diff --git a/changelog.txt b/changelog.txt
index 38f2477022..a760edab2c 100644
--- a/changelog.txt
+++ b/changelog.txt
@@ -44,6 +44,7 @@ Template for new versions:
 - `gui/notify`: new notification type: injured citizens; click to zoom to injured units; also displays a warning if your hospital is not functional (or if you have no hospital)
 - `prioritize`: new info panel on under-construction buildings showing if the construction job has been taken and by whom. click to zoom to builder; toggle high priority status for job if it's not yet taken and you need it to be built ASAP
 - `gui/pathable`: new "Depot" mode that shows whether wagons can path to your trade depot
+- `advtools`: automatically add a conversation option to "ask whereabouts of" for all your relationships (before, you could only ask whereabouts of people involved in rumors)
 - `gui/design`: all-new visually-driven UI for much improved usability
 
 ## Fixes
diff --git a/docs/advtools.rst b/docs/advtools.rst
index 6c904f36c4..3be128d4de 100644
--- a/docs/advtools.rst
+++ b/docs/advtools.rst
@@ -35,4 +35,7 @@ framework. They can be repositioned via `gui/overlay` or toggled via
 
 When enabled, this overlay will automatically add additional searchable
 keywords to conversation topics. In particular, topics that relate to slain
-enemies will gain the ``slay`` and ``kill`` keywords.
+enemies will gain the ``slay`` and ``kill`` keywords. It will also add additional
+conversation options for asking whereabouts of your relationships - in vanilla,
+you can only ask whereabouts of historical figures involved in rumors you personally
+witnessed or heard about.
diff --git a/internal/advtools/convo.lua b/internal/advtools/convo.lua
index cf2fc1a9bc..210d94854b 100644
--- a/internal/advtools/convo.lua
+++ b/internal/advtools/convo.lua
@@ -13,7 +13,7 @@ local adventure = df.global.game.main_interface.adventure
 -- Gets the keywords already present on the dialog choice
 local function getKeywords(choice)
     local keywords = {}
-    for _, keyword in ipairs(choice.key_word) do
+    for _, keyword in ipairs(choice.keywords) do
         table.insert(keywords, keyword.value:lower())
     end
     return keywords
@@ -22,8 +22,8 @@ end
 -- Adds a keyword to the dialog choice
 local function addKeyword(choice, keyword)
     local keyword_ptr = df.new('string')
-    keyword_ptr.value = keyword
-    choice.key_word:insert('#', keyword_ptr)
+    keyword_ptr.value = dfhack.toSearchNormalized(keyword)
+    choice.keywords:insert('#', keyword_ptr)
 end
 
 -- Adds multiple keywords to the dialog choice
@@ -45,7 +45,7 @@ local function generateKeywordsForChoice(choice)
     end
 
     -- generate keywords from useful words in the text
-    for _, data in ipairs(choice.print_string.text) do
+    for _, data in ipairs(choice.title.text) do
         for word in dfhack.toSearchNormalized(data.value):gmatch('%w+') do
             -- collect additional keywords based on the special words
             if word == 'slew' or word == 'slain' then
@@ -61,8 +61,95 @@ local function generateKeywordsForChoice(choice)
     addKeywords(choice, new_keywords)
 end
 
+-- Helper function to create new dialog choices, returns the created choice
+local function new_choice(choice_type, title, keywords)
+    local choice = df.adventure_conversation_choice_infost:new()
+    choice.cc = df.talk_choice:new()
+    choice.cc.type = choice_type
+    local text = df.new("string")
+    text.value = title
+    choice.title.text:insert("#", text)
+
+    if keywords ~= nil then
+        addKeywords(choice, keywords)
+    end
+    return choice
+end
+
+local function addWhereaboutsChoice(race, name, target_id, heard_of)
+    local title = "Ask for the whereabouts of the " .. race .. " " .. dfhack.TranslateName(name, true)
+    if heard_of then
+        title = title .. " (Heard of)"
+    end
+    local choice = new_choice(df.talk_choice_type.AskWhereabouts, title, dfhack.TranslateName(name):split())
+    -- insert before the last choice, which is usually "back"
+    adventure.conversation.conv_choice_info:insert(#adventure.conversation.conv_choice_info-1, choice)
+    choice.cc.invocation_target_hfid = target_id
+end
+
+local function addHistFigWhereaboutsChoice(profile)
+    local histfig = df.historical_figure.find(profile.histfig_id)
+    local race = ""
+    local creature = df.creature_raw.find(histfig.race)
+    if creature then
+        local caste = creature.caste[histfig.caste]
+        race = caste.caste_name[0]
+    end
+
+    addWhereaboutsChoice(race, histfig.name, histfig.id, profile._type == df.relationship_profile_hf_historicalst)
+end
+
+local function addIdentityWhereaboutsChoice(identity)
+    local identity_name = identity.name
+    local race = ""
+    local creature = df.creature_raw.find(identity.race)
+    if creature then
+        local caste = creature.caste[identity.caste]
+        race = caste.caste_name[0]
+    else
+        -- no race given for the identity, assume it's the histfig
+        local histfig = df.historical_figure.find(identity.histfig_id)
+        creature = df.creature_raw.find(histfig.race)
+        if creature then
+            local caste = creature.caste[histfig.caste]
+            race = caste.caste_name[0]
+        end
+    end
+    addWhereaboutsChoice(race, identity_name, identity.impersonated_hf)
+end
+
 -- Condense the rumor system choices
 local function rumorUpdate()
+    local conversation_state = adventure.conversation.conv_act.events[0].menu
+    -- add new conversation options depending on state
+
+    -- If we're asking about directions, add ability to ask about all our relationships - visual, historical and identities.
+    -- In vanilla, we're only allowed to ask for directions to people we learned in anything that's added to df.global.adventure.rumor
+    if conversation_state == df.conversation_state_type.AskDirections then
+        local adventurer_figure = df.historical_figure.find(dfhack.world.getAdventurer().hist_figure_id)
+        local relationships = adventurer_figure.info.relationships
+
+        local visual = relationships.hf_visual
+        local historical = relationships.hf_historical
+        local identity = relationships.hf_identity
+
+        for _, profile in ipairs(visual) do
+            addHistFigWhereaboutsChoice(profile)
+        end
+
+        -- This option will likely always fail unless the false identity is impersonating someone
+        -- but giving away the false identity's true historical figure feels cheap.
+        for _, profile in ipairs(identity) do
+            addIdentityWhereaboutsChoice(df.identity.find(profile.identity_id))
+        end
+
+        -- Historical entities go last so as to not give away fake identities
+        for _, profile in ipairs(historical) do
+            addHistFigWhereaboutsChoice(profile)
+        end
+    end
+
+    -- generate extra keywords for all options
     for i, choice in ipairs(adventure.conversation.conv_choice_info) do
         generateKeywordsForChoice(choice)
     end
@@ -78,6 +165,11 @@ AdvRumorsOverlay.ATTRS{
     frame={w=0, h=0},
 }
 
+local last_first_entry = nil
 function AdvRumorsOverlay:render()
+    -- Only update if the first entry pointer changed, this reliably indicates the list changed
+    if #adventure.conversation.conv_choice_info <= 0 or last_first_entry == adventure.conversation.conv_choice_info[0] then return end
+    -- Remember the last first entry. This entry changes even if we quit out and return on the same menu!
+    last_first_entry = adventure.conversation.conv_choice_info[0]
     rumorUpdate()
 end