diff --git a/database/entities/Relationship.ts b/database/entities/Relationship.ts
index 8deaa0e2..696a5b49 100644
--- a/database/entities/Relationship.ts
+++ b/database/entities/Relationship.ts
@@ -4,7 +4,9 @@ import { Relationships } from "~/drizzle/schema";
 import type { User } from "~/packages/database-interface/user";
 import type { Relationship as APIRelationship } from "~/types/mastodon/relationship";
 
-export type Relationship = InferSelectModel<typeof Relationships>;
+export type Relationship = InferSelectModel<typeof Relationships> & {
+    requestedBy: boolean;
+};
 
 /**
  * Creates a new relationship between two users.
@@ -16,29 +18,32 @@ export const createNewRelationship = async (
     owner: User,
     other: User,
 ): Promise<Relationship> => {
-    return (
-        await db
-            .insert(Relationships)
-            .values({
-                ownerId: owner.id,
-                subjectId: other.id,
-                languages: [],
-                following: false,
-                showingReblogs: false,
-                notifying: false,
-                followedBy: false,
-                blocking: false,
-                blockedBy: false,
-                muting: false,
-                mutingNotifications: false,
-                requested: false,
-                domainBlocking: false,
-                endorsed: false,
-                note: "",
-                updatedAt: new Date().toISOString(),
-            })
-            .returning()
-    )[0];
+    return {
+        ...(
+            await db
+                .insert(Relationships)
+                .values({
+                    ownerId: owner.id,
+                    subjectId: other.id,
+                    languages: [],
+                    following: false,
+                    showingReblogs: false,
+                    notifying: false,
+                    followedBy: false,
+                    blocking: false,
+                    blockedBy: false,
+                    muting: false,
+                    mutingNotifications: false,
+                    requested: false,
+                    domainBlocking: false,
+                    endorsed: false,
+                    note: "",
+                    updatedAt: new Date().toISOString(),
+                })
+                .returning()
+        )[0],
+        requestedBy: false,
+    };
 };
 
 export const checkForBidirectionalRelationships = async (
@@ -81,6 +86,7 @@ export const relationshipToAPI = (rel: Relationship): APIRelationship => {
         muting_notifications: rel.mutingNotifications,
         notifying: rel.notifying,
         requested: rel.requested,
+        requested_by: rel.requestedBy,
         showing_reblogs: rel.showingReblogs,
         note: rel.note,
     };
diff --git a/database/entities/User.ts b/database/entities/User.ts
index 852555be..b82df81f 100644
--- a/database/entities/User.ts
+++ b/database/entities/User.ts
@@ -17,7 +17,7 @@ import { LogLevel } from "~/packages/log-manager";
 import type { Application } from "./Application";
 import type { EmojiWithInstance } from "./Emoji";
 import { objectToInboxRequest } from "./Federation";
-import { createNewRelationship } from "./Relationship";
+import { type Relationship, createNewRelationship } from "./Relationship";
 import type { Token } from "./Token";
 
 export type UserType = InferSelectModel<typeof Users>;
@@ -121,22 +121,33 @@ export const followRequestUser = async (
     reblogs = false,
     notify = false,
     languages: string[] = [],
-): Promise<InferSelectModel<typeof Relationships>> => {
+): Promise<Relationship> => {
     const isRemote = followee.isRemote();
 
-    const updatedRelationship = (
-        await db
-            .update(Relationships)
-            .set({
-                following: isRemote ? false : !followee.getUser().isLocked,
-                requested: isRemote ? true : followee.getUser().isLocked,
-                showingReblogs: reblogs,
-                notifying: notify,
-                languages: languages,
-            })
-            .where(eq(Relationships.id, relationshipId))
-            .returning()
-    )[0];
+    await db
+        .update(Relationships)
+        .set({
+            following: isRemote ? false : !followee.getUser().isLocked,
+            requested: isRemote ? true : followee.getUser().isLocked,
+            showingReblogs: reblogs,
+            notifying: notify,
+            languages: languages,
+        })
+        .where(eq(Relationships.id, relationshipId));
+
+    const updatedRelationship = await db.query.Relationships.findFirst({
+        where: (rel, { eq }) => eq(rel.id, relationshipId),
+        extras: {
+            requestedBy:
+                sql<boolean>`(SELECT "requested" FROM "Relationships" WHERE "Relationships"."ownerId" = ${followee.id} AND "Relationships"."subjectId" = ${follower.id})`.as(
+                    "requested_by",
+                ),
+        },
+    });
+
+    if (!updatedRelationship) {
+        throw new Error("Failed to update relationship");
+    }
 
     if (isRemote) {
         // Federate
@@ -165,16 +176,29 @@ export const followRequestUser = async (
                 } to ${followee.getUri()}`,
             );
 
-            return (
-                await db
-                    .update(Relationships)
-                    .set({
-                        following: false,
-                        requested: false,
-                    })
-                    .where(eq(Relationships.id, relationshipId))
-                    .returning()
-            )[0];
+            await db
+                .update(Relationships)
+                .set({
+                    following: false,
+                    requested: false,
+                })
+                .where(eq(Relationships.id, relationshipId));
+
+            const result = await db.query.Relationships.findFirst({
+                where: (rel, { eq }) => eq(rel.id, relationshipId),
+                extras: {
+                    requestedBy:
+                        sql<boolean>`(SELECT "requested" FROM "Relationships" WHERE "Relationships"."ownerId" = ${followee.id} AND "Relationships"."subjectId" = ${follower.id})`.as(
+                            "requested_by",
+                        ),
+                },
+            });
+
+            if (!result) {
+                throw new Error("Failed to update relationship");
+            }
+
+            return result;
         }
     } else {
         await db.insert(Notifications).values({
@@ -458,13 +482,19 @@ export const retrieveToken = async (
 export const getRelationshipToOtherUser = async (
     user: User,
     other: User,
-): Promise<InferSelectModel<typeof Relationships>> => {
+): Promise<Relationship> => {
     const foundRelationship = await db.query.Relationships.findFirst({
         where: (relationship, { and, eq }) =>
             and(
                 eq(relationship.ownerId, user.id),
                 eq(relationship.subjectId, other.id),
             ),
+        extras: {
+            requestedBy:
+                sql<boolean>`(SELECT "requested" FROM "Relationships" WHERE "Relationships"."ownerId" = ${other.id} AND "Relationships"."subjectId" = ${user.id})`.as(
+                    "requested_by",
+                ),
+        },
     });
 
     if (!foundRelationship) {
diff --git a/server/api/api/v1/accounts/relationships/index.ts b/server/api/api/v1/accounts/relationships/index.ts
index 7ccf080a..cf310ba6 100644
--- a/server/api/api/v1/accounts/relationships/index.ts
+++ b/server/api/api/v1/accounts/relationships/index.ts
@@ -1,6 +1,7 @@
 import { applyConfig, auth, handleZodError, qsQuery } from "@/api";
 import { errorResponse, jsonResponse } from "@/response";
 import { zValidator } from "@hono/zod-validator";
+import { sql } from "drizzle-orm";
 import type { Hono } from "hono";
 import { z } from "zod";
 import {
@@ -8,7 +9,7 @@ import {
     relationshipToAPI,
 } from "~/database/entities/Relationship";
 import { db } from "~/drizzle/db";
-import { RolePermissions } from "~/drizzle/schema";
+import { Relationships, RolePermissions } from "~/drizzle/schema";
 import { User } from "~/packages/database-interface/user";
 
 export const meta = applyConfig({
@@ -54,6 +55,12 @@ export default (app: Hono) =>
                         inArray(relationship.subjectId, ids),
                         eq(relationship.ownerId, self.id),
                     ),
+                extras: {
+                    requestedBy:
+                        sql<boolean>`(SELECT "requested" FROM "Relationships" WHERE "Relationships"."ownerId" = ${Relationships.id} AND "Relationships"."subjectId" = ${self.id})`.as(
+                            "requested_by",
+                        ),
+                },
             });
 
             const missingIds = ids.filter(
diff --git a/types/mastodon/relationship.ts b/types/mastodon/relationship.ts
index 1d5540de..c2bb9c2a 100644
--- a/types/mastodon/relationship.ts
+++ b/types/mastodon/relationship.ts
@@ -7,6 +7,7 @@ export type Relationship = {
     muting: boolean;
     muting_notifications: boolean;
     requested: boolean;
+    requested_by: boolean;
     domain_blocking: boolean;
     showing_reblogs: boolean;
     endorsed: boolean;