diff --git a/convokit/open_question/__init.__.py b/convokit/open_question/__init.__.py
new file mode 100644
index 00000000..67a1ab81
--- /dev/null
+++ b/convokit/open_question/__init.__.py
@@ -0,0 +1,2 @@
+from .opennessScoreBERT import *
+from .opennessScoreSimilarity import *
diff --git a/convokit/open_question/opennessScoreBERT.py b/convokit/open_question/opennessScoreBERT.py
new file mode 100644
index 00000000..cc8bc845
--- /dev/null
+++ b/convokit/open_question/opennessScoreBERT.py
@@ -0,0 +1,179 @@
+import convokit
+from convokit import Corpus, download, FightingWords
+from convokit.transformer import Transformer
+from inspect import signature
+from collections import defaultdict
+from itertools import permutations
+from nltk.tokenize import word_tokenize
+from convokit import Corpus, download
+import matplotlib.pyplot as plt
+import numpy as np
+import random
+from transformers import AutoModelForMaskedLM, AutoTokenizer
+import torch
+import language_tool_python
+import os
+
+
+class OpennessScoreBERT(Transformer):
+    """
+    A transformer to calculate openness score for all utterance
+
+    :param obj_type: type of Corpus object to calculate: 'conversation', 'speaker', or 'utterance', default to be 'utterance'
+    :param input_field: Input fields from every utterance object. Will default to reading 'utt.text'. If a string is provided, than consider metadata with field name input_field.
+    :param output_field: field for writing the computed output in metadata. Will default to write to utterance metadata with name 'capitalization'.
+    :param input_filter: a boolean function of signature `input_filter(utterance, aux_input)`. attributes will only be computed for utterances where `input_filter` returns `True`. By default, will always return `True`, meaning that attributes will be computed for all utterances.
+    :param verbosity: frequency at which to print status messages when computing attributes.
+    """
+
+    def __init__(
+        self,
+        obj_type="utterance",
+        output_field="openness_score",
+        input_field=None,
+        input_filter=None,
+        model_name="bert-base-cased",
+        verbosity=1000,
+    ):
+        if input_filter:
+            if len(signature(input_filter).parameters) == 1:
+                self.input_filter = lambda utt: input_filter(utt)
+            else:
+                self.input_filter = input_filter
+        else:
+            self.input_filter = lambda utt: True
+        self.obj_type = obj_type
+        self.input_field = input_field
+        self.output_field = output_field
+        self.verbosity = verbosity
+        self.grammar_tool = language_tool_python.LanguageToolPublicAPI("en")
+        self.answer_sample = ["Mhm", "Okay", "I see", "Yup"]
+        self.model = AutoModelForMaskedLM.from_pretrained(model_name)
+        self.tokenizer = AutoTokenizer.from_pretrained(model_name)
+
+    def _print_output(self, i):
+        return (self.verbosity > 0) and (i > 0) and (i % self.verbosity == 0)
+
+    def bert_score(self, question, answer):
+        """
+        Outputs the perplexitty score for predicting the answer, given the question
+
+        :param question: str
+        :param answer: str
+        :return: perplexity
+        """
+        sentence = question + " " + answer
+        tensor_input = self.tokenizer.encode(sentence, return_tensors="pt")
+        question_tok_len = len(self.tokenizer.encode(question)) - 2
+        repeat_input = tensor_input.repeat(tensor_input.size(-1) - 2 - question_tok_len, 1)
+        mask = torch.ones(tensor_input.size(-1) - 1).diag(1)[:-2][question_tok_len:]
+        masked_input = repeat_input.masked_fill(mask == 1, self.tokenizer.mask_token_id)
+        labels = repeat_input.masked_fill(masked_input != self.tokenizer.mask_token_id, -100)
+        with torch.inference_mode():
+            loss = self.model(masked_input, labels=labels).loss
+        return np.exp(loss.item())
+
+    def find_last_question(self, text):
+        """
+        Finds the last sentence that ended with a question mark
+
+        :param text: str
+        :return: text
+        """
+        end_sent = set([".", "?", "!"])
+        last_q = text.rfind("?")
+        for i in range(last_q - 1, -1, -1):
+            if text[i] in end_sent:
+                return text[i + 1 : last_q + 1].strip()
+        return text[: last_q + 1].strip()
+
+    def bert_opennes_score(self, question):
+        scores = []
+        question = self.find_last_question(question)
+        question = self.grammar_tool.correct(question)
+
+        for ans in self.answer_sample:
+            ans_text = ans
+            perp = self.bert_score(question, ans_text)
+            scores.append(perp)
+        return np.mean(scores)
+
+    def transform(self, corpus: Corpus) -> Corpus:
+        """
+        Score the given utterance on their openness and store it to the corresponding object metadata fields.
+
+        :param corpus: Corpus
+        :return: the corpus
+        """
+        if self.obj_type == "utterance":
+            total = len(list(corpus.iter_utterances()))
+
+            for idx, utterance in enumerate(corpus.iter_utterances()):
+                if self._print_output(idx):
+                    print(f"%03d/%03d {self.obj_type} processed" % (idx, total))
+
+                if not self.input_filter(utterance):
+                    continue
+
+                if self.input_field is None:
+                    text_entry = utterance.text
+                elif isinstance(self.input_field, str):
+                    text_entry = utterance.meta(self.input_field)
+                if text_entry is None:
+                    continue
+
+                # do the catching and add to output_field
+                catch = self.bert_opennes_score(text_entry)
+
+                utterance.add_meta(self.output_field, catch)
+
+        elif self.obj_type == "conversation":
+            total = len(list(corpus.iter_conversations()))
+            for idx, convo in enumerate(corpus.iter_conversations()):
+                if self._print_output(idx):
+                    print(f"%03d/%03d {self.obj_type} processed" % (idx, total))
+
+                if not self.input_filter(convo):
+                    continue
+
+                if self.input_field is None:
+                    utt_lst = convo.get_utterance_ids()
+                    text_entry = " ".join([corpus.get_utterance(x).text for x in utt_lst])
+                elif isinstance(self.input_field, str):
+                    text_entry = convo.meta(self.input_field)
+                if text_entry is None:
+                    continue
+
+                # do the catching and add to output_field
+                catch = self.bert_opennes_score(text_entry)
+
+                convo.add_meta(self.output_field, catch)
+
+        elif self.obj_type == "speaker":
+            total = len(list(corpus.iter_speakers()))
+            for idx, sp in enumerate(corpus.iter_speakers()):
+                if self._print_output(idx):
+                    print(f"%03d/%03d {self.obj_type} processed" % (idx, total))
+
+                if not self.input_filter(sp):
+                    continue
+
+                if self.input_field is None:
+                    utt_lst = sp.get_utterance_ids()
+                    text_entry = " ".join([corpus.get_utterance(x).text for x in utt_lst])
+                elif isinstance(self.input_field, str):
+                    text_entry = sp.meta(self.input_field)
+                if text_entry is None:
+                    continue
+
+                # do the catching and add to output_field
+                catch = self.bert_opennes_score(text_entry)
+
+                sp.add_meta(self.output_field, catch)
+
+        else:
+            raise KeyError("obj_type must be utterance, conversation, or speaker")
+
+        if self.verbosity > 0:
+            print(f"%03d/%03d {self.obj_type} processed" % (total, total))
+        return corpus
diff --git a/convokit/open_question/opennessScoreSimilarity.py b/convokit/open_question/opennessScoreSimilarity.py
new file mode 100644
index 00000000..e38d407f
--- /dev/null
+++ b/convokit/open_question/opennessScoreSimilarity.py
@@ -0,0 +1,199 @@
+from convokit import Corpus, download, FightingWords
+from convokit.transformer import Transformer
+from inspect import signature
+from collections import defaultdict
+from itertools import permutations
+from nltk.tokenize import word_tokenize
+from convokit import Corpus, download
+import matplotlib.pyplot as plt
+import numpy as np
+import random
+from sentence_transformers import SentenceTransformer, util
+from haystack.document_stores import InMemoryDocumentStore
+from haystack.nodes import BM25Retriever
+from haystack.pipelines import DocumentSearchPipeline
+import language_tool_python
+
+
+class OpennessScoreSimilarity(Transformer):
+    """
+    A transformer that uses BERT similarity to calculate openness score
+
+    :param obj_type: type of Corpus object to calculate: 'conversation', 'speaker', or 'utterance', default to be 'utterance'
+    :param input_field: Input fields from every utterance object. Will default to reading 'utt.text'. If a string is provided, than consider metadata with field name input_field.
+    :param output_field: field for writing the computed output in metadata. Will default to write to utterance metadata with name 'capitalization'.
+    :param input_filter: a boolean function of signature `input_filter(utterance, aux_input)`. attributes will only be computed for utterances where `input_filter` returns `True`. By default, will always return `True`, meaning that attributes will be computed for all utterances.
+    :param verbosity: frequency at which to print status messages when computing attributes.
+    """
+
+    def __init__(
+        self,
+        obj_type="utterance",
+        output_field="openness_score",
+        input_field=None,
+        input_filter=None,
+        model_name="bert-base-cased",
+        verbosity=1000,
+    ):
+        if input_filter:
+            if len(signature(input_filter).parameters) == 1:
+                self.input_filter = lambda utt: input_filter(utt)
+            else:
+                self.input_filter = input_filter
+        else:
+            self.input_filter = lambda utt: True
+        self.obj_type = obj_type
+        self.input_field = input_field
+        self.output_field = output_field
+        self.verbosity = verbosity
+        self.grammar_tool = language_tool_python.LanguageToolPublicAPI("en")
+        self.answer_sample = ["Mhm", "Okay", "I see", "Yup"]
+        self.document_store = InMemoryDocumentStore(use_bm25=True)
+        self.model = SentenceTransformer("multi-qa-MiniLM-L6-cos-v1", device="cpu")  # SBERT model
+
+    def fit(self, corpus: Corpus, y=None):
+        """Learn context information for the given corpus."""
+        self.corpus = corpus
+        self._load_questions(corpus)
+
+    def _print_output(self, i):
+        return (self.verbosity > 0) and (i > 0) and (i % self.verbosity == 0)
+
+    def generated_openness_score_similarity(self, text):
+        if len(text) > 500 and len(word_tokenize(text)) > 100:
+            text_token = word_tokenize(self._find_last_question(text))
+            text = ""
+            for token in text:
+                text = text + " " + token
+        prediction = self.pipe.run(query=text, params={"Retriever": {"top_k": 10}})
+        answers = [prediction["documents"][i].meta["answer"] for i in range(10)]
+        return self._avg_bert_sim(answers)
+
+    def transform(self, corpus: Corpus) -> Corpus:
+        """
+        Score the given utterance on their openness and store it to the corresponding object metadata fields.
+
+        :param corpus: Corpus
+        :return: the corpus
+        """
+        if self.obj_type == "utterance":
+            total = len(list(corpus.iter_utterances()))
+
+            for idx, utterance in enumerate(corpus.iter_utterances()):
+                if self._print_output(idx):
+                    print(f"%03d/%03d {self.obj_type} processed" % (idx, total))
+
+                if not self.input_filter(utterance):
+                    continue
+
+                if self.input_field is None:
+                    text_entry = utterance.text
+                elif isinstance(self.input_field, str):
+                    text_entry = utterance.meta(self.input_field)
+                if text_entry is None:
+                    continue
+
+                # do the catching and add to output_field
+                catch = self.generated_openness_score_similarity(text_entry)
+
+                utterance.add_meta(self.output_field, catch)
+
+        elif self.obj_type == "conversation":
+            total = len(list(corpus.iter_conversations()))
+            for idx, convo in enumerate(corpus.iter_conversations()):
+                if self._print_output(idx):
+                    print(f"%03d/%03d {self.obj_type} processed" % (idx, total))
+
+                if not self.input_filter(convo):
+                    continue
+
+                if self.input_field is None:
+                    utt_lst = convo.get_utterance_ids()
+                    text_entry = " ".join([corpus.get_utterance(x).text for x in utt_lst])
+                elif isinstance(self.input_field, str):
+                    text_entry = convo.meta(self.input_field)
+                if text_entry is None:
+                    continue
+
+                # do the catching and add to output_field
+                catch = self.generated_openness_score_similarity(text_entry)
+
+                convo.add_meta(self.output_field, catch)
+
+        elif self.obj_type == "speaker":
+            total = len(list(corpus.iter_speakers()))
+            for idx, sp in enumerate(corpus.iter_speakers()):
+                if self._print_output(idx):
+                    print(f"%03d/%03d {self.obj_type} processed" % (idx, total))
+
+                if not self.input_filter(sp):
+                    continue
+
+                if self.input_field is None:
+                    utt_lst = sp.get_utterance_ids()
+                    text_entry = " ".join([corpus.get_utterance(x).text for x in utt_lst])
+                elif isinstance(self.input_field, str):
+                    text_entry = sp.meta(self.input_field)
+                if text_entry is None:
+                    continue
+
+                # do the catching and add to output_field
+                catch = self.generated_openness_score_similarity(text_entry)
+
+                sp.add_meta(self.output_field, catch)
+
+        else:
+            raise KeyError("obj_type must be utterance, conversation, or speaker")
+
+        if self.verbosity > 0:
+            print(f"%03d/%03d {self.obj_type} processed" % (total, total))
+        return corpus
+
+    # helper function
+    def _load_questions(self, corpus):
+        """"""
+        docs = []
+        convo_ids = corpus.get_conversation_ids()
+        for idx in convo_ids:
+            convo = corpus.get_conversation(idx)
+            utts = convo.get_chronological_utterance_list()
+            had_question = False
+            before_text = ""
+            for utt in utts:
+                if had_question:
+                    dic_transf = {
+                        "content": before_text,
+                        "meta": {"convo_id": idx, "answer": utt.text},
+                    }
+                    docs.append(dic_transf)
+                    had_question = False
+                if utt.meta["questions"] > 0:
+                    had_question = True
+                    before_text = utt.text
+        self.document_store.write_documents(docs)
+        self.retriever = BM25Retriever(document_store=self.document_store)
+        self.pipe = DocumentSearchPipeline(retriever=self.retriever)
+
+    def _sbert_embedd_sim(self, embedding1, embedding2):
+        return float(util.cos_sim(embedding1, embedding2))
+
+    def _avg_bert_sim(self, texts):
+        embeddings = []
+        for text in texts:
+            embeddings.append(self.model.encode(text))
+
+        scores = []
+        for i, embedding1 in enumerate(embeddings):
+            for j, embedding2 in enumerate(embeddings):
+                if i >= j:
+                    continue
+                scores.append(self._sbert_embedd_sim(embedding1, embedding2))
+        return np.mean(scores)
+
+    def _find_last_question(self, text):
+        end_sent = set([".", "?", "!"])
+        last_q = text.rfind("?")
+        for i in range(last_q - 1, -1, -1):
+            if text[i] in end_sent:
+                return text[i + 1 : last_q + 1].strip()
+        return text[: last_q + 1].strip()
diff --git a/examples/open_question/open_question_bert_demo.ipynb b/examples/open_question/open_question_bert_demo.ipynb
new file mode 100644
index 00000000..8a4998e9
--- /dev/null
+++ b/examples/open_question/open_question_bert_demo.ipynb
@@ -0,0 +1,113 @@
+{
+ "cells": [
+  {
+   "cell_type": "code",
+   "execution_count": null,
+   "metadata": {},
+   "outputs": [],
+   "source": [
+    "# Importing neccesary packages\n",
+    "import convokit\n",
+    "from convokit import Corpus, OpennessScoreSimilarity\n",
+    "from tqdm import tqdm\n",
+    "import matplotlib.pyplot as plt\n",
+    "import random\n",
+    "from convokit import Corpus\n"
+   ]
+  },
+  {
+   "cell_type": "code",
+   "execution_count": null,
+   "metadata": {},
+   "outputs": [],
+   "source": [
+    "#Load the CANDOR CORPUS\n",
+    "data_dir = \"Directory\"\n",
+    "corpus = Corpus(filename=data_dir)"
+   ]
+  },
+  {
+   "cell_type": "code",
+   "execution_count": null,
+   "metadata": {},
+   "outputs": [],
+   "source": [
+    "#Sample 100 random conversations to compute\n",
+    "random.seed(4350)\n",
+    "random_convo = random.sample(corpus.get_conversation_ids(), 100)\n",
+    "convo_ids = corpus.get_conversation_ids()\n",
+    "for idx in tqdm(convo_ids):\n",
+    "  convo = corpus.get_conversation(idx)\n",
+    "  utts = convo.get_chronological_utterance_list()\n",
+    "  for utt in utts:\n",
+    "    utt.meta['sample'] = False\n",
+    "\n",
+    "for idx in tqdm(random_convo):\n",
+    "  convo = corpus.get_conversation(idx)\n",
+    "  utts = convo.get_chronological_utterance_list()\n",
+    "  for utt in utts:\n",
+    "    if utt.meta['questions'] > 0:\n",
+    "      utt.meta['sample'] = True"
+   ]
+  },
+  {
+   "cell_type": "code",
+   "execution_count": null,
+   "metadata": {},
+   "outputs": [],
+   "source": [
+    "#Run the transformer\n",
+    "open_scorer = OpennessScoreSimilarity(input_filter = lambda utt: utt.meta['sample'])\n",
+    "open_scorer.fit(corpus)\n",
+    "corpus = open_scorer.transform(corpus)"
+   ]
+  },
+  {
+   "cell_type": "code",
+   "execution_count": null,
+   "metadata": {},
+   "outputs": [],
+   "source": [
+    "#Print the most and least open questions\n",
+    "scores = []\n",
+    "questions = []\n",
+    "for idx in random_convo:\n",
+    "  convo = corpus.get_conversation(idx)\n",
+    "  utts = convo.get_chronological_utterance_list()\n",
+    "  for utt in utts:\n",
+    "    if utt.meta['sample']:\n",
+    "      scores.append(utt.meta['openness_score'])\n",
+    "      questions.append(utt.text)\n",
+    "\n",
+    "print(\"######## The Most Open Questions ########\")\n",
+    "arg_sort = np.argsort(scores)\n",
+    "for i in range(5):\n",
+    "  print(questions[arg_sort[i]])\n",
+    "print(\"######## The Most Closed Questions ########\")\n",
+    "for i in range(5):\n",
+    "  print(questions[arg_sort[-i]])"
+   ]
+  }
+ ],
+ "metadata": {
+  "kernelspec": {
+   "display_name": "cs4300",
+   "language": "python",
+   "name": "python3"
+  },
+  "language_info": {
+   "codemirror_mode": {
+    "name": "ipython",
+    "version": 3
+   },
+   "file_extension": ".py",
+   "mimetype": "text/x-python",
+   "name": "python",
+   "nbconvert_exporter": "python",
+   "pygments_lexer": "ipython3",
+   "version": "3.7.6"
+  }
+ },
+ "nbformat": 4,
+ "nbformat_minor": 2
+}