Restore DB from SQL Server 2008 R2 to 2014 Express
Yes, you can, as long as the database is &lt; 10 GB and doesn't use any features not supported by Express (you didn't mention what edition was being used in 2008 R2). 

Stop using the broken point-and-click UI, and instead use a proper RESTORE DATABASE command:

RESTORE DATABASE DBFrom2008 FROM DISK = 'C:\backups\2008backup.bak'
  WITH REPLACE, RECOVERY,
  MOVE 'data_file_name' TO 'C:\...\database_name.mdf',
  MOVE 'log_file_name'  TO 'C:\...\database_name.ldf';


If you get errors from that (after replacing all of the obvious bits that are specific to your database and system), post those.