diff --git a/src/playlist/playlist.h b/src/playlist/playlist.h
index 2c1236bab..a3a80cbb7 100644
--- a/src/playlist/playlist.h
+++ b/src/playlist/playlist.h
@@ -138,6 +138,8 @@ class Playlist : public QAbstractListModel {
     Path_Automatic = 0,  // Automatically select path type
     Path_Absolute,       // Always use absolute paths
     Path_Relative,       // Always use relative paths
+    Path_Ask_User,       // Only used in preferences: to ask user which of the
+                         // previous values he wants to use.
   };
 
   static const char* kCddaMimeType;
diff --git a/src/playlist/playlistmanager.cpp b/src/playlist/playlistmanager.cpp
index 9ff41da8e..334d26c29 100644
--- a/src/playlist/playlistmanager.cpp
+++ b/src/playlist/playlistmanager.cpp
@@ -18,6 +18,7 @@
 #include "playlistbackend.h"
 #include "playlistcontainer.h"
 #include "playlistmanager.h"
+#include "playlistsaveoptionsdialog.h"
 #include "playlistview.h"
 #include "core/application.h"
 #include "core/logging.h"
@@ -172,9 +173,10 @@ void PlaylistManager::Load(const QString& filename) {
   playlist->InsertUrls(urls << QUrl::fromLocalFile(filename));
 }
 
-void PlaylistManager::Save(int id, const QString& filename) {
+void PlaylistManager::Save(int id, const QString& filename,
+                           Playlist::Path path_type) {
   if (playlists_.contains(id)) {
-    parser_->Save(playlist(id)->GetAllSongs(), filename);
+    parser_->Save(playlist(id)->GetAllSongs(), filename, path_type);
   } else {
     // Playlist is not in the playlist manager: probably save action was
     // triggered
@@ -184,16 +186,18 @@ void PlaylistManager::Save(int id, const QString& filename) {
     watcher->setFuture(future);
 
     NewClosure(watcher, SIGNAL(finished()), this,
-               SLOT(ItemsLoadedForSavePlaylist(QFutureWatcher<Song>*, QString)),
+               SLOT(ItemsLoadedForSavePlaylist(QFutureWatcher<Song>*, QString,
+                                               Playlist::Path)),
                watcher, filename);
   }
 }
 
 void PlaylistManager::ItemsLoadedForSavePlaylist(QFutureWatcher<Song>* watcher,
-                                                 const QString& filename) {
+                                                 const QString& filename,
+                                                 Playlist::Path path_type) {
 
   SongList song_list = watcher->future().results();
-  parser_->Save(song_list, filename);
+  parser_->Save(song_list, filename, path_type);
 }
 
 void PlaylistManager::SaveWithUI(int id, const QString& suggested_filename) {
@@ -230,10 +234,23 @@ void PlaylistManager::SaveWithUI(int id, const QString& suggested_filename) {
     return;
   }
 
+  QSettings s;
+  s.beginGroup(Playlist::kSettingsGroup);
+  int p = s.value(Playlist::kPathType, Playlist::Path_Automatic).toInt();
+  Playlist::Path path = static_cast<Playlist::Path>(p);
+  if (path == Playlist::Path_Ask_User) {
+    PlaylistSaveOptionsDialog optionsDialog(nullptr);
+    optionsDialog.setModal(true);
+    if (optionsDialog.exec() != QDialog::Accepted) {
+      return;
+    }
+    path = optionsDialog.path_type();
+  }
+
   settings.setValue("last_save_playlist", filename);
   settings.endGroup();
 
-  Save(id == -1 ? current_id() : id, filename);
+  Save(id == -1 ? current_id() : id, filename, path);
 }
 
 void PlaylistManager::Rename(int id, const QString& new_name) {
diff --git a/src/playlist/playlistmanager.h b/src/playlist/playlistmanager.h
index f516c3dc8..6f33bbb6f 100644
--- a/src/playlist/playlistmanager.h
+++ b/src/playlist/playlistmanager.h
@@ -76,7 +76,7 @@ class PlaylistManagerInterface : public QObject {
   virtual void New(const QString& name, const SongList& songs = SongList(),
                    const QString& special_type = QString()) = 0;
   virtual void Load(const QString& filename) = 0;
-  virtual void Save(int id, const QString& filename) = 0;
+  virtual void Save(int id, const QString& filename, Playlist::Path path_type) = 0;
   virtual void Rename(int id, const QString& new_name) = 0;
   virtual void Delete(int id) = 0;
   virtual bool Close(int id) = 0;
@@ -181,7 +181,7 @@ class PlaylistManager : public PlaylistManagerInterface {
   void New(const QString& name, const SongList& songs = SongList(),
            const QString& special_type = QString());
   void Load(const QString& filename);
-  void Save(int id, const QString& filename);
+  void Save(int id, const QString& filename, Playlist::Path path_type);
   // Display a file dialog to let user choose a file before saving the file
   void SaveWithUI(int id, const QString& suggested_filename);
   void Rename(int id, const QString& new_name);
@@ -232,7 +232,8 @@ class PlaylistManager : public PlaylistManagerInterface {
   void UpdateSummaryText();
   void SongsDiscovered(const SongList& songs);
   void ItemsLoadedForSavePlaylist(QFutureWatcher<Song>* watcher,
-                                  const QString& filename);
+                                  const QString& filename,
+                                  Playlist::Path path_type);
 
  private:
   Playlist* AddPlaylist(int id, const QString& name,
diff --git a/src/playlist/playlistsaveoptionsdialog.cpp b/src/playlist/playlistsaveoptionsdialog.cpp
index 44d0f9538..48bda0859 100644
--- a/src/playlist/playlistsaveoptionsdialog.cpp
+++ b/src/playlist/playlistsaveoptionsdialog.cpp
@@ -1,5 +1,5 @@
 /* This file is part of Clementine.
-   Copyright 2010, David Sansome <me@davidsansome.com>
+   Copyright 2014, David Sansome <me@davidsansome.com>
 
    Clementine is free software: you can redistribute it and/or modify
    it under the terms of the GNU General Public License as published by
@@ -29,44 +29,24 @@ PlaylistSaveOptionsDialog::PlaylistSaveOptionsDialog(QWidget* parent)
     : QDialog(parent), ui(new Ui::PlaylistSaveOptionsDialog) {
   ui->setupUi(this);
 
-  ui->filePaths->addItem(tr("Automatic"), PlaylistSaveOptions::Paths_Automatic);
-  ui->filePaths->addItem(tr("Relative"), PlaylistSaveOptions::Paths_Relative);
-  ui->filePaths->addItem(tr("Absolute"), PlaylistSaveOptions::Paths_Absolute);
-
-  ui->pathSeparators->addItem(tr("Automatic"),
-                              PlaylistSaveOptions::Separators_Automatic);
-  ui->pathSeparators->addItem(tr("Windows-style") + " (\\)",
-                              PlaylistSaveOptions::Separators_Windows);
-  ui->pathSeparators->addItem(tr("Unix-style") + " (/)",
-                              PlaylistSaveOptions::Separators_Unix);
-
-  QSettings s;
-  s.beginGroup(kSettingsGroup);
-  ui->filePaths->setCurrentIndex(ui->filePaths->findData(
-      s.value("file_paths", PlaylistSaveOptions::Paths_Automatic)));
-  ui->pathSeparators->setCurrentIndex(ui->pathSeparators->findData(
-      s.value("path_separators", PlaylistSaveOptions::Separators_Automatic)));
+  ui->filePaths->addItem(tr("Automatic"), Playlist::Path_Automatic);
+  ui->filePaths->addItem(tr("Relative"), Playlist::Path_Relative);
+  ui->filePaths->addItem(tr("Absolute"), Playlist::Path_Absolute);
 }
 
 PlaylistSaveOptionsDialog::~PlaylistSaveOptionsDialog() { delete ui; }
 
 void PlaylistSaveOptionsDialog::accept() {
-  QSettings s;
-  s.beginGroup(kSettingsGroup);
-  s.setValue("file_paths",
-             ui->filePaths->itemData(ui->filePaths->currentIndex()).toInt());
-  s.setValue(
-      "path_separators",
-      ui->pathSeparators->itemData(ui->pathSeparators->currentIndex()).toInt());
+  if (ui->remember_user_choice->isChecked()) {
+    QSettings s;
+    s.beginGroup(Playlist::kSettingsGroup);
+    s.setValue(Playlist::kPathType,
+               ui->filePaths->itemData(ui->filePaths->currentIndex()).toInt());
+  }
 
   QDialog::accept();
 }
 
-PlaylistSaveOptions PlaylistSaveOptionsDialog::options() const {
-  PlaylistSaveOptions o;
-  o.filePathStyle = static_cast<PlaylistSaveOptions::FilePathStyle>(
-      ui->filePaths->itemData(ui->filePaths->currentIndex()).toInt());
-  o.pathSeparatorStyle = static_cast<PlaylistSaveOptions::PathSeparatorStyle>(
-      ui->pathSeparators->itemData(ui->pathSeparators->currentIndex()).toInt());
-  return o;
+Playlist::Path PlaylistSaveOptionsDialog::path_type() const {
+  return static_cast<Playlist::Path>(ui->filePaths->itemData(ui->filePaths->currentIndex()).toInt());
 }
diff --git a/src/playlist/playlistsaveoptionsdialog.h b/src/playlist/playlistsaveoptionsdialog.h
index 4e54d64c8..6c9db8caf 100644
--- a/src/playlist/playlistsaveoptionsdialog.h
+++ b/src/playlist/playlistsaveoptionsdialog.h
@@ -1,5 +1,5 @@
 /* This file is part of Clementine.
-   Copyright 2010, David Sansome <me@davidsansome.com>
+   Copyright 2014, David Sansome <me@davidsansome.com>
 
    Clementine is free software: you can redistribute it and/or modify
    it under the terms of the GNU General Public License as published by
@@ -20,7 +20,7 @@
 
 #include <QDialog>
 
-struct PlaylistSaveOptions;
+#include "playlist.h"
 
 namespace Ui {
 class PlaylistSaveOptionsDialog;
@@ -34,7 +34,7 @@ class PlaylistSaveOptionsDialog : public QDialog {
   ~PlaylistSaveOptionsDialog();
 
   void accept();
-  PlaylistSaveOptions options() const;
+  Playlist::Path path_type() const;
 
  private:
   static const char* kSettingsGroup;
diff --git a/src/playlist/playlistsaveoptionsdialog.ui b/src/playlist/playlistsaveoptionsdialog.ui
index f95837253..c2e004b41 100644
--- a/src/playlist/playlistsaveoptionsdialog.ui
+++ b/src/playlist/playlistsaveoptionsdialog.ui
@@ -7,7 +7,7 @@
     <x>0</x>
     <y>0</y>
     <width>348</width>
-    <height>114</height>
+    <height>116</height>
    </rect>
   </property>
   <property name="windowTitle">
@@ -15,7 +15,7 @@
   </property>
   <layout class="QVBoxLayout" name="verticalLayout">
    <item>
-    <layout class="QGridLayout" name="gridLayout" columnstretch="0,1">
+    <layout class="QGridLayout" name="gridLayout" columnstretch="0,0">
      <item row="0" column="0">
       <widget class="QLabel" name="label">
        <property name="text">
@@ -23,18 +23,25 @@
        </property>
       </widget>
      </item>
-     <item row="1" column="0">
-      <widget class="QLabel" name="label_2">
-       <property name="text">
-        <string>Path separators</string>
-       </property>
-      </widget>
-     </item>
      <item row="0" column="1">
       <widget class="QComboBox" name="filePaths"/>
      </item>
-     <item row="1" column="1">
-      <widget class="QComboBox" name="pathSeparators"/>
+    </layout>
+   </item>
+   <item>
+    <layout class="QGridLayout" name="gridLayout_2">
+     <property name="topMargin">
+      <number>0</number>
+     </property>
+     <item row="0" column="0">
+      <widget class="QCheckBox" name="remember_user_choice">
+       <property name="toolTip">
+        <string>This can be changed later through the preferences</string>
+       </property>
+       <property name="text">
+        <string>Remember my choice</string>
+       </property>
+      </widget>
      </item>
     </layout>
    </item>
diff --git a/src/playlistparsers/asxiniparser.cpp b/src/playlistparsers/asxiniparser.cpp
index 343ae1310..79b5b4a4c 100644
--- a/src/playlistparsers/asxiniparser.cpp
+++ b/src/playlistparsers/asxiniparser.cpp
@@ -50,13 +50,14 @@ SongList AsxIniParser::Load(QIODevice* device, const QString& playlist_path,
 }
 
 void AsxIniParser::Save(const SongList& songs, QIODevice* device,
-                        const QDir& dir) const {
+                        const QDir& dir,
+                        Playlist::Path path_type) const {
   QTextStream s(device);
   s << "[Reference]" << endl;
 
   int n = 1;
   for (const Song& song : songs) {
-    s << "Ref" << n << "=" << URLOrRelativeFilename(song.url(), dir) << endl;
+    s << "Ref" << n << "=" << URLOrFilename(song.url(), dir, path_type) << endl;
     ++n;
   }
 }
diff --git a/src/playlistparsers/asxiniparser.h b/src/playlistparsers/asxiniparser.h
index cb15e52ef..d8736ac1e 100644
--- a/src/playlistparsers/asxiniparser.h
+++ b/src/playlistparsers/asxiniparser.h
@@ -34,7 +34,8 @@ class AsxIniParser : public ParserBase {
   SongList Load(QIODevice* device, const QString& playlist_path = "",
                 const QDir& dir = QDir()) const;
   void Save(const SongList& songs, QIODevice* device,
-            const QDir& dir = QDir()) const;
+            const QDir& dir = QDir(),
+            Playlist::Path path_type = Playlist::Path_Automatic) const;
 };
 
 #endif  // ASXINIPARSER_H
diff --git a/src/playlistparsers/asxparser.cpp b/src/playlistparsers/asxparser.cpp
index eb99e2082..4223c06df 100644
--- a/src/playlistparsers/asxparser.cpp
+++ b/src/playlistparsers/asxparser.cpp
@@ -118,7 +118,7 @@ return_song:
 }
 
 void ASXParser::Save(const SongList& songs, QIODevice* device,
-                     const QDir&) const {
+                     const QDir&, Playlist::Path path_type) const {
   QXmlStreamWriter writer(device);
   writer.setAutoFormatting(true);
   writer.setAutoFormattingIndent(2);
diff --git a/src/playlistparsers/asxparser.h b/src/playlistparsers/asxparser.h
index 681eab17a..c46a27c4a 100644
--- a/src/playlistparsers/asxparser.h
+++ b/src/playlistparsers/asxparser.h
@@ -34,7 +34,8 @@ class ASXParser : public XMLParser {
   SongList Load(QIODevice* device, const QString& playlist_path = "",
                 const QDir& dir = QDir()) const;
   void Save(const SongList& songs, QIODevice* device,
-            const QDir& dir = QDir()) const;
+            const QDir& dir = QDir(),
+            Playlist::Path path_type = Playlist::Path_Automatic) const;
 
  private:
   Song ParseTrack(QXmlStreamReader* reader, const QDir& dir) const;
diff --git a/src/playlistparsers/cueparser.cpp b/src/playlistparsers/cueparser.cpp
index da861a381..00d1401e3 100644
--- a/src/playlistparsers/cueparser.cpp
+++ b/src/playlistparsers/cueparser.cpp
@@ -352,7 +352,8 @@ qint64 CueParser::IndexToMarker(const QString& index) const {
 }
 
 void CueParser::Save(const SongList& songs, QIODevice* device,
-                     const QDir& dir) const {
+                     const QDir& dir,
+                     Playlist::Path path_type) const {
   // TODO
 }
 
diff --git a/src/playlistparsers/cueparser.h b/src/playlistparsers/cueparser.h
index 0f07b0b11..13ca9d067 100644
--- a/src/playlistparsers/cueparser.h
+++ b/src/playlistparsers/cueparser.h
@@ -54,7 +54,8 @@ class CueParser : public ParserBase {
   SongList Load(QIODevice* device, const QString& playlist_path = "",
                 const QDir& dir = QDir()) const;
   void Save(const SongList& songs, QIODevice* device,
-            const QDir& dir = QDir()) const;
+            const QDir& dir = QDir(),
+            Playlist::Path path_type = Playlist::Path_Automatic) const;
 
  private:
   // A single TRACK entry in .cue file.
diff --git a/src/playlistparsers/m3uparser.cpp b/src/playlistparsers/m3uparser.cpp
index 1b7087119..6f6874982 100644
--- a/src/playlistparsers/m3uparser.cpp
+++ b/src/playlistparsers/m3uparser.cpp
@@ -105,7 +105,8 @@ bool M3UParser::ParseMetadata(const QString& line,
 }
 
 void M3UParser::Save(const SongList& songs, QIODevice* device,
-                     const QDir& dir) const {
+                     const QDir& dir,
+                     Playlist::Path path_type) const {
   device->write("#EXTM3U\n");
 
   QSettings s;
@@ -124,7 +125,7 @@ void M3UParser::Save(const SongList& songs, QIODevice* device,
                          .arg(song.title());
       device->write(meta.toUtf8());
     }
-    device->write(URLOrRelativeFilename(song.url(), dir).toUtf8());
+    device->write(URLOrFilename(song.url(), dir, path_type).toUtf8());
     device->write("\n");
   }
 }
diff --git a/src/playlistparsers/m3uparser.h b/src/playlistparsers/m3uparser.h
index 431e5728b..c8695e5bd 100644
--- a/src/playlistparsers/m3uparser.h
+++ b/src/playlistparsers/m3uparser.h
@@ -42,7 +42,8 @@ class M3UParser : public ParserBase {
   SongList Load(QIODevice* device, const QString& playlist_path = "",
                 const QDir& dir = QDir()) const;
   void Save(const SongList& songs, QIODevice* device,
-            const QDir& dir = QDir()) const;
+            const QDir& dir = QDir(),
+            Playlist::Path path_type = Playlist::Path_Automatic) const;
 
  private:
   enum M3UType {
diff --git a/src/playlistparsers/parserbase.cpp b/src/playlistparsers/parserbase.cpp
index d095ea2d5..2a3b7dab2 100644
--- a/src/playlistparsers/parserbase.cpp
+++ b/src/playlistparsers/parserbase.cpp
@@ -86,22 +86,17 @@ Song ParserBase::LoadSong(const QString& filename_or_url, qint64 beginning,
   return song;
 }
 
-QString ParserBase::URLOrRelativeFilename(const QUrl& url,
-                                          const QDir& dir) const {
+QString ParserBase::URLOrFilename(const QUrl& url,
+                                  const QDir& dir,
+                                  Playlist::Path path_type) const {
   if (url.scheme() != "file") return url.toString();
 
-  QSettings s;
-  s.beginGroup(Playlist::kSettingsGroup);
-  int p = s.value(Playlist::kPathType, Playlist::Path_Automatic).toInt();
-  const Playlist::Path path = static_cast<Playlist::Path>(p);
-  s.endGroup();
-
   const QString filename = url.toLocalFile();
 
-  if (path != Playlist::Path_Absolute && QDir::isAbsolutePath(filename)) {
+  if (path_type != Playlist::Path_Absolute && QDir::isAbsolutePath(filename)) {
     const QString relative = dir.relativeFilePath(filename);
 
-    if (!relative.startsWith("../") || path == Playlist::Path_Relative)
+    if (!relative.startsWith("../") || path_type == Playlist::Path_Relative)
       return relative;
   }
   return filename;
diff --git a/src/playlistparsers/parserbase.h b/src/playlistparsers/parserbase.h
index 9b01dd546..d12feece4 100644
--- a/src/playlistparsers/parserbase.h
+++ b/src/playlistparsers/parserbase.h
@@ -22,6 +22,7 @@
 #include <QDir>
 
 #include "core/song.h"
+#include "playlist/playlist.h"
 
 class LibraryBackendInterface;
 
@@ -51,7 +52,8 @@ class ParserBase : public QObject {
   virtual SongList Load(QIODevice* device, const QString& playlist_path = "",
                         const QDir& dir = QDir()) const = 0;
   virtual void Save(const SongList& songs, QIODevice* device,
-                    const QDir& dir = QDir()) const = 0;
+                    const QDir& dir = QDir(),
+                    Playlist::Path path_type = Playlist::Path_Automatic) const = 0;
 
  protected:
   // Loads a song.  If filename_or_url is a URL (with a scheme other than
@@ -65,10 +67,12 @@ class ParserBase : public QObject {
   void LoadSong(const QString& filename_or_url, qint64 beginning,
                 const QDir& dir, Song* song) const;
 
-  // If the URL is a file:// URL then returns its path relative to the
-  // directory.  Otherwise returns the URL as is.
+  // If the URL is a file:// URL then returns its path, absolute or relative to
+  // the directory depending on the path_type option.
+  // Otherwise returns the URL as is.
   // This function should always be used when saving a playlist.
-  QString URLOrRelativeFilename(const QUrl& url, const QDir& dir) const;
+  QString URLOrFilename(const QUrl& url, const QDir& dir,
+                        Playlist::Path path_type) const;
 
  private:
   LibraryBackendInterface* library_;
diff --git a/src/playlistparsers/playlistparser.cpp b/src/playlistparsers/playlistparser.cpp
index 77d4573f7..9079eace8 100644
--- a/src/playlistparsers/playlistparser.cpp
+++ b/src/playlistparsers/playlistparser.cpp
@@ -131,7 +131,8 @@ SongList PlaylistParser::LoadFromDevice(QIODevice* device,
 }
 
 void PlaylistParser::Save(const SongList& songs,
-                          const QString& filename) const {
+                          const QString& filename,
+                          Playlist::Path path_type) const {
   QFileInfo info(filename);
 
   // Find a parser that supports this file extension
@@ -145,5 +146,5 @@ void PlaylistParser::Save(const SongList& songs,
   QFile file(filename);
   file.open(QIODevice::WriteOnly);
 
-  return parser->Save(songs, &file, info.absolutePath());
+  return parser->Save(songs, &file, info.absolutePath(), path_type);
 }
diff --git a/src/playlistparsers/playlistparser.h b/src/playlistparsers/playlistparser.h
index 455afb087..d25eb7e59 100644
--- a/src/playlistparsers/playlistparser.h
+++ b/src/playlistparsers/playlistparser.h
@@ -22,6 +22,7 @@
 #include <QObject>
 
 #include "core/song.h"
+#include "playlist/playlist.h"
 
 class ParserBase;
 class LibraryBackendInterface;
@@ -48,7 +49,7 @@ class PlaylistParser : public QObject {
   SongList LoadFromDevice(QIODevice* device,
                           const QString& path_hint = QString(),
                           const QDir& dir_hint = QDir()) const;
-  void Save(const SongList& songs, const QString& filename) const;
+  void Save(const SongList& songs, const QString& filename, Playlist::Path) const;
 
  private:
   QString FilterForParser(const ParserBase* parser,
diff --git a/src/playlistparsers/plsparser.cpp b/src/playlistparsers/plsparser.cpp
index f5eb2ce4c..9edce3061 100644
--- a/src/playlistparsers/plsparser.cpp
+++ b/src/playlistparsers/plsparser.cpp
@@ -62,7 +62,7 @@ SongList PLSParser::Load(QIODevice* device, const QString& playlist_path,
 }
 
 void PLSParser::Save(const SongList& songs, QIODevice* device,
-                     const QDir& dir) const {
+                     const QDir& dir, Playlist::Path path_type) const {
   QTextStream s(device);
   s << "[playlist]" << endl;
   s << "Version=2" << endl;
@@ -70,7 +70,7 @@ void PLSParser::Save(const SongList& songs, QIODevice* device,
 
   int n = 1;
   for (const Song& song : songs) {
-    s << "File" << n << "=" << URLOrRelativeFilename(song.url(), dir) << endl;
+    s << "File" << n << "=" << URLOrFilename(song.url(), dir, path_type) << endl;
     s << "Title" << n << "=" << song.title() << endl;
     s << "Length" << n << "=" << song.length_nanosec() / kNsecPerSec << endl;
     ++n;
diff --git a/src/playlistparsers/plsparser.h b/src/playlistparsers/plsparser.h
index 4fc10b6aa..3bc57a9e8 100644
--- a/src/playlistparsers/plsparser.h
+++ b/src/playlistparsers/plsparser.h
@@ -34,7 +34,8 @@ class PLSParser : public ParserBase {
   SongList Load(QIODevice* device, const QString& playlist_path = "",
                 const QDir& dir = QDir()) const;
   void Save(const SongList& songs, QIODevice* device,
-            const QDir& dir = QDir()) const;
+            const QDir& dir = QDir(),
+            Playlist::Path path_type = Playlist::Path_Automatic) const;
 };
 
 #endif  // PLSPARSER_H
diff --git a/src/playlistparsers/wplparser.cpp b/src/playlistparsers/wplparser.cpp
index d4b9ea351..0dc022f35 100644
--- a/src/playlistparsers/wplparser.cpp
+++ b/src/playlistparsers/wplparser.cpp
@@ -77,7 +77,7 @@ void WplParser::ParseSeq(const QDir& dir, QXmlStreamReader* reader,
 }
 
 void WplParser::Save(const SongList& songs, QIODevice* device,
-                     const QDir& dir) const {
+                     const QDir& dir, Playlist::Path path_type) const {
   QXmlStreamWriter writer(device);
   writer.setAutoFormatting(true);
   writer.setAutoFormattingIndent(2);
@@ -98,7 +98,7 @@ void WplParser::Save(const SongList& songs, QIODevice* device,
       StreamElement seq("seq", &writer);
       for (const Song& song : songs) {
         writer.writeStartElement("media");
-        writer.writeAttribute("src", URLOrRelativeFilename(song.url(), dir));
+        writer.writeAttribute("src", URLOrFilename(song.url(), dir, path_type));
         writer.writeEndElement();
       }
     }
diff --git a/src/playlistparsers/wplparser.h b/src/playlistparsers/wplparser.h
index 2b0bd3ec1..cf295f277 100644
--- a/src/playlistparsers/wplparser.h
+++ b/src/playlistparsers/wplparser.h
@@ -32,7 +32,8 @@ class WplParser : public XMLParser {
 
   SongList Load(QIODevice* device, const QString& playlist_path,
                 const QDir& dir) const;
-  void Save(const SongList& songs, QIODevice* device, const QDir& dir) const;
+  void Save(const SongList& songs, QIODevice* device, const QDir& dir,
+            Playlist::Path path_type = Playlist::Path_Automatic) const;
 
  private:
   void ParseSeq(const QDir& dir, QXmlStreamReader* reader,
diff --git a/src/playlistparsers/xspfparser.cpp b/src/playlistparsers/xspfparser.cpp
index 7713aacf4..7f452684c 100644
--- a/src/playlistparsers/xspfparser.cpp
+++ b/src/playlistparsers/xspfparser.cpp
@@ -103,7 +103,7 @@ return_song:
 }
 
 void XSPFParser::Save(const SongList& songs, QIODevice* device,
-                      const QDir& dir) const {
+                      const QDir& dir, Playlist::Path path_type) const {
   QFileInfo file;
   QXmlStreamWriter writer(device);
   writer.setAutoFormatting(true);
@@ -120,7 +120,7 @@ void XSPFParser::Save(const SongList& songs, QIODevice* device,
 
   StreamElement tracklist("trackList", &writer);
   for (const Song& song : songs) {
-    QString filename_or_url = URLOrRelativeFilename(song.url(), dir).toUtf8();
+    QString filename_or_url = URLOrFilename(song.url(), dir, path_type).toUtf8();
 
     StreamElement track("track", &writer);
     writer.writeTextElement("location", filename_or_url);
@@ -154,7 +154,7 @@ void XSPFParser::Save(const SongList& songs, QIODevice* device,
           // playlist.
           QUrl url = QUrl(art_filename);
           url.setScheme("file");  // Need to explicitly set this.
-          art_filename = URLOrRelativeFilename(url, dir).toUtf8();
+          art_filename = URLOrFilename(url, dir, path_type).toUtf8();
         } else {
           // Just use whatever URL was in the Song.
           art_filename = art;
diff --git a/src/playlistparsers/xspfparser.h b/src/playlistparsers/xspfparser.h
index 0102c1288..fc7d1fb70 100644
--- a/src/playlistparsers/xspfparser.h
+++ b/src/playlistparsers/xspfparser.h
@@ -39,7 +39,8 @@ class XSPFParser : public XMLParser {
   SongList Load(QIODevice* device, const QString& playlist_path = "",
                 const QDir& dir = QDir()) const;
   void Save(const SongList& songs, QIODevice* device,
-            const QDir& dir = QDir()) const;
+            const QDir& dir = QDir(),
+            Playlist::Path path_type = Playlist::Path_Automatic) const;
 
  private:
   Song ParseTrack(QXmlStreamReader* reader, const QDir& dir) const;
diff --git a/src/ui/behavioursettingspage.cpp b/src/ui/behavioursettingspage.cpp
index 48b49ac02..857d63c66 100644
--- a/src/ui/behavioursettingspage.cpp
+++ b/src/ui/behavioursettingspage.cpp
@@ -146,6 +146,8 @@ void BehaviourSettingsPage::Load() {
     case Playlist::Path_Relative:
       ui_->b_relative_path->setChecked(true);
       break;
+    case Playlist::Path_Ask_User:
+      ui_->b_ask_path->setChecked(true);
   }
   ui_->b_write_metadata->setChecked(
       s.value(Playlist::kWriteMetadata, true).toBool());
@@ -185,6 +187,8 @@ void BehaviourSettingsPage::Save() {
     path = Playlist::Path_Absolute;
   } else if (ui_->b_relative_path->isChecked()) {
     path = Playlist::Path_Relative;
+  } else if (ui_->b_ask_path->isChecked()) {
+    path = Playlist::Path_Ask_User;
   }
 
   s.beginGroup(MainWindow::kSettingsGroup);
diff --git a/src/ui/behavioursettingspage.ui b/src/ui/behavioursettingspage.ui
index a875bcfdd..ed4596058 100644
--- a/src/ui/behavioursettingspage.ui
+++ b/src/ui/behavioursettingspage.ui
@@ -265,6 +265,13 @@
         </property>
        </widget>
       </item>
+      <item>
+       <widget class="QRadioButton" name="b_ask_path">
+        <property name="text">
+         <string>Ask when saving</string>
+        </property>
+       </widget>
+      </item>
       <item>
        <spacer name="verticalSpacer_7">
         <property name="orientation">