diff --git a/package-lock.json b/package-lock.json
index 1017cfd7..562c8719 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -21,7 +21,7 @@
         "@next-auth/prisma-adapter": "^1.0.4",
         "@prisma/client": "^5.5.2",
         "@react-email/render": "^0.0.7",
-        "@sendgrid/mail": "^7.7.0",
+        "@sendgrid/mail": "^8.1.1",
         "classnames": "^2.3.2",
         "googleapis": "^117.0.0",
         "moment": "^2.30.1",
@@ -30,6 +30,7 @@
         "next": "^13.5.3",
         "next-auth": "^4.12.3",
         "react": "^18.2.0",
+        "react-datepicker": "^6.1.0",
         "react-dom": "^18.2.0",
         "react-hook-form": "^7.48.2",
         "uuidv4": "^6.2.13",
@@ -39,6 +40,7 @@
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         "@types/node": "18.0.0",
         "@types/react": "18.0.14",
+        "@types/react-datepicker": "^6.0.1",
         "@types/react-dom": "18.0.5",
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+      "resolved": "https://registry.npmjs.org/@esbuild/aix-ppc64/-/aix-ppc64-0.19.12.tgz",
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+      "dev": true,
+      "optional": true,
+      "os": [
+        "aix"
+      ],
+      "engines": {
+        "node": ">=12"
+      }
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-      "resolved": "https://registry.npmjs.org/@esbuild/android-arm/-/android-arm-0.18.20.tgz",
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+      "resolved": "https://registry.npmjs.org/@esbuild/android-arm/-/android-arm-0.19.12.tgz",
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@@ -118,9 +136,9 @@
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+      "resolved": "https://registry.npmjs.org/@esbuild/android-arm64/-/android-arm64-0.19.12.tgz",
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@@ -134,9 +152,9 @@
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+      "resolved": "https://registry.npmjs.org/@esbuild/android-x64/-/android-x64-0.19.12.tgz",
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@@ -150,9 +168,9 @@
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-      "resolved": "https://registry.npmjs.org/@esbuild/darwin-arm64/-/darwin-arm64-0.18.20.tgz",
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+      "resolved": "https://registry.npmjs.org/@esbuild/darwin-arm64/-/darwin-arm64-0.19.12.tgz",
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@@ -166,9 +184,9 @@
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+      "resolved": "https://registry.npmjs.org/@esbuild/darwin-x64/-/darwin-x64-0.19.12.tgz",
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@@ -182,9 +200,9 @@
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-      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-arm64/-/freebsd-arm64-0.18.20.tgz",
-      "integrity": "sha512-yqDQHy4QHevpMAaxhhIwYPMv1NECwOvIpGCZkECn8w2WFHXjEwrBn3CeNIYsibZ/iZEUemj++M26W3cNR5h+Tw==",
+      "version": "0.19.12",
+      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-arm64/-/freebsd-arm64-0.19.12.tgz",
+      "integrity": "sha512-4aRvFIXmwAcDBw9AueDQ2YnGmz5L6obe5kmPT8Vd+/+x/JMVKCgdcRwH6APrbpNXsPz+K653Qg8HB/oXvXVukA==",
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@@ -198,9 +216,9 @@
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-      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-x64/-/freebsd-x64-0.18.20.tgz",
-      "integrity": "sha512-tgWRPPuQsd3RmBZwarGVHZQvtzfEBOreNuxEMKFcd5DaDn2PbBxfwLcj4+aenoh7ctXcbXmOQIn8HI6mCSw5MQ==",
+      "version": "0.19.12",
+      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-x64/-/freebsd-x64-0.19.12.tgz",
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@@ -214,9 +232,9 @@
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-      "resolved": "https://registry.npmjs.org/@esbuild/linux-arm/-/linux-arm-0.18.20.tgz",
-      "integrity": "sha512-/5bHkMWnq1EgKr1V+Ybz3s1hWXok7mDFUMQ4cG10AfW3wL02PSZi5kFpYKrptDsgb2WAJIvRcDm+qIvXf/apvg==",
+      "version": "0.19.12",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-arm/-/linux-arm-0.19.12.tgz",
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@@ -230,9 +248,9 @@
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+      "resolved": "https://registry.npmjs.org/@esbuild/linux-arm64/-/linux-arm64-0.19.12.tgz",
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@@ -246,9 +264,9 @@
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-      "integrity": "sha512-P4etWwq6IsReT0E1KHU40bOnzMHoH73aXp96Fs8TIT6z9Hu8G6+0SHSw9i2isWrD2nbx2qo5yUqACgdfVGx7TA==",
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+      "resolved": "https://registry.npmjs.org/@esbuild/linux-ia32/-/linux-ia32-0.19.12.tgz",
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@@ -262,9 +280,9 @@
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-      "resolved": "https://registry.npmjs.org/@esbuild/linux-loong64/-/linux-loong64-0.18.20.tgz",
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+      "resolved": "https://registry.npmjs.org/@esbuild/linux-loong64/-/linux-loong64-0.19.12.tgz",
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@@ -278,9 +296,9 @@
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     "node_modules/@esbuild/linux-mips64el": {
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-      "resolved": "https://registry.npmjs.org/@esbuild/linux-mips64el/-/linux-mips64el-0.18.20.tgz",
-      "integrity": "sha512-d5NeaXZcHp8PzYy5VnXV3VSd2D328Zb+9dEq5HE6bw6+N86JVPExrA6O68OPwobntbNJ0pzCpUFZTo3w0GyetQ==",
+      "version": "0.19.12",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-mips64el/-/linux-mips64el-0.19.12.tgz",
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@@ -294,9 +312,9 @@
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-      "resolved": "https://registry.npmjs.org/@esbuild/linux-ppc64/-/linux-ppc64-0.18.20.tgz",
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@@ -310,9 +328,9 @@
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@@ -326,9 +344,9 @@
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+      "resolved": "https://registry.npmjs.org/@esbuild/linux-s390x/-/linux-s390x-0.19.12.tgz",
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@@ -342,9 +360,9 @@
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@@ -358,9 +376,9 @@
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@@ -374,9 +392,9 @@
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@@ -390,9 +408,9 @@
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@@ -509,14 +527,19 @@
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-        "@floating-ui/utils": "^0.1.3"
+        "@floating-ui/core": "^1.0.0",
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-        "@esbuild/win32-x64": "0.18.20"
+        "@esbuild/aix-ppc64": "0.19.12",
+        "@esbuild/android-arm": "0.19.12",
+        "@esbuild/android-arm64": "0.19.12",
+        "@esbuild/android-x64": "0.19.12",
+        "@esbuild/darwin-arm64": "0.19.12",
+        "@esbuild/darwin-x64": "0.19.12",
+        "@esbuild/freebsd-arm64": "0.19.12",
+        "@esbuild/freebsd-x64": "0.19.12",
+        "@esbuild/linux-arm": "0.19.12",
+        "@esbuild/linux-arm64": "0.19.12",
+        "@esbuild/linux-ia32": "0.19.12",
+        "@esbuild/linux-loong64": "0.19.12",
+        "@esbuild/linux-mips64el": "0.19.12",
+        "@esbuild/linux-ppc64": "0.19.12",
+        "@esbuild/linux-riscv64": "0.19.12",
+        "@esbuild/linux-s390x": "0.19.12",
+        "@esbuild/linux-x64": "0.19.12",
+        "@esbuild/netbsd-x64": "0.19.12",
+        "@esbuild/openbsd-x64": "0.19.12",
+        "@esbuild/sunos-x64": "0.19.12",
+        "@esbuild/win32-arm64": "0.19.12",
+        "@esbuild/win32-ia32": "0.19.12",
+        "@esbuild/win32-x64": "0.19.12"
       }
     },
     "node_modules/escalade": {
@@ -3384,6 +3663,19 @@
         "is-callable": "^1.1.3"
       }
     },
+    "node_modules/form-data": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/form-data/-/form-data-4.0.0.tgz",
+      "integrity": "sha512-ETEklSGi5t0QMZuiXoA/Q6vcnxcLQP5vdugSpuAyi6SVGi2clPPp+xgEhuMaHC+zGgn31Kd235W35f7Hykkaww==",
+      "dependencies": {
+        "asynckit": "^0.4.0",
+        "combined-stream": "^1.0.8",
+        "mime-types": "^2.1.12"
+      },
+      "engines": {
+        "node": ">= 6"
+      }
+    },
     "node_modules/fraction.js": {
       "version": "4.3.6",
       "resolved": "https://registry.npmjs.org/fraction.js/-/fraction.js-4.3.6.tgz",
@@ -4665,6 +4957,25 @@
         "node": ">=8.6"
       }
     },
+    "node_modules/mime-db": {
+      "version": "1.52.0",
+      "resolved": "https://registry.npmjs.org/mime-db/-/mime-db-1.52.0.tgz",
+      "integrity": "sha512-sPU4uV7dYlvtWJxwwxHD0PuihVNiE7TyAbQ5SWxDCB9mUYvOgroQOwYQQOKPJ8CIbE+1ETVlOoK1UC2nU3gYvg==",
+      "engines": {
+        "node": ">= 0.6"
+      }
+    },
+    "node_modules/mime-types": {
+      "version": "2.1.35",
+      "resolved": "https://registry.npmjs.org/mime-types/-/mime-types-2.1.35.tgz",
+      "integrity": "sha512-ZDY+bPm5zTTF+YpCrAU9nK0UgICYPT0QtT1NZWFv4s++TNkcgVaT0g6+4R2uI4MjQjzysHB1zxuWL50hzaeXiw==",
+      "dependencies": {
+        "mime-db": "1.52.0"
+      },
+      "engines": {
+        "node": ">= 0.6"
+      }
+    },
     "node_modules/minimatch": {
       "version": "3.1.2",
       "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-3.1.2.tgz",
@@ -4788,9 +5099,9 @@
       }
     },
     "node_modules/nanoid": {
-      "version": "3.3.6",
-      "resolved": "https://registry.npmjs.org/nanoid/-/nanoid-3.3.6.tgz",
-      "integrity": "sha512-BGcqMMJuToF7i1rt+2PWSNVnWIkGCU78jBG3RxO/bZlnZPK2Cmi2QaffxGO/2RvWi9sL+FAiRiXMgsyxQ1DIDA==",
+      "version": "3.3.7",
+      "resolved": "https://registry.npmjs.org/nanoid/-/nanoid-3.3.7.tgz",
+      "integrity": "sha512-eSRppjcPIatRIMC1U6UngP8XFcz8MQWGQdt1MTBQ7NaAmvXDfvNxbvWV3x2y6CdEUciCSsDHDQZbhYaB8QEo2g==",
       "funding": [
         {
           "type": "github",
@@ -4862,9 +5173,9 @@
       }
     },
     "node_modules/next-auth": {
-      "version": "4.23.1",
-      "resolved": "https://registry.npmjs.org/next-auth/-/next-auth-4.23.1.tgz",
-      "integrity": "sha512-mL083z8KgRtlrIV6CDca2H1kduWJuK/3pTS0Fe2og15KOm4v2kkLGdSDfc2g+019aEBrJUT0pPW2Xx42ImN1WA==",
+      "version": "4.24.6",
+      "resolved": "https://registry.npmjs.org/next-auth/-/next-auth-4.24.6.tgz",
+      "integrity": "sha512-djQt3ZEaWEIxcsuh3HTW2uuzLfXMRjHH+ugAsichlQSbH4iA5MRcgMA2HvTNvsDTDLh44tyU72+/gWsxgTbAKg==",
       "dependencies": {
         "@babel/runtime": "^7.20.13",
         "@panva/hkdf": "^1.0.2",
@@ -4877,7 +5188,7 @@
         "uuid": "^8.3.2"
       },
       "peerDependencies": {
-        "next": "^12.2.5 || ^13",
+        "next": "^12.2.5 || ^13 || ^14",
         "nodemailer": "^6.6.5",
         "react": "^17.0.2 || ^18",
         "react-dom": "^17.0.2 || ^18"
@@ -5538,6 +5849,11 @@
       "resolved": "https://registry.npmjs.org/proto-list/-/proto-list-1.2.4.tgz",
       "integrity": "sha512-vtK/94akxsTMhe0/cbfpR+syPuszcuwhqVjJq26CuNDgFGj682oRBXOP5MJpv2r7JtE8MsiepGIqvvOTBwn2vA=="
     },
+    "node_modules/proxy-from-env": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/proxy-from-env/-/proxy-from-env-1.1.0.tgz",
+      "integrity": "sha512-D+zkORCbA9f1tdWRK0RaCR3GPv50cMxcrz4X8k5LTSUD1Dkw47mKJEZQNunItRTkWwgtaUSo1RVFRIG9ZXiFYg=="
+    },
     "node_modules/punycode": {
       "version": "2.3.0",
       "resolved": "https://registry.npmjs.org/punycode/-/punycode-2.3.0.tgz",
@@ -5591,6 +5907,53 @@
         "node": ">=0.10.0"
       }
     },
+    "node_modules/react-datepicker": {
+      "version": "6.1.0",
+      "resolved": "https://registry.npmjs.org/react-datepicker/-/react-datepicker-6.1.0.tgz",
+      "integrity": "sha512-8uz+hAOpvHqZGvD4Ky1hJ0/tLI4S9B0Gu9LV7LtLxRKXODs/xrxEay0aMVp7AW9iizTeImZh/6aA00fFaRZpJw==",
+      "dependencies": {
+        "@floating-ui/react": "^0.26.2",
+        "classnames": "^2.2.6",
+        "date-fns": "^3.3.1",
+        "prop-types": "^15.7.2",
+        "react-onclickoutside": "^6.13.0"
+      },
+      "peerDependencies": {
+        "react": "^16.9.0 || ^17 || ^18",
+        "react-dom": "^16.9.0 || ^17 || ^18"
+      }
+    },
+    "node_modules/react-datepicker/node_modules/@floating-ui/react": {
+      "version": "0.26.9",
+      "resolved": "https://registry.npmjs.org/@floating-ui/react/-/react-0.26.9.tgz",
+      "integrity": "sha512-p86wynZJVEkEq2BBjY/8p2g3biQ6TlgT4o/3KgFKyTWoJLU1GZ8wpctwRqtkEl2tseYA+kw7dBAIDFcednfI5w==",
+      "dependencies": {
+        "@floating-ui/react-dom": "^2.0.8",
+        "@floating-ui/utils": "^0.2.1",
+        "tabbable": "^6.0.1"
+      },
+      "peerDependencies": {
+        "react": ">=16.8.0",
+        "react-dom": ">=16.8.0"
+      }
+    },
+    "node_modules/react-datepicker/node_modules/@floating-ui/react-dom": {
+      "version": "2.0.8",
+      "resolved": "https://registry.npmjs.org/@floating-ui/react-dom/-/react-dom-2.0.8.tgz",
+      "integrity": "sha512-HOdqOt3R3OGeTKidaLvJKcgg75S6tibQ3Tif4eyd91QnIJWr0NLvoXFpJA/j8HqkFSL68GDca9AuyWEHlhyClw==",
+      "dependencies": {
+        "@floating-ui/dom": "^1.6.1"
+      },
+      "peerDependencies": {
+        "react": ">=16.8.0",
+        "react-dom": ">=16.8.0"
+      }
+    },
+    "node_modules/react-datepicker/node_modules/@floating-ui/utils": {
+      "version": "0.2.1",
+      "resolved": "https://registry.npmjs.org/@floating-ui/utils/-/utils-0.2.1.tgz",
+      "integrity": "sha512-9TANp6GPoMtYzQdt54kfAyMmz1+osLlXdg2ENroU7zzrtflTLrrC/lgrIfaSe+Wu0b89GKccT7vxXA0MoAIO+Q=="
+    },
     "node_modules/react-dom": {
       "version": "18.2.0",
       "resolved": "https://registry.npmjs.org/react-dom/-/react-dom-18.2.0.tgz",
@@ -5623,6 +5986,19 @@
       "resolved": "https://registry.npmjs.org/react-is/-/react-is-16.13.1.tgz",
       "integrity": "sha512-24e6ynE2H+OKt4kqsOvNd8kBpV65zoxbA4BVsEOB3ARVWQki/DHzaUoC5KuON/BiccDaCCTZBuOcfZs70kR8bQ=="
     },
+    "node_modules/react-onclickoutside": {
+      "version": "6.13.0",
+      "resolved": "https://registry.npmjs.org/react-onclickoutside/-/react-onclickoutside-6.13.0.tgz",
+      "integrity": "sha512-ty8So6tcUpIb+ZE+1HAhbLROvAIJYyJe/1vRrrcmW+jLsaM+/powDRqxzo6hSh9CuRZGSL1Q8mvcF5WRD93a0A==",
+      "funding": {
+        "type": "individual",
+        "url": "https://github.com/Pomax/react-onclickoutside/blob/master/FUNDING.md"
+      },
+      "peerDependencies": {
+        "react": "^15.5.x || ^16.x || ^17.x || ^18.x",
+        "react-dom": "^15.5.x || ^16.x || ^17.x || ^18.x"
+      }
+    },
     "node_modules/read-cache": {
       "version": "1.0.0",
       "resolved": "https://registry.npmjs.org/read-cache/-/read-cache-1.0.0.tgz",
@@ -5759,18 +6135,34 @@
       }
     },
     "node_modules/rollup": {
-      "version": "3.29.4",
-      "resolved": "https://registry.npmjs.org/rollup/-/rollup-3.29.4.tgz",
-      "integrity": "sha512-oWzmBZwvYrU0iJHtDmhsm662rC15FRXmcjCk1xD771dFDx5jJ02ufAQQTn0etB2emNk4J9EZg/yWKpsn9BWGRw==",
+      "version": "4.12.0",
+      "resolved": "https://registry.npmjs.org/rollup/-/rollup-4.12.0.tgz",
+      "integrity": "sha512-wz66wn4t1OHIJw3+XU7mJJQV/2NAfw5OAk6G6Hoo3zcvz/XOfQ52Vgi+AN4Uxoxi0KBBwk2g8zPrTDA4btSB/Q==",
       "dev": true,
+      "dependencies": {
+        "@types/estree": "1.0.5"
+      },
       "bin": {
         "rollup": "dist/bin/rollup"
       },
       "engines": {
-        "node": ">=14.18.0",
+        "node": ">=18.0.0",
         "npm": ">=8.0.0"
       },
       "optionalDependencies": {
+        "@rollup/rollup-android-arm-eabi": "4.12.0",
+        "@rollup/rollup-android-arm64": "4.12.0",
+        "@rollup/rollup-darwin-arm64": "4.12.0",
+        "@rollup/rollup-darwin-x64": "4.12.0",
+        "@rollup/rollup-linux-arm-gnueabihf": "4.12.0",
+        "@rollup/rollup-linux-arm64-gnu": "4.12.0",
+        "@rollup/rollup-linux-arm64-musl": "4.12.0",
+        "@rollup/rollup-linux-riscv64-gnu": "4.12.0",
+        "@rollup/rollup-linux-x64-gnu": "4.12.0",
+        "@rollup/rollup-linux-x64-musl": "4.12.0",
+        "@rollup/rollup-win32-arm64-msvc": "4.12.0",
+        "@rollup/rollup-win32-ia32-msvc": "4.12.0",
+        "@rollup/rollup-win32-x64-msvc": "4.12.0",
         "fsevents": "~2.3.2"
       }
     },
@@ -6626,29 +7018,29 @@
       "dev": true
     },
     "node_modules/vite": {
-      "version": "4.4.11",
-      "resolved": "https://registry.npmjs.org/vite/-/vite-4.4.11.tgz",
-      "integrity": "sha512-ksNZJlkcU9b0lBwAGZGGaZHCMqHsc8OpgtoYhsQ4/I2v5cnpmmmqe5pM4nv/4Hn6G/2GhTdj0DhZh2e+Er1q5A==",
+      "version": "5.1.4",
+      "resolved": "https://registry.npmjs.org/vite/-/vite-5.1.4.tgz",
+      "integrity": "sha512-n+MPqzq+d9nMVTKyewqw6kSt+R3CkvF9QAKY8obiQn8g1fwTscKxyfaYnC632HtBXAQGc1Yjomphwn1dtwGAHg==",
       "dev": true,
       "dependencies": {
-        "esbuild": "^0.18.10",
-        "postcss": "^8.4.27",
-        "rollup": "^3.27.1"
+        "esbuild": "^0.19.3",
+        "postcss": "^8.4.35",
+        "rollup": "^4.2.0"
       },
       "bin": {
         "vite": "bin/vite.js"
       },
       "engines": {
-        "node": "^14.18.0 || >=16.0.0"
+        "node": "^18.0.0 || >=20.0.0"
       },
       "funding": {
         "url": "https://github.com/vitejs/vite?sponsor=1"
       },
       "optionalDependencies": {
-        "fsevents": "~2.3.2"
+        "fsevents": "~2.3.3"
       },
       "peerDependencies": {
-        "@types/node": ">= 14",
+        "@types/node": "^18.0.0 || >=20.0.0",
         "less": "*",
         "lightningcss": "^1.21.0",
         "sass": "*",
@@ -6703,6 +7095,34 @@
         "url": "https://opencollective.com/vitest"
       }
     },
+    "node_modules/vite/node_modules/postcss": {
+      "version": "8.4.35",
+      "resolved": "https://registry.npmjs.org/postcss/-/postcss-8.4.35.tgz",
+      "integrity": "sha512-u5U8qYpBCpN13BsiEB0CbR1Hhh4Gc0zLFuedrHJKMctHCHAGrMdG0PRM/KErzAL3CU6/eckEtmHNB3x6e3c0vA==",
+      "dev": true,
+      "funding": [
+        {
+          "type": "opencollective",
+          "url": "https://opencollective.com/postcss/"
+        },
+        {
+          "type": "tidelift",
+          "url": "https://tidelift.com/funding/github/npm/postcss"
+        },
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/ai"
+        }
+      ],
+      "dependencies": {
+        "nanoid": "^3.3.7",
+        "picocolors": "^1.0.0",
+        "source-map-js": "^1.0.2"
+      },
+      "engines": {
+        "node": "^10 || ^12 || >=14"
+      }
+    },
     "node_modules/vitest": {
       "version": "0.34.6",
       "resolved": "https://registry.npmjs.org/vitest/-/vitest-0.34.6.tgz",
diff --git a/package.json b/package.json
index 4fd77d6f..980612c2 100644
--- a/package.json
+++ b/package.json
@@ -23,7 +23,7 @@
     "@next-auth/prisma-adapter": "^1.0.4",
     "@prisma/client": "^5.5.2",
     "@react-email/render": "^0.0.7",
-    "@sendgrid/mail": "^7.7.0",
+    "@sendgrid/mail": "^8.1.1",
     "classnames": "^2.3.2",
     "googleapis": "^117.0.0",
     "moment": "^2.30.1",
@@ -32,6 +32,7 @@
     "next": "^13.5.3",
     "next-auth": "^4.12.3",
     "react": "^18.2.0",
+    "react-datepicker": "^6.1.0",
     "react-dom": "^18.2.0",
     "react-hook-form": "^7.48.2",
     "uuidv4": "^6.2.13",
@@ -41,6 +42,7 @@
   "devDependencies": {
     "@types/node": "18.0.0",
     "@types/react": "18.0.14",
+    "@types/react-datepicker": "^6.0.1",
     "@types/react-dom": "18.0.5",
     "@typescript-eslint/eslint-plugin": "^5.33.0",
     "@typescript-eslint/parser": "^5.33.0",
diff --git a/src/components/file/AddFile.tsx b/src/components/file/AddFile.tsx
index 4b3de615..34db93ff 100644
--- a/src/components/file/AddFile.tsx
+++ b/src/components/file/AddFile.tsx
@@ -1,19 +1,49 @@
 import FileTile from "@components/file/FileTile";
 import { faFileCirclePlus } from "@fortawesome/free-solid-svg-icons";
 import { FontAwesomeIcon } from "@fortawesome/react-fontawesome";
+import { useState } from "react";
+import AddFilePopup from "@components/user/AddFile";
+import { File as PrismaFile, Prisma } from "@prisma/client";
+
+const AddFile = ({
+  seniorId,
+  seniorFolder,
+  files,
+}: {
+  seniorId: string;
+  seniorFolder: string;
+  files: PrismaFile[];
+}) => {
+  const [showAddFilePopUp, setShowAddFilePopUp] = useState<boolean>(false);
+
+  const handlePopUp = () => {
+    setShowAddFilePopUp(!showAddFilePopUp);
+  };
 
-const AddFile = () => {
   return (
-    <FileTile className="border-2 border-dark-teal">
-      <div className="flex h-full w-full cursor-pointer flex-col items-center justify-center gap-y-2.5">
-        <FontAwesomeIcon
-          icon={faFileCirclePlus}
-          className="text-dark-teal"
-          size="xl"
+    <div>
+      {showAddFilePopUp ? (
+        <AddFilePopup
+          showAddFilePopUp={showAddFilePopUp}
+          setShowAddFilePopUp={setShowAddFilePopUp}
+          seniorId={seniorId}
+          files={files}
+          folder={seniorFolder}
         />
-        <h1 className="text-lg text-dark-teal">New File</h1>
-      </div>
-    </FileTile>
+      ) : null}
+      <button onClick={handlePopUp}>
+        <FileTile className="border-2 border-dark-teal">
+          <div className="flex h-full w-full cursor-pointer flex-col items-center justify-center gap-y-2.5">
+            <FontAwesomeIcon
+              icon={faFileCirclePlus}
+              className="text-dark-teal"
+              size="xl"
+            />
+            <h1 className="text-lg text-dark-teal">New File</h1>
+          </div>
+        </FileTile>
+      </button>
+    </div>
   );
 };
 
diff --git a/src/components/senior/DisplaySenior.tsx b/src/components/senior/DisplaySenior.tsx
index bbcd7c3f..b3674357 100644
--- a/src/components/senior/DisplaySenior.tsx
+++ b/src/components/senior/DisplaySenior.tsx
@@ -47,7 +47,6 @@ const FILES: PrismaFile[] = [
 const DisplaySenior = (props: DisplayProps) => {
   const { editable, canAddFile, senior } = props;
   const addFileId = uuid();
-
   return (
     <div className="flex flex-col gap-y-6">
       {/* @TODO - Firstname + lastname */}
@@ -56,9 +55,18 @@ const DisplaySenior = (props: DisplayProps) => {
       <Assignment editable={editable} senior={senior} />
       <SearchableContainer
         display={(file) => <File key={file.id} file={file} />}
-        elements={FILES} // TODO(nickbar01234) - Replace with real data
+        elements={FILES} // TODO(nickbar01234) - Replace with real data.
         search={(file, filter) => formatFileDate(file.date).includes(filter)}
-        addElementComponent={canAddFile && <AddFile key={addFileId} />}
+        addElementComponent={
+          canAddFile && (
+            <AddFile
+              seniorId={senior.id}
+              seniorFolder={senior.folder}
+              files={senior.Files}
+              key={addFileId}
+            />
+          )
+        }
         emptyNode={
           <p className="text-2xl font-light text-[#000022]">No files yet.</p>
         }
diff --git a/src/components/user/AddFile.tsx b/src/components/user/AddFile.tsx
new file mode 100644
index 00000000..74ba6215
--- /dev/null
+++ b/src/components/user/AddFile.tsx
@@ -0,0 +1,226 @@
+"use client";
+
+import React, { Dispatch, SetStateAction, useState } from "react";
+import FilterDropdown from "@components/FilterDropdown";
+import Tag, { TagProps, tagList } from "@components/Tag";
+import DatePicker from "react-datepicker";
+import "react-datepicker/dist/react-datepicker.css";
+import { createFile } from "@api/file/route.client";
+import { File as PrismaFile, Prisma } from "@prisma/client";
+import { Checkbox, button } from "@material-tailwind/react";
+import { setActive } from "@material-tailwind/react/components/Tabs/TabsContext";
+import { FontAwesomeIcon } from "@fortawesome/react-fontawesome";
+import { faCalendar } from "@fortawesome/free-solid-svg-icons";
+
+type AddFileProps = {
+  showAddFilePopUp: boolean;
+  setShowAddFilePopUp: Dispatch<SetStateAction<boolean>>;
+  seniorId: string;
+  files: PrismaFile[];
+  folder: string;
+};
+
+const TagOptions = ({
+  selectedTags,
+  setSelectedTags,
+}: {
+  selectedTags: TagProps[];
+  setSelectedTags: React.Dispatch<React.SetStateAction<TagProps[]>>;
+}) => {
+  return (
+    <div className="flex grid-flow-row flex-wrap">
+      {tagList.map((tag) => (
+        <div key={tag.name}>
+          <input
+            type="checkbox"
+            id={tag.name}
+            className="size-40 peer my-5 hidden"
+            onClick={() => {
+              if (!selectedTags.includes(tag) && selectedTags.length < 3) {
+                setSelectedTags([...selectedTags, tag]);
+              } else {
+                setSelectedTags(selectedTags.filter((i) => i != tag));
+              }
+            }}
+          />
+          {!selectedTags.includes(tag) && (
+            <label
+              htmlFor={tag.name}
+              className="m-2 ml-[-2px] inline-block rounded-full border-2 p-2 hover:bg-white hover:text-[#22555A]"
+            >
+              {" "}
+              {tag.name}
+            </label>
+          )}
+          {selectedTags.includes(tag) && (
+            <label
+              htmlFor={tag.name}
+              className="m-2 ml-[-2px] inline-block rounded-full border-2 bg-white p-2 text-[#22555A]"
+            >
+              {" "}
+              {tag.name}
+            </label>
+          )}
+        </div>
+      ))}
+    </div>
+  );
+};
+
+const TagSelector = ({
+  selectedTags,
+  setSelectedTags,
+}: {
+  selectedTags: TagProps[];
+  setSelectedTags: React.Dispatch<React.SetStateAction<TagProps[]>>;
+}) => {
+  return (
+    <div>
+      <div className="text-neutral-600 mb-1 h-[34px] w-full font-['merriweather'] text-2xl">
+        Tags
+      </div>
+      <div className="text-lg font-thin">
+        Select min of 1, max of 3 <span className="text-red-400">*</span>
+      </div>
+      <TagOptions
+        selectedTags={selectedTags}
+        setSelectedTags={setSelectedTags}
+      />
+    </div>
+  );
+};
+
+const AddFile = ({
+  showAddFilePopUp,
+  setShowAddFilePopUp,
+  seniorId,
+  files,
+  folder,
+}: AddFileProps) => {
+  const currFiles = Object.values(files);
+  const excludeDates = currFiles.map((fileObj) => fileObj.date);
+  const excludedDatesString = excludeDates.map((dateObj) =>
+    dateObj.toDateString()
+  );
+
+  const startDate_ = new Date();
+
+  while (excludedDatesString.includes(startDate_.toDateString())) {
+    startDate_.setDate(startDate_.getDate() + 1);
+  }
+
+  const [startDate, setStartDate] = useState(startDate_);
+
+  const [confirm, setConfirm] = useState<boolean>(false);
+  const [error, setError] = useState<boolean>(false);
+  const [selectedTags, setSelectedTags] = useState<TagProps[]>([]);
+  const [datePickerOpen, setDatePickerOpen] = useState(false);
+
+  const handleCancel = () => {
+    setShowAddFilePopUp(!showAddFilePopUp);
+  };
+
+  const callAddFile = async () => {
+    const response = await createFile({
+      body: {
+        date: startDate,
+        filetype: "Google Document",
+        url: "",
+        Tags: selectedTags.map((tagProp) => tagProp.name),
+        seniorId: seniorId,
+      },
+    });
+
+    if (response.code == "SUCCESS") {
+      setConfirm(true);
+    } else {
+      setError(true);
+    }
+  };
+
+  return (
+    <>
+      {showAddFilePopUp && (
+        <div className="absolute left-0 top-0 z-50 flex h-screen w-screen flex-row place-content-center items-start justify-center backdrop-blur-[2px] backdrop-brightness-75">
+          {!confirm && !error ? (
+            <div className="mt-20 flex h-2/3 w-2/5 flex-col justify-between rounded-[16px] bg-[#22555A] p-10 font-['merriweather'] text-white">
+              <div className="mb-5 mt-4 text-3xl font-bold">
+                {" "}
+                Create New File{" "}
+              </div>
+              <div className="text-neutral-600 mb-3 h-[34px] w-full text-2xl font-thin">
+                Select Date
+              </div>
+              <div className="inline-bl w-full">
+                <div className="text-2xl text-[#22555A]">
+                  <DatePicker
+                    showIcon
+                    wrapperClassName="w-full relative"
+                    calendarIconClassname="text-3xl text-blue-600 mt-[7px] absolute right-2"
+                    className="mb-4 h-16 w-full rounded-lg pl-[50px] font-['merriweather']"
+                    selected={startDate}
+                    onChange={(date) => date && setStartDate(date)}
+                    dateFormat="dd MMMM yyyy"
+                    excludeDates={excludeDates}
+                  />
+                </div>
+              </div>
+              <TagSelector
+                selectedTags={selectedTags}
+                setSelectedTags={setSelectedTags}
+              />
+              <div className="flex w-full flex-row justify-center">
+                <button
+                  className="mx-2 my-4 w-full max-w-[9rem] rounded-[16px] bg-white p-3 text-2xl font-medium text-[#22555A] drop-shadow-md hover:bg-offer-white"
+                  onClick={handleCancel}
+                >
+                  Cancel
+                </button>
+                <button
+                  className="mx-2 my-4 w-full max-w-[9rem] rounded-[16px] p-3 text-2xl font-medium text-[#22555A] drop-shadow-md hover:bg-offer-white enabled:bg-white disabled:bg-gray-500 disabled:text-gray-700"
+                  disabled={selectedTags.length == 0}
+                  onClick={callAddFile}
+                >
+                  Create
+                </button>
+              </div>
+            </div>
+          ) : (
+            <>
+              {confirm ? (
+                <div className="h-[250px] max-w-[35%] flex-row flex-col place-content-center gap-y-10 self-center rounded-lg bg-white p-10 text-center text-lg">
+                  <span>File added successfully!</span>
+                  <div className="flex w-full flex-row justify-center">
+                    <button
+                      className="bg-legacy-teal text-md mx-1 w-full max-w-[10rem] rounded p-3 font-serif font-normal text-white hover:bg-dark-teal"
+                      onClick={() => setShowAddFilePopUp(false)}
+                    >
+                      Confirm
+                    </button>
+                  </div>
+                </div>
+              ) : (
+                <div className="flex h-[250px] max-w-[35%] flex-col place-content-center gap-y-10 self-center rounded-lg bg-white p-10 text-center text-lg">
+                  <span>
+                    There was an error adding your file. Please reach out to
+                    your club administrator for assistance.
+                  </span>
+                  <div className="flex w-full flex-row justify-center">
+                    <button
+                      className="bg-legacy-teal text-md disabled: mx-1 w-full max-w-[10rem] rounded p-3 font-serif font-normal text-white hover:bg-dark-teal"
+                      onClick={() => setShowAddFilePopUp(false)}
+                    >
+                      Confirm
+                    </button>
+                  </div>
+                </div>
+              )}
+            </>
+          )}
+        </div>
+      )}
+    </>
+  );
+};
+
+export default AddFile;