7 times David Letterman proved himself one of TV's biggest flirts

By Shanda Deziel for Chatelaine

When David Letterman retires on May 20, TV will lose one of its favourite ladies’ men. We need look no further than a recent on-the-lips kiss with Julia Roberts to remember his propensity for flirting with female guests, charming not only Hollywood's leading ladies but also rock stars and a particular Canadian sexpert.

Read More: See the 10 most memorable Late Show with David Letterman moments

As David wraps up 33 years of hosting Late Show with David Letterman - to spend more time with the most important woman in his life, wife Regina, and their 11-year-old son, Harry - Chatelaine look back on his most memorable flirtations, flashes and make-out sessions.

1. LATE-NIGHT SEX SHOW

Photo: © Getty Images

Canada’s favourite sex educator, Sue Johanson, had a fantastic rapport with Dave, both charming and flustering him with questions about his sex life and waving sex toys around with abandon. One of the show's favourite guests, she was on six times in five years, and would have made even more appearances if she wasn't too busy talking sex at Canadian high schools and universities to make the trip to New York.

2. 'YOU'RE REALLY A HANDSOME WOMAN'

David Letterman sends Julia Roberts a bouquet of flowers every year on her birthday, and when she visits the show he always regales her with sincere compliments. Think: "You're a lovely woman. You're an attractive woman. You're really a handsome woman." The surprising thing is the crush seems to be mutual — and Julia swears she's asked Dave out — and been rejected — twice.

3. HAPPY BIRTHDAY, MR LETTERMAN

Dave may not approve of Drew Barrymore's tattoos and tongue piercing, but he can't resist her flirtations. And the time she flashed him, on his birthday in 1995, is high up on his Top 10 list of career highlights.

4. TICKLE FIGHT

It took Cher four years to agree to come on Dave’s show, and the first interview started off like a bad blind date. Dave opened with "You smell terrific," and a defensive Cher responded, "Is this as good as it gets?" Turns out, they had fantastic chemistry. In one appearance, their banter even led to an uncharacteristic (for both of them) tickle fight.

5. ENDLESS KISS

In her first-ever appearance, Dave was fascinated by Gillian Anderson's stories of wild teenage years and much-older boyfriends. Years later, they engaged in late night's longest make-out session. But he didn't keep his promise to have her on the show more times than her X-Files costar, David Duchovny, who appeared 13 times. (Dave has man crushes too.)

6. CUTE AND CUDDLY

Over the years, Dave and Jennifer Lawrence’s relationship went from fist bumps to snuggling together under a blanket. While Dave does seem concerned with her manic energy, he has a habit of falling for America's sweethearts (see: Julia Roberts).

7. HE'S WITH THE BAND

Dave pretty much jumpstarted the Canadian singer's career after he had her on twice in a three-week period for her debut album, Failer. For her third appearance, Edwards took an overnight Greyhound from Ottawa to New York when her flight was cancelled. Later Dave offered to get on a bus for her, hinting at his retirement plans: "From time to time we'll have musical acts on the show and I will travel with the band,” he told Edwards. “I would like to travel with you. So send me an itinerary."

This story was originally published on Chatelaine.com

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