Donald Trump's 1999 Pick-Up Lines, Revealed!

S3 2:08
Brooke Shields revealed the details of her conversation with Donald Trump which he asked her out immediately after his 1999 divorce. Stephen reveals the pick-up lines he used on the other '90s female celebrities. Air Date: Oct 6, 2017
Weeknights at 11:35/10:35c

Full Episodes

The Late Show with Stephen Colbert - 2/15/19 (Jeff Goldblum, Jacques Torres, The Marcus King Band)
S4 E101 Feb 15, 2019
2/15/19 (Jeff Goldblum, Jacques Torres, The Marcus King Band)
The Late Show with Stephen Colbert - 2/14/19 (Bradley Cooper, Mayor Pete Buttigieg)
S4 E100 Feb 14, 2019
2/14/19 (Bradley Cooper, Mayor Pete Buttigieg)
The Late Show with Stephen Colbert - 2/13/19 (Trevor Noah, Natasha Lyonne)
S4 E99 Feb 13, 2019
2/13/19 (Trevor Noah, Natasha Lyonne)
The Late Show with Stephen Colbert - 2/12/19 (Regina King, Bill & Melinda Gates, Jena Friedman)
S4 E98 Feb 12, 2019
2/12/19 (Regina King, Bill & Melinda Gates, Jena Friedman)
The Late Show with Stephen Colbert - 2/11/19 (John Oliver, BLACKPINK)
S4 E97 Feb 11, 2019
2/11/19 (John Oliver, BLACKPINK)
S4 E96 Feb 08, 2019
2/8/19 (Glenn Close, Byron Bowers)
S4 E95 Feb 07, 2019
2/7/19 (Chris Pratt, Meghan McCain, Beirut)
S4 E94 Feb 06, 2019
2/6/19 (Steve Buscemi, Bret Baier, Sasha Sloan)
S4 E93 Feb 05, 2019
2/5/19 (Norah O'Donnell, John Dickerson, Gayle King, Bianna Golodryga, Spike Lee)
S4 E92 Feb 04, 2019
2/4/19 (Taraji P. Henson, Matt Walsh, Marie Kondo)
The Late Show with Stephen Colbert - 2/3/19 (Conan O'Brien, Steve Carell, James Taylor)
S4 E91 Feb 03, 2019
2/3/19 (Conan O'Brien, Steve Carell, James Taylor)
S4 E90 Jan 31, 2019
1/31/18 (Ellen Page, Radhika Jones, Django Gold)
Show More