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i-willstealyourtoes · 1 year

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Hey 👋. It's so nice to see a fellow sleeping dogs fan! I was wondering if you had any headcanons for Wei, Jackie, and Winston?

Hi!! I agree, I was worried to think I was the only simp fan here! I apologise in advance for how out-of-character some of this might be, especially with Winston 😭

Also I feel like this turned into first date headcanons???? Mb lol-

Wei, Jackie and Winston and their s/o

Wei

- Okay I know its confirmed that Wei is a player so

- I think in the very start of y'all being flirty and stuff, he'd definitely still be 'in the market' or whatever

- Although, when he met you he definitely did keep back a little bit

- Not to put you on a pedestal, but he was quite charmed from the very beginning

- Anyways, I think he was most enchanted by either your sense of humour, your down to earth vibe or that laugh of yours

- Maybe all 3? Yeah, probably all 3

- We know Wei is incredibly good at flirting so he'd definitely have no issue at all trying to get close with you (the og rizz master)

- Though he might have felt a little nervous the more he became attached to you

- I mean, with all the others he just kind of... liked them and then he moved on??

- You though??? He became rather attached to you :)

- I mean, you're different !! You're so... you?

- It's hard to describe okay, he just likes you alot

- So when he asks you out he does feel a little anxious

- 'Hey, so uh- You wanna go somewhere together? Like a date, I mean.'

- Like, what if you declined and you stopped being friends altogether??? 😭

- Ofc his fear melted when you agreed to date

- He wanted the first date to be something more... casual?

- But also pretty cool ofc bc you deserve something rlly nice

- He decided he was just going to take you to like... this really picturesque spot that had a view of the sea/the city

- Yes, he did indeed plan it correctly so you guys could watch the sunset <333

- 'See? Told you it'd be worth the trip. Best view in Hong Kong, right?'

- AAAAAA I LOVE THIS I LOVE MEN OML

- Y'all are sitting on a picnic blanket, just holding each other as the sun goes down

- You guys are so cute omg

- Anyway, you definitely stay and watch the starts too

- Y'all be stargazing, lying in each others arms

- Wei definitely felt something then

- Like... not the usual 'they're cool I think I want them'

- He felt like 'omg I love them I want to stay like this please'

- It's quite late when you leave bc ig you lost all sense of time???

- (Same tbh I do this even if I'm not in some muscular guys arms)

- 'Aw shit, I didn't realise it was that late already. Should we go?'

- That last phrase was a question bc honestly, he didn't want to leave

- Okay okay but before y'all parted ways (he'd walk you home or something btw dw) he'd definitely ask you for another date

- 'So, how about this time next week then? If you're free, that is.'

- Eeee y'all are so cute

- Anyways, eventually you guys become partners and everything is great bc yessss

- Whether this is when he's a a triad member/red pole or a policeman, he still gets quite protective of you bc ofc

- Like, when he's a triad member, people don't like him

- When he's a red pole, people REALLY don't like him

- And when he reveals himself as a cop? ALOTTA PEOPLE REALLY REALLY DON'T LIKE HIM-

- This means people might go for you bc they know he likes you

- But then again, do they really wanna go against The Wei Shen??? It's Wei Shen dude, do you really wanna mess with him???

- Still, he worries. He definitely tries to keep an eye on you, or make sure you text him immediately if anything happens

- 'Text me alright? If anything happens, just call me.'

- He's just a little guy

- Okay he's not little

- He's just a protective guy

- He love you ok leave him be

Jackie

- MY BLORBO OMG ILY

- (The 'ily' can be portrayed as platonic or romantic tbh I just love him)

- He's just a little guy ok

- Anyway, I think he'd start kind of flirting with you bc he does that with everyone he meets that he's mildly attracted to???

- But once you guys actually hang out, he realises he actually likes you alot tbh

- I think it's either how nice you are to him or your laugh/smile

- He gets butterflies thinking about you :)

- That's why he stops flirting with the others, bc he kind of just wants you?

- You always play his flirting as just part of his personality rather than him actually being interested in you

- Which makes it a bit more difficult for him bc now he doesn't really know how to show you he actually wants to date you

- He definitely asks Wei about it when they're just hanging out

- 'You know that good-looking (hair colour), (Y/n)? Uh yeah, that one. I uh... I kind of really like them, but I don't really know how to.... ask them out. They always play off my flirts as a joke or something! I don't know what to do man, I really like them!'

- Wei suggested he just straight up tell you his intentions rather than hint at it

- That did make him a little nervous bc while he doesn't usually beat around the bush, he doesn't want you to like... make fun of him or something

- But eventually Wei convinced him that even if you rejected him, you wouldn't bully him or something

- So one day you two are in the car with Wei (he's driving) and he just gives Jackie a look

- 'Oh! Right... hey, (Y/n)? So uh... do you wanna... go on a date sometime?'

- '....sure.'

- VSHSBJSJAN LET'S GOOOOOOO

- Wei and Jackie share a look like '>:]' bc ofc

- I think he would try do something really fancy??? But then panic bc he can't afford it

- Yes, he texted Wei about it

- Yes, Wei threatened the owners to let you two go in if they saw you

- (Thanks Wei, you a real one fr)

- Anyway, he got you a bouquet as well bc UGH HE'S JUST SO NICE

- It ends up the fancy stuff didn't really fill you up, nor was it that worth so

- (Luckily you guys ended up not paying as much as usual bc of Wei)

- He feels kinda bad bc it wasn't really that good

- But it ends up going pretty good bc you end up getting ice cream and just go on a walk under the stars :)

- You guys end up sitting on some stairs, holding ice cream and stuff

- HE EVEN GAINS THE COURAGE TO PUT HIS ARM AROUND YOU YAY

- OK ok anyway after you two become official, I think he gets much more comfortable around you bc he knows you like him back

- PDA bc yes

- And when the whole... buried alive stuff happens, he kind of... clings to you

- He's much more emotional around you and hugs you tight whenever, especially when you're both sleeping together (not in the sexual way)

- He has nightmares often, and feels really bad when you wake up/stay up with him

- 'Man... I- I'm sorry (Y/n)... I don't know... I don't know what to do.... I'm scared, (Y/n).'

- He does these nightly confessions often tbh... he feels so guilty in the morning though

- He's just... he's just a lovely guy please protect him

Winston

- I'm ngl I think Winston will not beat around the bush

- At least, not for long

- When he first meets you, he thinks your cool

- He eventually gravitates towards you bc of how nice you are to him

- Like, he literally kills people everyday and here you are just going ':) hi'

- Like okay why don't you just kiss me already (probably Winston's thoughts)

- In the week where he decides to try date you, the others kind of tease him lol

- More specifically behind his back (even more specifically Conroy, Wei and Jackie)

- If he finds out they're dead 💀

- Anyway, one day he just calls you and asks bc yes :)

- 'Hey, (Y/n)? I was wondering if you wanted to go out?'

- 'Sure, looking forward to it!'

- 'Yeah? Alright, good. I'll pick you up.'

- He's happy :) yay dating time

- I feel like maybe you'd just do something chill??

- Idk like if you guys are already good friends you'd probably just chill somewhere like a restaurant like the Golden Koi

- Winston doesn't want you to meet his mom straight away bc uhhhh

- 'Eat more lah, you get so skinny ah...' (Mrs. Chu with literally anyone even if you're healthy)

- If you guys didn't know each other that well, he'd probably take you to a different restaurant??? Maybe BamBam???? idk man

- Yes he might feel a little nervous bc uhhh idk he's just babygirl he gets like that sometimes with pretty people

- He'd probably have to leave early bc you know.... he's a red pole he kinda has work all the time

- 'Now?! I have to go now!? I'm busy with- But- You- Ugh... fine! Fine, I'm leaving now.... fuck.'

- He looks at you and feels rlly bad bc :'( we were on a date

- 'I... uh, sorry, (Y/n). Work.'

- 'Ah, it's okay, I had fun with you anyway :)'

- He had fun while he was with you though, but he might be mad at whoever called him though bc yes

- Okay after y'all became official, he probably just let's you meet the others too

- Most of the time you'll be chilling at Golden Koi (Mrs. Chu approves of your existence now congrats)

- He likes this bc when he's finished with work he can come back to have good food, see his mom and you!!

- Life is preeeetty good for him

- And yes, when he comes back he picks you up/hugs you :)

- Yay hugs with babygirl

- He may be really soft with you, but as soon as someone teases him he just gives a death glare to the person

- He also likes you staying at the Golden Koi alot cuz then he knows where you are = easier to protect you

- OH also unrelated but he gets kinda jealous quick so uh

- Just kith the man and tell him your his

- Okay that sounds a bit possessive of him damn

- Dw, if he goes too far just tell his mom she'll beat his goofy ahh (not actually.... okay maybe....)

- 'OW- Hey- Ma I- OW- Okay!! I'm sorry!' (live footage of Winston being beaten up by his mom with a spoon or something)

- He definitely does get possessive actually... he's working on it (not)

- Like not in a horrible way ig? But if ur not into that just tell him or something ok

- He won't be mad, he almost never gets mad at you (I know, shocking given his usual demeanour)

- I think he's quite soft with you bc... well he can't be mad all the time

- Overall, I think he's pretty nice to you :)

#sleepingdogsxreader #sleeping dogs #sleeping dogs game #weishen #jackie ma #Winston chu #x reader

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