The dating pool of Hollywood is so small, it almost feels that everyone has dated each other. With their lives always in the spotlight, fans usually know what their favorite stars are up to at all times. From traveling to the gym to taking out their trash cans, or showing up at the airport for a flight, they are being watched almost every time. Hence, it’s almost miraculous that some celebrities can hide their relationships and secretly date — or secretly marry and secretly have kids — without anyone noticing and spilling the details to the tabloids.
Check out this list of celebrities who dated so secretly that the news flew under the radar.
1. Angelina Jolie and Billy Bob Thornton
Time together: Angelina and Billy Bob were married from 2000 to 2003.
2. Tom Cruise and Cher
Time together: Cher and Tom dated briefly in 1985.
3. Kaley Cuoco and Henry Cavill
Time together: Kaley and Henry dated briefly— like a few weeks — back in 2013.
4. Whoopi Goldberg and Ted Danson
Time together: Whoopi and Ted were together from 1992 to 1994.
5. Matthew Broderick and Jennifer Grey
Time together: Jennifer and Matthew dated from 1987 to 1988.
6. Ryan Reynolds and Alanis Morissette
Time together: Alanis and Ryan started dating in 2002 and were engaged from 2004 to 2007.
7. Lizzy Caplan and Matthew Perry
Time together: Lizzy and Matthew secretly dated from 2006 to 2012.
8. Courteney Cox and Michael Keaton
Time together: Courteney and Michael were together from 1989 to 1995.
9. Blake Lively and Ryan Gosling
Time together: Blake and Ryan had a brief fling back in October 2010.
10. Kiefer Sutherland and Julia Roberts
Time together: Julia and Kiefer dated and were engaged between 1990 and 1991.
11. Jason Segel and Michelle Williams
Time together: Michelle and Jason were together from 2012 to 2013.
12. Tom Hiddleston and Taylor Swift
Time together: Taylor and Tom were together during the summer of 2016.
13. Sarah Jessica Parker and Robert Downey Jr.
Time together: Sarah and Robert were together from 1984 to 1991.
14. Chris Pine and Zoë Kravitz
Time together: Zoë and Chris have been linked together a couple of times — once in 2010, and then again in 2013.
15. Anne Hathaway and Topher Grace
Time together: Anne and Topher dated from 1999 to 2001.
16. Matthew Morrison and Lea Michele
Time together: Lea and Matthew briefly dated back in 2010.
17. Justin Timberlake and Cameron Diaz
Time together: Cameron and Justin dated from 2003 to 2006.
18. Evan Rachel Wood and Marilyn Manson
Time together: Evan and Marilyn began dating in 2007 and were engaged in 2010.
19. Madonna and Tupac
Time together: Madonna and Tupac briefly dated in 1993.
20. Penélope Cruz and Orlando Bloom
Time together: Penélope and Orlando were briefly linked back in 2006.
21. Drew Barrymore and Justin Long
Time together: Drew and Justin dated on and off from 2007 to 2010.
22. Keira Knightley and Jamie Dornan
Time together: Keira and Jamie dated from 2003 to 2005.
23. Ashton Kutcher and Brittany Murphy
Time together: Brittany and Ashton dated in 2005.
24. Wilmer Valderrama and Mandy Moore
Time together: Mandy and Wilmer dated from 2000 to 2002.
25. Britney Spears and Colin Farrell
Time together: Britney and Colin were briefly linked back in 2003.
26. Samantha Ronson and Lindsay Lohan
Time together: Lindsay and Samantha dated in 2009.
27. Rihanna and Shia LaBeouf
Time together: Rihanna and Shia went on a single date in 2007.
28. Ashley Olsen and Lance Armstrong
Time together: Ashley and Lance dated in 2007.
29. Nick Cannon and Kim Kardashian West
Time together: Kim and Nick dated for a few months between 2006 and 2007.
30. Aubrey Plaza and Michael Cera
Time together: Aubrey and Michael dated for a year and a half after the release of Scott Pilgrim vs. the World.
31. Last but not least, Jaden Smith and Kylie Jenner
Time together: Kylie and Jaden dated in 2013.
Which secret celebrity pairing shocked you the most? Tell us in the comment section below: