Actress Mary Tyler Moore died Wednesday at 80. And while she was known for her work on The Mary Tyler Moore Show and The Dick Van Dyke Show, one 2000 made-for-TV movie had her working with an It's Always Sunny in Philadelphia star who found it particularly difficult to hit on the Hollywood legend.

It's Always Sunny's Charlie Day appeared alongside Moore in Mary and Rhoda, a 2000 ABC made-for-TV flick that had the actress reprising her role as The Mary Tyler Moore Show's Mary Richards. Valerie Harper also reprised her role as Rhoda Morgenstern.

The flick was Day's first television job, which he recalled back in 2015 for Vanity Fair. At one point in the film, the script called for Day to hit on Moore by telling her she was "looking fine," a direction with which Day appeared somewhat uncomfortable.

"I remember how lovely Mary Tyler Moore was to me, and I thought that was really nice, considering I was only there to say one line," Day told Vanity Fair. "The line was, 'Looking fine,' and the director, Barnet Kellman, was like, 'Really tell her that she's looking good.' So I kind of had to, like, hit on Mary Tyler Moore, who is significantly older than I was at the time."

However odd it seemed, Day successfully pulled off the flirtation. The actor went on to appear in episodes of Law & Order, Luis, and Reno 911! before joining the It's Always Sunny cast in 2005. Following the film, Moore appeared on shows including The Ellen Show, That 70s Show, and Hot in Cleveland.