Lua scripting solution

This is indeed possible using Lua scripting. You can use the script below (the number conversion is taken from rosettacode.org).

The script can do a boring option, which will translate 12:45 to "twelve forty-five", and an awesome option which will translate it to "a quarter to one". It also does a Uri Herrera option which does the hour bold ;)

Also it automatically refreshes, when the time changes.

words = {"one ", "two ", "three ", "four ", "five ", "six ", "seven ", "eight ", "nine "}

levels = {"thousand ", "million ", "billion ", "trillion ", "quadrillion ", "quintillion ", "sextillion ", "septillion ", "octillion ", [0] = ""}

iwords = {"ten ", "twenty ", "thirty ", "forty ", "fifty ", "sixty ", "seventy ", "eighty ", "ninety "}

twords = {"eleven ", "twelve ", "thirteen ", "fourteen ", "fifteen ", "sixteen ", "seventeen ", "eighteen ", "nineteen "}



function digits(n)

  local i, ret = -1

  return function()

    i, ret = i + 1, n % 10

    if n > 0 then

      n = math.floor(n / 10)

      return i, ret

    end

  end

end



level = false

function getname(pos, dig)

  level = level or pos % 3 == 0

  if(dig == 0) then return "" end

  local name = (pos % 3 == 1 and iwords[dig] or words[dig]) .. (pos % 3 == 2 and "hundred " or "")

  if(level) then name, level = name .. levels[math.floor(pos / 3)], false end

  return name

end



function numberToWord(number)

    if(number == 0) then return "zero" end

    vword = ""

    for i, v in digits(number) do

      vword = getname(i, v) .. vword

    end



    for i, v in ipairs(words) do

      vword = vword:gsub("ty " .. v, "ty-" .. v)

      vword = vword:gsub("ten " .. v, twords[i])

    end

    return vword

end



function conky_boringTime()

    hour = os.date("%H") + 0

    minute = os.date("%M") + 0

    return numberToWord(hour) .. numberToWord(minute)

end



function conky_awesomeTime()

    hour = os.date("%H") + 0

    minute = os.date("%M") + 0

    hour = hour % 12

    if(hour == 0) then 

        hour, nextHourWord = 12, "one " 

    else

        nextHourWord = numberToWord(hour+1)

    end

    hourWord = numberToWord(hour)

    if(minute == 0 ) then 

        return hourWord .. "o'clock"

    elseif(minute == 30) then

        return "half past " .. hourWord

    elseif(minute == 15) then

        return "a quarter past " .. hourWord 

    elseif(minute == 45) then

        return "a quarter to " .. nextHourWord 

    else

        if(minute < 30) then

            return numberToWord(minute) .. "past " .. hourWord

        else

            return numberToWord(60-minute) .. "to " .. nextHourWord

        end

    end

end



function conky_getHourWord()

    return numberToWord(os.date("%H") + 0)

end



function conky_getMinuteWord()

    return numberToWord(os.date("%M") + 0)

end

Now save it somewhere, for the purpose of this question assume we save it as ~/.config/conky/scripts/pretty_time.lua

Now edit your .conkyrc, before TEXT add a line

lua_load ~/.config/conky/scripts/pretty_time.lua

this loads the script so we can access the functions.

Then, at the appropriate place below TEXT, you can call the functions in the following way (conky automatically adds the conky_ prefix)

TEXT

...

${color grey}Boring time:$color ${lua boringTime}

${color grey}Awesome time:$color ${lua awesomeTime}

${color grey}Special Uri Herrera:$color ${font Aria:bold} ${lua getHourWord}$font ${lua getMinuteWord}

...

This will result in

If you want the seconds, this shouldn't be too hard to add yourself.