diff --git a/src/parser/list.rs b/src/parser/list.rs
index e15e8da2..d976f625 100644
--- a/src/parser/list.rs
+++ b/src/parser/list.rs
@@ -20,6 +20,12 @@ pub struct Node<T> {
     parent: Option<Rc<Node<T>>>,
 }
 
+impl<T> Node<T> {
+    pub fn get_data(&self) -> &T {
+        &self.data
+    }
+}
+
 // TODO: This Debug is only needed because of the try_unwrap+expect
 impl<T: Debug> List<T> {
     pub fn new() -> Self {
@@ -72,6 +78,12 @@ impl<T: Debug> List<T> {
             (Some(me), Some(them)) => Rc::ptr_eq(me, them),
         }
     }
+
+    pub fn iter(&self) -> impl Iterator<Item = &Rc<Node<T>>> {
+        NodeIter {
+            position: &self.head,
+        }
+    }
 }
 
 pub struct NodeIter<'a, T> {
diff --git a/src/parser/nom_context.rs b/src/parser/nom_context.rs
index 5fa6f978..e1bc2beb 100644
--- a/src/parser/nom_context.rs
+++ b/src/parser/nom_context.rs
@@ -1,9 +1,12 @@
+use std::rc::Rc;
+
 use nom::bytes::complete::take;
 use nom::combinator::not;
 use nom::error::VerboseError;
 use nom::IResult;
 
 use super::list::List;
+use super::list::Node;
 use super::token::Token;
 
 type Matcher = dyn for<'s> Fn(&'s str) -> IResult<&'s str, &'s str, VerboseError<&'s str>>;
@@ -32,6 +35,10 @@ impl<'r, 's> ContextTree<'r, 's> {
         (popped_element, ContextTree { tree: remaining })
     }
 
+    pub fn iter(&self) -> impl Iterator<Item = &Rc<Node<ContextElement<'r, 's>>>> {
+        self.tree.iter()
+    }
+
     pub fn check_fail_matcher<'b>(
         &'r self,
         i: &'b str,
diff --git a/src/parser/text_element_parser.rs b/src/parser/text_element_parser.rs
index 5ba26c54..c0eae4ea 100644
--- a/src/parser/text_element_parser.rs
+++ b/src/parser/text_element_parser.rs
@@ -22,6 +22,8 @@ use super::text::TextElement;
 use super::token::Token;
 use super::Context;
 use nom::branch::alt;
+use nom::bytes::complete::take;
+use nom::combinator::cond;
 use nom::combinator::eof;
 use nom::combinator::map;
 use nom::combinator::not;
@@ -118,11 +120,49 @@ pub fn context_paragraph_end<'s, 'r>(
     paragraph_end(input)
 }
 
+fn can_start_bold<'s, 'r>(context: Context<'r, 's>) -> bool {
+    let mut context_iterator = context.iter().enumerate();
+    loop {
+        if let Some((i, ctx)) = context_iterator.next() {
+            match ctx.get_data() {
+                ContextElement::FailMatcherNode(_) => {},
+                ContextElement::PreviousElementNode(previous_element_node) => {
+                    // TODO okay if previous element is a space but not if its text
+                    match &previous_element_node.element {
+                        Token::TextElement(text_element) => {
+                            match text_element {
+                                TextElement::Span(_) => return false,
+                                TextElement::Space(_) => return true,
+                                TextElement::LineBreak(_) => return true,
+                                TextElement::Symbol(_) => return false,
+                                TextElement::Bold(_) => return false,
+                                TextElement::Link(_) => return false,
+                            };
+                        },
+                    };
+                },
+                ContextElement::StartOfParagraph => {
+                    return true;
+                },
+            }
+        } else {
+            break;
+        }
+    }
+    false
+}
+
 pub fn context_bold_start<'s, 'r>(
     context: Context<'r, 's>,
     input: &'s str,
 ) -> Res<&'s str, &'s str> {
-    recognize(bold_start)(input)
+    if can_start_bold(context) {
+        recognize(bold_start)(input)
+    } else {
+        // TODO: Make this a custom error
+        not(take(0usize))(input)?;
+        unreachable!()
+    }
 }
 
 pub fn context_bold_end<'s, 'r>(context: Context<'r, 's>, input: &'s str) -> Res<&'s str, &'s str> {