TNG. Jean-Luc Picard Flirting With You Would Include...

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Him being really awkward when flirting; stumbling over his words and stuttering every few sentences

Him getting really frustrated because he's so confident on the bridge but when he's around you his knees turn to jelly and his tongue gets tied

You always having to stifle your giggles when he stutters because you find it so damn cute

You blushing when he compliments you – even though it took him a few tries to get the compliment right

Him always being cautious when flirting since he's the captain and he doesn't want to seem unprofessional.

Only flirting on off hours and when there's not many people around

Him being super sweet and kind to you, and always trying to make you smile

Because he's always too focused on the crew to worry about himself you always make sure to ask him how he's doing

Him being very humbled when you ask about him, then he gets all flustered because he doesn't usually talk about himself so he doesn't quite know what to say

You talking to your friends on the ship about it, though not revealing that it's the Captain in respect for his privacy

Riker would start catching on after seeing Jean-Luc stumbling over his words around you, always praising your work, and requesting for your help on assignments and away missions. Riker wouldn't say anything to Jean-Luc around others, but he might bring it up when the two of them are alone, and he would definitely talk to you about it, wanting all of the juicy details

When Jean-Luc tries to ask you on a date he'd be pretty awkward and shy because he'd be worried of you turning him down

"Y/N, if you're um, not busy—or if you're not on duty later—maybe you and I could uh..."

"Yes?" "We could eat...together..."

"Alone?"

"If you want to. If you don't we could go to Ten Forward. Or, I could ask Commander Riker what holodeck programs he's played recently... if you like the holodeck..."

"I'd love to go to the holodeck with you, Captain. What time?"

"Oh, um, twenty-one hundred hours? If that works for you. And please, call me Jean-Luc."

"That'd be perfect, Jean-Luc."

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