diff --git a/app/config.py.example b/app/config.py.example
index 57cfa211..2fc21168 100644
--- a/app/config.py.example
+++ b/app/config.py.example
@@ -33,3 +33,6 @@ email_conf = ConnectionConfig(
     MAIL_SSL=False,
     USE_CREDENTIALS=True,
 )
+
+# PATHS
+STATIC_ABS_PATH = os.path.abspath("static")
diff --git a/app/routers/__init__.py b/app/routers/__init__.py
index e69de29b..7170f990 100644
--- a/app/routers/__init__.py
+++ b/app/routers/__init__.py
@@ -0,0 +1,4 @@
+import nltk
+
+
+nltk.download('punkt')
diff --git a/app/routers/event_images.py b/app/routers/event_images.py
new file mode 100644
index 00000000..a04536a4
--- /dev/null
+++ b/app/routers/event_images.py
@@ -0,0 +1,217 @@
+from app import config
+from functools import lru_cache
+from nltk.tokenize import word_tokenize
+from typing import Optional
+from word_forms.lemmatizer import lemmatize
+
+import re
+
+
+FLAIRS_EXTENSION = '.jpg'
+FLAIRS_REL_PATH = f'{config.STATIC_ABS_PATH}\\event_flairs'
+IMAGES_RELATED_WORDS_MAP = {
+    'birthday': 'birthday',
+    'coffee': 'coffee',
+    'coffees': 'coffee',
+    'concert': 'concert',
+    'gig': 'concert',
+    'concerts': 'concert',
+    'gigs': 'concert',
+    'bicycle': 'cycle',
+    'cycling': 'cycle',
+    'bike': 'cycle',
+    'bicycles': 'cycle',
+    'bikes': 'cycle',
+    'biking': 'cycle',
+    'dentist': 'dentist',
+    'dentistry': 'dentist',
+    'dental': 'dentist',
+    'dinner': 'food',
+    'dinners': 'food',
+    'restaurant': 'food',
+    'restaurants': 'food',
+    'family meal': 'food',
+    'lunch': 'food',
+    'lunches': 'food',
+    'luncheon': 'food',
+    'cocktail': 'drank',
+    'drinks': 'drank',
+    'cocktails': 'drank',
+    'golf': 'golf',
+    'graduation': 'graduate',
+    'gym': 'gym',
+    'workout': 'gym',
+    'workouts': 'gym',
+    'haircut': 'haircut',
+    'hair': 'haircut',
+    'halloween': 'halloween',
+    'helloween': 'halloween',
+    "hallowe'en": 'halloween',
+    'allhalloween': 'halloween',
+    "all hallows' eve": 'halloween',
+    "all saints' Eve": 'halloween',
+    'hiking': 'hike',
+    'hike': 'hike',
+    'hikes': 'hike',
+    'kayaking': 'kayak',
+    'piano': 'music',
+    'singing': 'music',
+    'music class': 'music',
+    'choir practice': 'music',
+    'flute': 'music',
+    'orchestra': 'music',
+    'oboe': 'music',
+    'clarinet': 'music',
+    'saxophone': 'music',
+    'cornett': 'music',
+    'trumpet': 'music',
+    'contrabass': 'music',
+    'cello': 'music',
+    'trombone': 'music',
+    'tuba': 'music',
+    'music ensemble': 'music',
+    'string quartett': 'music',
+    'guitar lesson': 'music',
+    'classical music': 'music',
+    'choir': 'music',
+    'manicure': 'manicure',
+    'pedicure': 'manicure',
+    'manicures': 'manicure',
+    'pedicures': 'manicure',
+    'massage': 'massage',
+    'back rub': 'massage',
+    'backrub': 'massage',
+    'massages': 'massage',
+    'pills': 'pill',
+    'medicines': 'pill',
+    'medicine': 'pill',
+    'drug': 'pill',
+    'drugs': 'pill',
+    'ping pong': 'pingpong',
+    'table tennis': 'pingpong',
+    'ping-pong': 'pingpong',
+    'pingpong': 'pingpong',
+    'plan week': 'plan',
+    'plan quarter': 'plan',
+    'plan day': 'plan',
+    'plan vacation': 'plan',
+    'week planning': 'plan',
+    'vacation planning': 'plan',
+    'pokemon': 'pokemon',
+    'reading': 'read',
+    'newspaper': 'read',
+    'fridge repair': 'repair',
+    'handyman': 'repair',
+    'electrician': 'repair',
+    'diy': 'repair',
+    'jog': 'ran',
+    'jogging': 'ran',
+    'running': 'ran',
+    'jogs': 'ran',
+    'runs': 'ran',
+    'sail': 'sail',
+    'sailing': 'sail',
+    'boat cruise': 'sail',
+    'sailboat': 'sail',
+    'santa claus': 'santa',
+    'father christmas': 'santa',
+    'skiing': 'ski',
+    'ski': 'ski',
+    'skis': 'ski',
+    'snowboarding': 'ski',
+    'snowshoeing': 'ski',
+    'snow shoe': 'ski',
+    'snow boarding': 'ski',
+    'soccer': 'soccer',
+    'swim': 'swam',
+    'swimming': 'swam',
+    'swims': 'swam',
+    'tennis': 'tennis',
+    'thanksgiving': 'thanksgiving',
+    'wedding': 'wed',
+    'wedding eve': 'wed',
+    'wedding-eve party': 'wed',
+    'weddings': 'wed',
+    'christmas': 'christmas',
+    'xmas': 'christmas',
+    'x-mas': 'christmas',
+    'yoga': 'yoga',
+}
+
+
+def generate_flare_link_from_lemmatized_word(lemmatized_word: str) -> str:
+    """Generate a link to a flair by a given lemmatized word.
+
+    Args:
+        lemmatized_word (str): The lemmatized word.
+
+    Returns:
+        str: The suitable link.
+    """
+    return f'{FLAIRS_REL_PATH}\\{lemmatized_word}{FLAIRS_EXTENSION}'
+
+
+def remove_non_alphabet_chars(text: str) -> str:
+    """Remove non-alphabet chars from a given string
+
+    Args:
+        text (str): The string to remove the non-alphabet chars from.
+
+    Returns:
+        str: The string after the removal.
+    """
+    regex = re.compile('[^a-zA-Z]')
+    return regex.sub('', text)
+
+
+def get_image_name(related_word: str) -> Optional[str]:
+    """Search the key of a given value in IMAGES_RELATED_WORDS_MAP dictionary.
+
+    Args:
+        related_word (str): The value to search its key.
+
+    Returns:
+        str: The value's key in IMAGES_RELATED_WORDS_MAP dictionary.
+    """
+    shrunken = remove_non_alphabet_chars(related_word).lower()
+    return IMAGES_RELATED_WORDS_MAP.get(shrunken)
+
+
+@lru_cache(maxsize=32)
+def search_token_in_related_words(token: str) -> Optional[str]:
+    """Search a token in IMAGES_RELATED_WORDS_MAP dictionary.
+
+    Args:
+        token (str): The token to search.
+
+    Returns:
+        str: The link to the suitable image of the given token.
+    """
+    key = get_image_name(token)
+    if key:
+        return generate_flare_link_from_lemmatized_word(key)
+
+
+def attach_image_to_event(event_content: str) -> str:
+    """Get a link to the suitable image of a given token content.
+
+    Args:
+        event_content (str): The event content.
+
+    Returns:
+        str: The link to the suitable image of a given token content.
+    """
+    event_tokens = word_tokenize(event_content)
+    for token in event_tokens:
+        if token.isalnum():
+            try:
+                base_word = lemmatize(remove_non_alphabet_chars(token).lower())
+            except ValueError:
+                base_word = token
+            if base_word in IMAGES_RELATED_WORDS_MAP.values():
+                return generate_flare_link_from_lemmatized_word(base_word)
+            link = search_token_in_related_words(token)
+            if link:
+                return link
+            link = '#'
+    return link
diff --git a/app/static/event_flairs/birthday.jpg b/app/static/event_flairs/birthday.jpg
new file mode 100644
index 00000000..da5da73f
Binary files /dev/null and b/app/static/event_flairs/birthday.jpg differ
diff --git a/app/static/event_flairs/christmas.jpg b/app/static/event_flairs/christmas.jpg
new file mode 100644
index 00000000..5aa06898
Binary files /dev/null and b/app/static/event_flairs/christmas.jpg differ
diff --git a/app/static/event_flairs/coffee.jpg b/app/static/event_flairs/coffee.jpg
new file mode 100644
index 00000000..aec0c0e8
Binary files /dev/null and b/app/static/event_flairs/coffee.jpg differ
diff --git a/app/static/event_flairs/concert.jpg b/app/static/event_flairs/concert.jpg
new file mode 100644
index 00000000..5d383cbf
Binary files /dev/null and b/app/static/event_flairs/concert.jpg differ
diff --git a/app/static/event_flairs/cycle.jpg b/app/static/event_flairs/cycle.jpg
new file mode 100644
index 00000000..62a3509a
Binary files /dev/null and b/app/static/event_flairs/cycle.jpg differ
diff --git a/app/static/event_flairs/dentist.jpg b/app/static/event_flairs/dentist.jpg
new file mode 100644
index 00000000..e4075202
Binary files /dev/null and b/app/static/event_flairs/dentist.jpg differ
diff --git a/app/static/event_flairs/drank.jpg b/app/static/event_flairs/drank.jpg
new file mode 100644
index 00000000..517ab704
Binary files /dev/null and b/app/static/event_flairs/drank.jpg differ
diff --git a/app/static/event_flairs/food.jpg b/app/static/event_flairs/food.jpg
new file mode 100644
index 00000000..80a39832
Binary files /dev/null and b/app/static/event_flairs/food.jpg differ
diff --git a/app/static/event_flairs/golf.jpg b/app/static/event_flairs/golf.jpg
new file mode 100644
index 00000000..2d787446
Binary files /dev/null and b/app/static/event_flairs/golf.jpg differ
diff --git a/app/static/event_flairs/graduate.jpg b/app/static/event_flairs/graduate.jpg
new file mode 100644
index 00000000..b3820132
Binary files /dev/null and b/app/static/event_flairs/graduate.jpg differ
diff --git a/app/static/event_flairs/gym.jpg b/app/static/event_flairs/gym.jpg
new file mode 100644
index 00000000..0ee0f8cd
Binary files /dev/null and b/app/static/event_flairs/gym.jpg differ
diff --git a/app/static/event_flairs/haircut.jpg b/app/static/event_flairs/haircut.jpg
new file mode 100644
index 00000000..b7ec8c32
Binary files /dev/null and b/app/static/event_flairs/haircut.jpg differ
diff --git a/app/static/event_flairs/halloween.jpg b/app/static/event_flairs/halloween.jpg
new file mode 100644
index 00000000..24aed91f
Binary files /dev/null and b/app/static/event_flairs/halloween.jpg differ
diff --git a/app/static/event_flairs/hike.jpg b/app/static/event_flairs/hike.jpg
new file mode 100644
index 00000000..183fafc1
Binary files /dev/null and b/app/static/event_flairs/hike.jpg differ
diff --git a/app/static/event_flairs/kayak.jpg b/app/static/event_flairs/kayak.jpg
new file mode 100644
index 00000000..abcd0e6e
Binary files /dev/null and b/app/static/event_flairs/kayak.jpg differ
diff --git a/app/static/event_flairs/manicure.jpg b/app/static/event_flairs/manicure.jpg
new file mode 100644
index 00000000..62513be8
Binary files /dev/null and b/app/static/event_flairs/manicure.jpg differ
diff --git a/app/static/event_flairs/massage.jpg b/app/static/event_flairs/massage.jpg
new file mode 100644
index 00000000..db95454d
Binary files /dev/null and b/app/static/event_flairs/massage.jpg differ
diff --git a/app/static/event_flairs/music.jpg b/app/static/event_flairs/music.jpg
new file mode 100644
index 00000000..5a722d93
Binary files /dev/null and b/app/static/event_flairs/music.jpg differ
diff --git a/app/static/event_flairs/pill.jpg b/app/static/event_flairs/pill.jpg
new file mode 100644
index 00000000..71ae31b1
Binary files /dev/null and b/app/static/event_flairs/pill.jpg differ
diff --git a/app/static/event_flairs/pingpong.jpg b/app/static/event_flairs/pingpong.jpg
new file mode 100644
index 00000000..47a4dd66
Binary files /dev/null and b/app/static/event_flairs/pingpong.jpg differ
diff --git a/app/static/event_flairs/plan.jpg b/app/static/event_flairs/plan.jpg
new file mode 100644
index 00000000..34a9c009
Binary files /dev/null and b/app/static/event_flairs/plan.jpg differ
diff --git a/app/static/event_flairs/pokemon.jpg b/app/static/event_flairs/pokemon.jpg
new file mode 100644
index 00000000..9ddda581
Binary files /dev/null and b/app/static/event_flairs/pokemon.jpg differ
diff --git a/app/static/event_flairs/ran.jpg b/app/static/event_flairs/ran.jpg
new file mode 100644
index 00000000..e2ad3e06
Binary files /dev/null and b/app/static/event_flairs/ran.jpg differ
diff --git a/app/static/event_flairs/read.jpg b/app/static/event_flairs/read.jpg
new file mode 100644
index 00000000..cb66e0d7
Binary files /dev/null and b/app/static/event_flairs/read.jpg differ
diff --git a/app/static/event_flairs/repair.jpg b/app/static/event_flairs/repair.jpg
new file mode 100644
index 00000000..59731a10
Binary files /dev/null and b/app/static/event_flairs/repair.jpg differ
diff --git a/app/static/event_flairs/sail.jpg b/app/static/event_flairs/sail.jpg
new file mode 100644
index 00000000..00c6fba5
Binary files /dev/null and b/app/static/event_flairs/sail.jpg differ
diff --git a/app/static/event_flairs/santa.jpg b/app/static/event_flairs/santa.jpg
new file mode 100644
index 00000000..6b5a8794
Binary files /dev/null and b/app/static/event_flairs/santa.jpg differ
diff --git a/app/static/event_flairs/ski.jpg b/app/static/event_flairs/ski.jpg
new file mode 100644
index 00000000..dae2fa32
Binary files /dev/null and b/app/static/event_flairs/ski.jpg differ
diff --git a/app/static/event_flairs/soccer.jpg b/app/static/event_flairs/soccer.jpg
new file mode 100644
index 00000000..31de5b38
Binary files /dev/null and b/app/static/event_flairs/soccer.jpg differ
diff --git a/app/static/event_flairs/swam.jpg b/app/static/event_flairs/swam.jpg
new file mode 100644
index 00000000..04aba94b
Binary files /dev/null and b/app/static/event_flairs/swam.jpg differ
diff --git a/app/static/event_flairs/tennis.jpg b/app/static/event_flairs/tennis.jpg
new file mode 100644
index 00000000..cc015542
Binary files /dev/null and b/app/static/event_flairs/tennis.jpg differ
diff --git a/app/static/event_flairs/thanksgiving.jpg b/app/static/event_flairs/thanksgiving.jpg
new file mode 100644
index 00000000..25dff4b2
Binary files /dev/null and b/app/static/event_flairs/thanksgiving.jpg differ
diff --git a/app/static/event_flairs/wed.jpg b/app/static/event_flairs/wed.jpg
new file mode 100644
index 00000000..61fe9559
Binary files /dev/null and b/app/static/event_flairs/wed.jpg differ
diff --git a/app/static/event_flairs/yoga.jpg b/app/static/event_flairs/yoga.jpg
new file mode 100644
index 00000000..a0993c5b
Binary files /dev/null and b/app/static/event_flairs/yoga.jpg differ
diff --git a/requirements.txt b/requirements.txt
index ba9af619..dc96da2b 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,30 +1,45 @@
 aiofiles==0.6.0
+aioredis==1.3.1
+aiosmtpd==1.2.2
+aiosmtplib==1.1.4
 apipkg==1.5
 arrow==0.17.0
+async-timeout==3.0.1
 atomicwrites==1.4.0
+atpublic==2.1.2
 attrs==20.3.0
 beautifulsoup4==4.9.3
+blinker==1.4
 certifi==2020.12.5
 chardet==4.0.0
 click==7.1.2
 colorama==0.4.4
 coverage==5.3.1
+dnspython==2.1.0
+email-validator==1.1.2
 execnet==1.7.1
+Faker==5.6.2
+fakeredis==1.4.5
 fastapi==0.63.0
-fastapi_mail==0.3.3.1
-faker==5.6.2
+fastapi-mail==0.3.3.1
 frozendict==1.2
-smtpdfix==0.2.6
 h11==0.12.0
 h2==4.0.0
+hiredis==1.1.0
 hpack==4.0.0
+httpcore==0.12.2
+httpx==0.16.1
 hyperframe==6.0.0
 icalendar==4.0.7
 idna==2.10
 importlib-metadata==3.3.0
+inflect==4.1.0
 iniconfig==1.1.1
 Jinja2==2.11.2
+joblib==1.0.0
+lazy-object-proxy==1.5.2
 MarkupSafe==1.1.1
+nltk==3.5
 packaging==20.8
 Pillow==8.1.0
 pluggy==0.13.1
@@ -42,18 +57,27 @@ python-dotenv==0.15.0
 python-multipart==0.0.5
 pytz==2020.5
 PyYAML==5.3.1
+redis==3.5.3
+regex==2020.11.13
 requests==2.25.1
 requests-mock==1.8.0
 responses==0.12.1
+rfc3986==1.4.0
 six==1.15.0
+smtpdfix==0.2.6
+sniffio==1.2.0
+sortedcontainers==2.3.0
 soupsieve==2.1
 SQLAlchemy==1.3.22
 starlette==0.13.6
+text-unidecode==1.3
 toml==0.10.2
+tqdm==4.56.0
 typing-extensions==3.7.4.3
 urllib3==1.26.2
 uvicorn==0.13.3
 watchgod==0.6
 websockets==8.1
+word-forms==2.1.0
 wsproto==1.0.0
 zipp==3.4.0
diff --git a/tests/test_event_images.py b/tests/test_event_images.py
new file mode 100644
index 00000000..ba7df635
--- /dev/null
+++ b/tests/test_event_images.py
@@ -0,0 +1,77 @@
+from app.routers.event_images import attach_image_to_event,\
+    generate_flare_link_from_lemmatized_word, get_image_name,\
+    remove_non_alphabet_chars, search_token_in_related_words
+from app import config
+import pytest
+
+
+static = config.STATIC_ABS_PATH
+
+
+lemmatized_words = [
+    ("ran",  f'{static}\\event_flairs\\ran.jpg'),
+    ("food", f'{static}\\event_flairs\\food.jpg'),
+    ("i",  f'{static}\\event_flairs\\i.jpg'),
+    ("drank", f'{static}\\event_flairs\\drank.jpg'),
+]
+
+
+@pytest.mark.parametrize('lemmatized, link', lemmatized_words)
+def test_generate_flare_link_from_lemmatized_word(lemmatized, link):
+    assert generate_flare_link_from_lemmatized_word(lemmatized) == link
+
+
+contents = [
+    (r"it's my birthday!", r"itsmybirthday"),
+    (r"iT's   my birthday!!!", r"iTsmybirthday"),
+    (r"its my birthday", r"itsmybirthday"),
+    (r"it's-my-birthday!1990", r"itsmybirthday"),
+]
+
+
+@pytest.mark.parametrize('content, alphabet_only', contents)
+def test_remove_non_alphabet_chars(content, alphabet_only):
+    assert remove_non_alphabet_chars(content) == alphabet_only
+
+
+values = [
+    (r"backrub", r"massage"),
+    (r"--MedicineS", r"pill"),
+    (r"restaurants", r"food"),
+    (r"pikachu", None),
+    (r"Pokemon", r"pokemon"),
+]
+
+
+@pytest.mark.parametrize('related_word, key', values)
+def test_get_image_name(related_word, key):
+    assert get_image_name(related_word) == key
+
+
+tokens = [
+    (r"backrub", f'{static}\\event_flairs\\massage.jpg'),
+    (r"--MedicineS", f'{static}\\event_flairs\\pill.jpg'),
+    (r"restaurants", f'{static}\\event_flairs\\food.jpg'),
+    (r"pikachu", None),
+    (r"Pokemon", f'{static}\\event_flairs\\pokemon.jpg'),
+]
+
+
+@pytest.mark.parametrize('token, link', tokens)
+def test_search_token_in_related_words(token, link):
+    assert search_token_in_related_words(token) == link
+
+
+event_contents = [
+    (r"memo backrub and medicines!!", f'{static}\\event_flairs\\massage.jpg'),
+    (r"Dont forget medicines & backrub!", f'{static}\\event_flairs\\pill.jpg'),
+    (r"Its important to drink", f'{static}\\event_flairs\\drank.jpg'),
+    (r"call Jim about tennis friday", f'{static}\\event_flairs\\tennis.jpg'),
+    (r"have to check on pikachu", r'#'),
+    (r"-~new pokemon episode 19:00~!", f'{static}\\event_flairs\\pokemon.jpg'),
+]
+
+
+@pytest.mark.parametrize('event_content, link', event_contents)
+def test_attach_image_to_event(event_content, link):
+    assert attach_image_to_event(event_content) == link