one day and henry runs into his daddy’s arms crying and he and blair have to comfort their baby and have a menacing civilized talk with the bully’s parents

-henry scheming and bribing his way through minor situations in his life, although not nearly as bad as his parents (as stated by josh schwartz since henry would have a happy childhood and wouldn’t have the emotional instability and challenges that his parents faced)

-henry accompanying chuck on his daily walks with monkey

-henry spending the weekend at eleanor and cyrus’s or lily and william’s so chuck and blair can have some alone time if u catch my drift ;)))

-harold, roman, and blair taking henry ice skating during the winter

-chuck and blair bribing henry with cookies or ice cream or whatever to be on each of their sides when they’re betting on something or having an little argument/disagreement

-also chuck and blair making a bet on what henry’s first word will be (((they both lost)))

-yall know blair cried on henry’s first day of school and although chuck will NEVER admit it, he def got a little choked up when they dropped henry off

-blair being a boss at the school PTA meetings and taking control, planning everything from bake sale fundraisers to the schedule for snack time

-the basses having a family photoshoot every year which is displayed proudly in their townhouse like how chuck had that picture of him and blair in his penthouse at the empire (i know that was from a promo pic in real life, but it had to have been professionally done in gg world in order for it to be on chuck’s shelf so don’t tell me they wouldn’t have another photo sesh with their son)

-chuck teaching henry to play squash

-blair and henry watching all of her favorite movies together (breakfast at tiffany’s, roman holiday, etc)

-all of them matching or complimenting each other’s outfits in some way whenever they go to events/galas/charity balls together (i.e the boy’s bow ties matching blair’s dress, etc)

-when chuck is away on business and it thunderstorms at night, henry sneaks into his parents room and wakes blair up and says “i was checking to see if you needed any protection from the storm, ya know since dad’s not here” bc he doesn’t want blair to know he’s scared but henry jumps right then when thunder cracks and blair just smiles knowingly and lets him in to snuggle against her

-chuck not pressuring henry to take over bass industries or go into business and letting him know he should do whatever he wants and whatever his heart tells him to do in the future

-henry getting everything he wants for christmas and always having tons of toys unlike chuck when he was a kid fuck you bart :(((

-chuck and blair loving their baby boy more than anything in the world and always showing him the support and encouragement they didn’t receive as children

wow this turned out way longer than expected but idc i love my precious babies so much ok hope u cried as much as i did while writing this bye


Happy Father’s Day everyone! 

Loved this gif set so much.

Rules of Ruling

Chuck crossed the front door of his townhouse and a smile stretched his lips as soon as he stepped into the foyer. He closed his eyes for an instant and inhaled the familiar scent of Blair’s perfume blended together with the one of fresh peonies that always filled the entrance. It was the sound of Henry’s cheerful voice coming from upstairs, however, that gave him the definitive feeling of finally being home; it reached his ears blurred and muffled by distance, but not any less comforting. Though he couldn’t quite catch what his son was saying, Chuck still felt relieved at the thought that he was close and safe.

Impatient to see him, he turned to look at his driver and bodyguard, who had entered the room behind him, carrying his suitcases. “A detour from the usual itinerary will be necessary tomorrow morning,” he said sternly. “I’m taking my son to school; therefore, we’ll have to leave twenty minutes earlier.”

“At a quarter past eight, sir?” the driver asked for a confirm.

Not pleased with the obvious question, Chuck casted an irritated look at him and took the time to hand his briefcase and coat to his valet, who had promptly approached him, before answering. “Sharp,” he specified strictly; then, straightening his suit’s jacket, he added: “It will be all for tonight. You both can go.”

Just as he was about to swirl around and start making his way to the elevator, Chuck heard Henry calling for him. He turned his head and, directing his gaze to the other side of the room, he realized that the kid had shouted ‘daddy’ from the top of the grand staircase and that he was now running towards him with a wide smile spreading across his face.

Smiling as well, Chuck rushed to the bottom of the stairs; he barely had the time to reach it that Henry, standing on the last step, had already stretched his arms to wrap them tightly around his waist.

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gossip girl: next gen || henry & audrey bass

“Mmm,” Audrey sighed as she downed the last bit of her coffee and wiped at the corner of her lips with one thumb. “I adore Dorota, but her coffee tastes like shit.” She got up and tossed the cup, impatiently waving Henry over to follow. “Mom is going to have your head when she finds out that you deigned to buy discounted caffeine from Pete’s.”
“Hm,” Henry chuckled. “What Mom doesn’t know won’t kill her.”
At this, Audrey paused, her black cape coat slung casually around her shoulders. “Are we talking about the same Blair Bass?” She raised her eyebrows as if he should have known better. “She’ll smell it on your breath.” 
excerpt from [X]

(Posted this a few months ago but I 100% have to post this as I’m posting photos from the Gossip Girl finale)

Literally THE best moment of the finale, I just wish we could have seen Blair go through pregnancy, her and Chuck finding out she was pregnant, Henry growing up. But still it’s so cute oh my goodness!!