diff --git a/helix-term/src/ui/mod.rs b/helix-term/src/ui/mod.rs
index a76adbe21..1e5fa2c4c 100644
--- a/helix-term/src/ui/mod.rs
+++ b/helix-term/src/ui/mod.rs
@@ -32,6 +32,7 @@ pub use text::Text;
 use helix_view::Editor;
 use tui::text::{Span, Spans};
 
+use std::borrow::Cow;
 use std::path::Path;
 use std::{error::Error, path::PathBuf};
 
@@ -185,6 +186,23 @@ pub fn raw_regex_prompt(
     cx.push_layer(Box::new(prompt));
 }
 
+/// Get the relative directory as a string.
+///
+/// NOTE: Assumes the given path is a directory, and will always output wiht a
+/// trailing slash.
+fn get_relative_dir(path: &Path) -> Cow<'static, str> {
+    let path = helix_stdx::path::get_relative_path(path);
+    if path.components().next().is_none() {
+        "./".into()
+    } else {
+        let mut str = path.to_string_lossy().into_owned();
+        if !str.ends_with('/') {
+            str.push('/');
+        }
+        str.into()
+    }
+}
+
 #[derive(Debug)]
 pub struct FilePickerData {
     root: PathBuf,
@@ -246,7 +264,7 @@ pub fn file_picker(editor: &Editor, root: PathBuf) -> FilePicker {
     log::debug!("file_picker init {:?}", Instant::now().duration_since(now));
 
     let columns = [PickerColumn::new(
-        "path",
+        get_relative_dir(&root),
         |item: &PathBuf, data: &FilePickerData| {
             let path = item.strip_prefix(&data.root).unwrap_or(item);
             let mut spans = Vec::with_capacity(3);
@@ -274,6 +292,7 @@ pub fn file_picker(editor: &Editor, root: PathBuf) -> FilePicker {
             cx.editor.set_error(err);
         }
     })
+    .always_show_headers()
     .with_preview(|_editor, path| Some((path.as_path().into(), None)));
     let injector = picker.injector();
     let timeout = std::time::Instant::now() + std::time::Duration::from_millis(30);
@@ -307,7 +326,7 @@ pub fn file_explorer(root: PathBuf, editor: &Editor) -> Result<FileExplorer, std
     let directory_content = directory_content(&root)?;
 
     let columns = [PickerColumn::new(
-        "path",
+        get_relative_dir(&root),
         |(path, is_dir): &(PathBuf, bool), (root, directory_style): &(PathBuf, Style)| {
             let name = path.strip_prefix(root).unwrap_or(path).to_string_lossy();
             if *is_dir {
@@ -345,6 +364,7 @@ pub fn file_explorer(root: PathBuf, editor: &Editor) -> Result<FileExplorer, std
             }
         },
     )
+    .always_show_headers()
     .with_preview(|_editor, (path, _is_dir)| Some((path.as_path().into(), None)));
 
     Ok(picker)
diff --git a/helix-term/src/ui/picker.rs b/helix-term/src/ui/picker.rs
index a6ce91a67..00357368c 100644
--- a/helix-term/src/ui/picker.rs
+++ b/helix-term/src/ui/picker.rs
@@ -241,6 +241,7 @@ type DynQueryCallback<T, D> =
 pub struct Picker<T: 'static + Send + Sync, D: 'static> {
     columns: Arc<[Column<T, D>]>,
     primary_column: usize,
+    always_show_headers: bool,
     editor_data: Arc<D>,
     version: Arc<AtomicUsize>,
     matcher: Nucleo<T>,
@@ -373,6 +374,7 @@ impl<T: 'static + Send + Sync, D: 'static + Send + Sync> Picker<T, D> {
         Self {
             columns,
             primary_column: default_column,
+            always_show_headers: false,
             matcher,
             editor_data,
             version,
@@ -424,6 +426,11 @@ impl<T: 'static + Send + Sync, D: 'static + Send + Sync> Picker<T, D> {
         self
     }
 
+    pub fn always_show_headers(mut self) -> Self {
+        self.always_show_headers = true;
+        self
+    }
+
     pub fn with_dynamic_query(
         mut self,
         callback: DynQueryCallback<T, D>,
@@ -818,7 +825,7 @@ impl<T: 'static + Send + Sync, D: 'static + Send + Sync> Picker<T, D> {
             .widths(&self.widths);
 
         // -- Header
-        if self.columns.len() > 1 {
+        if self.always_show_headers || self.columns.len() > 1 {
             let active_column = self.query.active_column(self.prompt.position());
             let header_style = cx.editor.theme.get("ui.picker.header");
             let header_column_style = cx.editor.theme.get("ui.picker.header.column");