diff --git a/api/src/main/kotlin/com/gmtkgamejam/bot/BotMessageBuilder.kt b/api/src/main/kotlin/com/gmtkgamejam/bot/BotMessageBuilder.kt
new file mode 100644
index 00000000..540d5aa3
--- /dev/null
+++ b/api/src/main/kotlin/com/gmtkgamejam/bot/BotMessageBuilder.kt
@@ -0,0 +1,52 @@
+package com.gmtkgamejam.bot
+
+import com.gmtkgamejam.services.PostService
+import org.javacord.api.entity.message.embed.EmbedBuilder
+import org.javacord.api.entity.user.User
+
+class BotMessageBuilder {
+
+    private val postService = PostService()
+
+    fun canBuildEmbedFromUser(sender: User): Boolean = postService.getPostByAuthorId(sender.id.toString()) != null
+
+    fun embedMessage(recipient: User, sender: User): EmbedBuilder {
+        val post = postService.getPostByAuthorId(sender.id.toString())!!
+
+        val shortDescription = if (post.description.length > 240) post.description.take(237) + "..." else post.description
+
+        val embed = EmbedBuilder()
+            .setTitle("${sender.name} wants to get in contact!")
+            .setDescription("Hey there ${recipient.name}! ${sender.name} wants to get in touch - this is a summary of their current post on the Team Finder!")
+            .setAuthor("GMTK Team Finder", "https://findyourjam.team/", "https://findyourjam.team/logos/jam-logo-stacked.webp")
+            .addField("Description", shortDescription)
+
+        // Add optional fields - turns out this includes timezones
+        if (post.skillsSought?.isNotEmpty() == true) {
+            embed.addField("${sender.name} is looking for:", post.skillsSought.toString())
+        }
+        if (post.skillsPossessed?.isNotEmpty() == true) {
+            embed.addField("${sender.name} can bring:", post.skillsPossessed.toString())
+        }
+        if (post.preferredTools?.isNotEmpty() == true) {
+            embed.addField("Engine(s)", post.preferredTools.toString())
+        }
+        if (post.timezoneOffsets.isNotEmpty()) {
+            embed.addField("Timezone(s)", post.timezoneOffsets.map { if (it < 0) "UTC-$it" else "UTC+$it" }.toString())
+        }
+
+        embed
+            .addField("Like what you see?", "Check out their full post here to see more! https://findyourjam.team/gmtk/${post.id}/")
+            .setFooter("Feedback? DM @dotwo in the #developing-gtmk-team-finder-app channel")
+
+        return embed
+    }
+
+    // TODO: Add a variety of messages to mix things up a bit?
+    fun basicMessage(recipient: User, sender: User): String {
+        return """
+            Hey ${recipient.mentionTag}, ${sender.mentionTag} wants to get in contact about your Team Finder post!"
+            They don't have a post on the Team Finder yet, so why not drop them a message and find out more?
+        """.trimIndent()
+    }
+}
diff --git a/api/src/main/kotlin/com/gmtkgamejam/bot/DiscordBot.kt b/api/src/main/kotlin/com/gmtkgamejam/bot/DiscordBot.kt
index d0b357bf..682b0f64 100644
--- a/api/src/main/kotlin/com/gmtkgamejam/bot/DiscordBot.kt
+++ b/api/src/main/kotlin/com/gmtkgamejam/bot/DiscordBot.kt
@@ -1,7 +1,9 @@
 package com.gmtkgamejam.bot
 
 import com.gmtkgamejam.Config
+import kotlinx.coroutines.Dispatchers
 import kotlinx.coroutines.future.await
+import kotlinx.coroutines.withContext
 import org.javacord.api.DiscordApi
 import org.javacord.api.DiscordApiBuilder
 import org.javacord.api.entity.channel.ServerTextChannel
@@ -13,6 +15,7 @@ import org.javacord.api.exception.DiscordException
 import org.javacord.api.exception.MissingPermissionsException
 import org.slf4j.Logger
 import org.slf4j.LoggerFactory
+import kotlin.jvm.optionals.getOrElse
 
 class DiscordBot {
 
@@ -24,6 +27,8 @@ class DiscordBot {
 
     private lateinit var channel: ServerTextChannel
 
+    private val messageBuilder = BotMessageBuilder()
+
     private val approvedUsers: MutableList<String> = mutableListOf()
 
     init {
@@ -51,6 +56,26 @@ class DiscordBot {
         val recipient: User = api.getUserById(recipientUserId).await()
         val sender: User = api.getUserById(senderUserId).await()
 
+        val dmChannel = recipient.privateChannel.getOrElse { recipient.openPrivateChannel().get() }
+
+        val messageSendAttempt = if (messageBuilder.canBuildEmbedFromUser(sender)) {
+            dmChannel.sendMessage(messageBuilder.embedMessage(recipient, sender))
+        } else {
+            dmChannel.sendMessage(messageBuilder.basicMessage(recipient, sender))
+        }
+
+        try {
+            withContext(Dispatchers.IO) {
+                messageSendAttempt.get()
+            }
+        } catch (ex: InterruptedException) {
+            createFallbackChannelPingMessage(recipient, sender)
+        } catch (ex: java.util.concurrent.ExecutionException) {
+            createFallbackChannelPingMessage(recipient, sender)
+        }
+    }
+
+    private suspend fun createFallbackChannelPingMessage(recipient: User, sender: User) {
         val messageContents = "Hey ${recipient.mentionTag}, ${sender.mentionTag} wants to get in contact about your Team Finder post!"
         // TODO: Validate message actually sent, give error otherwise
         channel.sendMessage(messageContents).await()
diff --git a/api/src/main/kotlin/com/gmtkgamejam/models/posts/Skills.kt b/api/src/main/kotlin/com/gmtkgamejam/models/posts/Skills.kt
index 70111fb0..df82a772 100644
--- a/api/src/main/kotlin/com/gmtkgamejam/models/posts/Skills.kt
+++ b/api/src/main/kotlin/com/gmtkgamejam/models/posts/Skills.kt
@@ -1,13 +1,17 @@
 package com.gmtkgamejam.models.posts
 
-enum class Skills {
-    ART_2D,
-    ART_3D,
-    CODE,
-    DESIGN_PRODUCTION,
-    SFX,
-    MUSIC,
-    TESTING_SUPPORT,
-    TEAM_LEAD,
-    OTHER;
+enum class Skills(private var readableName: String) {
+    ART_2D("2D Art"),
+    ART_3D("3D Art"),
+    CODE("Code"),
+    DESIGN_PRODUCTION("Design/Production"),
+    SFX("SFX"),
+    MUSIC("Music"),
+    TESTING_SUPPORT("Testing/Support"),
+    TEAM_LEAD("Team lead"),
+    OTHER("Other");
+
+    override fun toString(): String {
+        return readableName;
+    }
 }
diff --git a/api/src/main/kotlin/com/gmtkgamejam/models/posts/Tools.kt b/api/src/main/kotlin/com/gmtkgamejam/models/posts/Tools.kt
index 1bbc8838..0fa81a27 100644
--- a/api/src/main/kotlin/com/gmtkgamejam/models/posts/Tools.kt
+++ b/api/src/main/kotlin/com/gmtkgamejam/models/posts/Tools.kt
@@ -1,15 +1,19 @@
 package com.gmtkgamejam.models.posts
 
 // For the time being, Tool == Engine
-enum class Tools {
-    UNITY,
-    CONSTRUCT,
-    GAME_MAKER_STUDIO,
-    GODOT,
-    TWINE,
-    BITSY,
-    UNREAL,
-    RPG_MAKER,
-    PICO_8,
-    OTHER,
+enum class Tools(private var readableName: String) {
+    UNITY("Unity"),
+    CONSTRUCT("Construct"),
+    GAME_MAKER_STUDIO("Game Maker Studio"),
+    GODOT("Godot"),
+    TWINE("Twine"),
+    BITSY("Bitsy"),
+    UNREAL("Unreal"),
+    RPG_MAKER("RPG Maker"),
+    PICO_8("PICO 8"),
+    OTHER("Other");
+
+    override fun toString(): String {
+        return readableName;
+    }
 }
\ No newline at end of file
diff --git a/ui/src/pages/post/Post.tsx b/ui/src/pages/post/Post.tsx
index 6d28ec88..509fe0dc 100644
--- a/ui/src/pages/post/Post.tsx
+++ b/ui/src/pages/post/Post.tsx
@@ -154,7 +154,7 @@ const MessageOnDiscordButton: React.FC<{
             {canPostAuthorBeDMd && <DiscordMessageButton authorId={authorId} author={author} isLoggedIn={isLoggedIn} />}
 
             {inDiscordServer
-                ? <DiscordPingButton authorId={authorId} createBotDmMutation={createBotDmMutation} message={fallbackPingMessage} />
+                ? <DiscordPingButton authorId={authorId} authorName={author} createBotDmMutation={createBotDmMutation} message={fallbackPingMessage} />
                 : <>
                     <p>Sorry, you can&apos;t contact this user right now.</p>
                     <p>
diff --git a/ui/src/pages/post/components/DiscordPingButton.tsx b/ui/src/pages/post/components/DiscordPingButton.tsx
index b11ae20d..bb7ebcd4 100644
--- a/ui/src/pages/post/components/DiscordPingButton.tsx
+++ b/ui/src/pages/post/components/DiscordPingButton.tsx
@@ -1,14 +1,29 @@
 import React from "react";
+import {toast} from "react-hot-toast";
 
 export const DiscordPingButton: React.FC<{
     authorId: string,
+    authorName: string,
     createBotDmMutation: any,
     message: string
 }> = ({
     authorId,
+    authorName,
     createBotDmMutation,
     message,
 }) => {
+
+    const onClick = () => {
+        createBotDmMutation.mutate({
+            recipientId: authorId,
+        }, {
+            onSuccess: () => {
+                toast(`${authorName} has just been notified that you want to get in touch!`);
+            },
+
+        });
+    };
+
     return (
         <>
             <p className="mb-2">{message}</p>
@@ -16,7 +31,7 @@ export const DiscordPingButton: React.FC<{
                 <a
                     target="_blank"
                     rel="noreferrer"
-                    onClick={() => createBotDmMutation.mutate({ recipientId: authorId })}
+                    onClick={onClick}
                     className="text-sm"
                 >
                     Ping them on Discord