AWK, 268 bytes

srand(){split("Yup0You doubt me?0Of course0... did I miss something?0plz send teh coffee0Watching this endless list of new questions never gets boring0Kinda sorta0You should totally drop that and use jQuery0¯\\_(ツ)_/¯0... good question",a,0)}$0=a[int(rand()*10+1)]

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Rust, 320 309 bytes

use rand::Rng;let f=||["Yup","You doubt me?","Of course","... did I miss something?","please send teh coffee","Watching this endless list of new questions never gets boring","Kinda sorta","You should totally drop that and use jQuery","¯\\_(ツ)_/¯","... good question"][rand::thread_rng().gen_range(0..10)];

Rust Playground

JavaScript, 297 287 285 277 265 bytes

-10 bytes by replacing Math.floor() with ~~()

-2 bytes by replacing ~~() with |0 thanks to Neil

-8 bytes by replacing array with string.split(',')

-12 bytes by placing options directly inside of alert() and replacing string.split(',') with string.split`,`

alert('Yup,You doubt me?,Of course,... did I miss something?,please send teh coffee,Watching this endless list of new questions never gets boring,Kinda sorta,You should totally drop that and use jQuery,¯\\_(ツ)_/¯,... good question'.split`,`[Math.random()*10|0])

Vyxal, 150 bytes

`Yup|λ⍎ řð me?|Of ⟑ₑ|... ¬⁌ I ɾ⟑ ⟇↜?|plz ¬Ĵ teh ʁƛ|←⍋ λ« ⊛⟑ λ′ of λÞ ∨Œ ∨ſ Ô₂ ℅⁑|ₑ¥ °⊛a|λ⍎ ƛð ∺⁂ ɽ∫ λ⟇ λ¬ λʗ jßø|\¯\\_(`12484C+`)_\\\¯|... ƛ∫ ⟇¹`+\|/℅

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I decided to use an alternate approach with the new built-ins

Retina, 232 228 bytes

Yup,You doubt me?,Of course,... did I miss something?,please send teh coffee,Watching this endless list of newqs never gets boring,Kinda sorta,You should totally drop that and use jQuery,¯\_(ツ)_/¯,... goodq
q
 question
?S`,

Try it online! Explanation: The first two stages replace the empty input with the given string, the second stage saving 4 bytes by deduplicating the substring question, while the last stage splits it on commas and outputs a random element. Note that the byte count has been adjusted for UTF-8 (Retina normally uses ISO-8859-1 if it can, which is why TIO only shows the character count rather than the byte count). Edit: I used @Leo's Retina Kolmogorov golfer to detect the duplication and save 4 bytes.

Pyth, 230 bytes

Oc"Yup	You doubt me?	Of course	... did I miss something?	plz send teh coffee	Watching this endless list of new questions never gets boring	Kinda sorta	You should totally drop that and use jQuery	¯\_(\u30C4)_/¯	... good question"\	

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Fun fact: If you used a "packed" string, the byte count would jump up to 388.

05AB1E, 123 bytes

Žmõ甡¸€îååªç€î”#`“Yup
ÿ¬³€á?
Of…£
...ƒ§ Iš§†á?
plzƒ¨ teh™²
ÿ€Œèႇ€‚€¢…醙–ÜÜÀ
ÿŠœa
ÿ‚©§À›Â€Š€ƒ€Å jÿ
¯\_(ÿ)_/¯
...‚¿†ä“¶¡Ω

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Note: Prints a random response with a trailing newline.

Golfed using @KevinCruijssen's well known golf tip.

Explanation

Žmõç                         # Push the katakana character 'ツ'
”¡¸€îååªç€î”#`               # Push some uncompressible words onto the stack
“...“                        # Then push a compressed string containing the following contents:
  Yup                        # "Yup"
  ÿ¬³ me?                    # "You doubt me?"
  Of…£                       # "Of course"
  ...ƒ§ Iš§†á?               # "... did I miss something?"
  plzƒ¨ teh™²                # "plz send teh coffee"
  ÿ€Œèႇ€‚…醙–ÜÜÀ          # "Watching this endless list of new questions never gets boring"
  ÿŠœa                       # "Kinda sorta"
  ÿ‚©§À›Â€Š€ƒ€Å jQuery       # "You should totally drop that and use jQuery"
  ¯\_(ÿ)_/¯                  # shruggy boy
  ...‚¿†ä                    # "... good question"

¶¡                           # Split the responses into a good ol' list
Ω                            # Randomly pick a response
                             # At the end, yell the response out to STDOUT implicitly

^{Random fact: I was in halfway in the making of this program when my laptop crashed. I had to start coding again. Oh well, at least my answer is winning at the time of writing this!}

Scala, 278 267 bytes

print("Yup#You doubt me?#Of course#... did I miss something?#plz send teh coffee#Watching this endless list of new questions never gets boring#Kinda sorta#You should totally drop that and use jQuery#¯\\_(ツ)_/¯#... good question".split("#")((math.random*10)toInt))

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• -21 Thanks to corvus-192!

Python 2, 240 bytes

Hexdump:

00000000: efbb bf65 7865 6322 2222 789c 3d4f 3b4e  ...exec"""x.=O;N
00000010: c430 10bd ca53 aa84 221c 8082 1a51 202a  .0...S.."....Q *
00000020: b4d2 4a6b 6f3c 498c 1c8f f18c 414b 0bf7  ..Jko<I.....AK..
00000030: d93b ec55 b808 0348 54a3 d1fb cf95 3754  .;.U...HT.....7T
00000040: 9f83 9db8 15ae 7a75 536a cc8a 69e5 3851  ......zuSj..i.8Q
00000050: dfed 5a71 f731 070f 31d4 bb1d 3704 6e47  ..Zq.1..1...7.nG
00000060: c546 b76e 1c47 8418 7087 2d8a 1865 235d  .F.n.G..p.-..e#]
00000070: 635e fe90 8539 e0a5 9168 e4ec 4a7a 8750  c^...9...h..Jz.P
00000080: 0e50 5a31 f13c 13b9 27af d30f 1fa6 1218  .PZ1.<..'.......
00000090: 98c8 6c52 1405 cfc8 f4f6 2f17 fb5e a962  ..lR....../..^.b
000000a0: 2115 1cd9 3a2e ee61 369f 5685 dce5 bc3f  !...:..a6.V....?
000000b0: f45f 1f9f c3e1 fa72 feed 282b b764 59ac  ._.....r..(+.dY.
000000c0: 3ea5 1342 e562 215e 6163 d184 f0fc d8a8  >..B.b!^ac......
000000d0: 9eba 514a 8ada 77ae 1b86 6f8b b863 c922  ..QJ..w...o..c."
000000e0: 2222 2e64 6563 6f64 6528 227a 6970 2229  "".decode("zip")

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PHP, 261 253 bytes

-8: Change <?php echo to <?= (@nthnchu)

<?=explode(",","Yup,You doubt me?,Of course,... did I miss something?,plz send teh coffee,Watching this endless list of new questions never gets boring,Kinda sorta,You should totally drop that and use jQuery,¯\_(ツ)_/¯,... good question")[rand(0,9)];

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Bash, 269 267 266 264 bytes

-2: @user42589

-1: @nthnchu

-2: @Nahuel Fouilleul

q=(Yup "You doubt me?" Of\ course "... did I miss something?" "plz send teh coffee" "Watching this endless list of new questions never gets boring" Kinda\ sorta "You should totally drop that and use jQuery" "¯\_(ツ)_/¯" "... good question");echo ${q[RANDOM%10]}

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Charcoal, 152 151 bytes

‽⊞Ｏ⪪”}∧Ｐπ↙!▶�▶τ×Ｂlal⁰FＷ⊕← ″»yε⦃σ$L}⊖0!…Ｒf»V?⌕ΦＹV'∕ⅉ)>ιη¤=▷∧p{<ψ;↶～⌊″≔↔≡m≦ζＸ"´j\`⁹WＳ⌕Ｖ›w}ＬV>ＤＴY(Y⪪h‽ＢＲＶ⌕↥↘⮌\L∨⁰ＭPφFY5^ＩG↑~c‖"⌕ν﹪ηVＥ\`êＶω”A¦¯\_(ツ)_/¯

Try it online! Link is to verbose version of code. Edit: Saved 1 byte by using A as a separator. Note: The deverbosifier claims 148 147 bytes, but I believe ¯ (like ツ) needs to be encoded using 3 bytes in Charcoal. Explanation: Charcoal can only compress strings of printable ASCII, so the shrug is appended separately.

    ”...”               Compressed string
   ⪪     ¶              Split on newlines
 ⊞Ｏ        ¯\_(ツ)_/¯    Push literal string
‽                       Random element
                        Implicitly print

K (oK), 237 bytes

`0:*1?";"\"Yup;You doubt me?;Of course;... did I miss something?;plz send teh coffee;Watching this endless list of new questions never gets boring;Kinda sorta;You should totally drop that and use jQuery;¯\\_(ツ)_/¯;... good question";

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If returning a string is acceptable, the leading `0: and trailing ; can be elided to save 4 bytes.

Python 3, 283 274 bytes

-9 bytes thanks to ovs

from random import*
print(choice('Yup,You doubt me?,Of course,... did I miss something?,please send teh coffee,Watching this endless list of new questions never gets boring,Kinda sorta,You should totally drop that and use jQuery,¯\_(ツ)_/¯,... good question'.split(',')))

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C (gcc), ^{294 290} 289 bytes

Saved 4 bytes thanks to ErikF!!!
Saved a byte thanks to ceilingcat!!!

*s[]={"Yup","You doubt me?","Of course","... did I miss something?","please send teh coffee","Watching this endless list of new questions never gets boring","Kinda sorta","You should totally drop that and use jQuery","¯\\_(ツ)_/¯","... good question"};f(){puts(s[rand(srand(time(0)))%10]);}

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Straightforward rand() selection from an array of strings.

R, 265 bytes

cat(sample(c('Yup','You doubt me?','Of course','... did I miss something?','please send teh coffee','Watching this endless list of new questions never gets boring','Kinda sorta','You should totally drop that and use jQuery','¯\\_(ツ)_/¯','... good question'),1))

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Jelly, 145 bytes

“þkċṁṚFọẏ_ỌƤ:ZfCðƓ$6ṛtẓ2JƇMɼ¤ẆƥyɼȧẒ¡ƇƘ9Ɲŀẏ®ỊH\.ƒgFĊ#Ọṁv;`Ä?ḄƒXƲeȥẹ$Ḟ-Ṿṙ"zḄfWẊkEƓẇẇṢ¶ż²ṘzḄ¢ɼQ2³{Ėṃ"B¡f÷ṅƇ0@bSḟ⁶E⁶ėẇefðRẹȤ»O_33o142+33+197¦12309ỌỴX

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Encodes the whole string but replacing the shrug with !\_(!)_/! (since ! doesn't show up in the string and only printable ASCII / newlines are allowed), and then replaces ! with the upper bar symbol, and then just sets the Japanese character at that index manually.

Then, split by newlines and select a random one.