Jeffrey R. Staab/CBS/Getty
May 13, 2015 07:05 AM

Julia Roberts and Late Show host David Letterman have had one of the best flirtations on TV for decades. On Wednesday, May 20, Letterman will retire after 30 years on late-night television – and Roberts, 47, is on the star-studded lineup. To celebrate his career, let’s take a look back at some of their best moments together.


Roberts first interviewed with Letterman, now 68, in 1989 when Late Night with David Letterman was on NBC. The star was only 22 when she came to promote Steel Magnolias. Her first time might have been one her most challenging on the show, as she had to share the spotlight with Charlie the Dog.


Roberts revealed that she had asked Letterman’s producer if the host could be her date to the premiere of Steel Magnolias. Much to Letterman’s dismay, it turned out his producer had denied Roberts’ invitation.


We found out that Letterman rejected Roberts not just once, but twice. This time, Letterman blamed the impersonal invitation Roberts’ assistant sent for his failure to accept.


Roberts has often been candid about her relationships on the Late Show. She told Letterman about her relationship with then-boyfriend Matthew Perry. When Roberts admitted she was nervous for her first date with Perry, Letterman boosted her confidence by reminding her she’s “no chimp.”


It looked like Roberts almost gave Letterman a heart attack when she flirtatiously lifted up her skirt for his hand. But Letterman insisted “this visit here is adding 10 years to my life.”


Roberts visited the show after her Oscar win for Erin Brockovich. Despite her newfound prestige, Letterman jokingly chastised her for her low-cut shirt. “Holy cow I can see right into that. Look out! It’s all right there,” he told Roberts after she leaned a little too far forward.


Roberts and Letterman shared a laugh over the host’s recent induction into fatherhood – and pondered the state of their relationship. “We’re like old marrieds” Roberts quipped. “I fell in love with you and that movie at the same time,”Letterman said of Roberts’ first time on his show.


Having had years of experience on the show, Roberts argued that Letterman was once much “tougher” on his guests. “When I was first brave enough to come on the show that was back in the day when you weren’t sweet,” Roberts said. “You were tough, and I was brave enough to come on. Now all the girls are ‘lovely’ or ‘pretty’ or ‘fantastic.’ ” Letterman assured the actress his only true affection was for her. “But you know I’m just woofing when I say that to the other girls,” he said.


During one of their giddier interviews, Letterman explained why it is so hard for him to stay on track when talking to the star. “I have such tremendous feelings for you, and I have for many many years. But I have always known better than to do anything about it because look at me,” Letterman joked. “When you got married and had the three kids it was a bittersweet moment for me because I felt nothing but happiness and joy for you, and then I also felt I don’t really have to pretend I have a shot anymore.”


On the Late Show to promote Eat Pray Love, Roberts teased Letterman about her years-long dedication to the show. “My love, my dear, we all know of my longtime affection and devotion to David Letterman,” the actress told her friend.


Letterman had some apologizing to do to his longtime guest. For the first time in 15 years, he had failed to send flowers on her birthday. But Letterman made up for it on his show by literally burying Roberts in bouquets.

The final Late Show with David Letterman airs Wednesday at 11:35 p.m. (ET) on CBS.

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