Jon Hamm is getting candid about a milestone moment in his life.
The 45-year-old actor recently opened up about losing his virginity while promoting his new film, Keeping Up With the Joneses, and admitted it was an "awkward" experience. Hamm jokes that he would change "everything" about it.
"There's no version of it that's not awkward," he tells Elle magazine. "Let's put it this way: As much as I had practiced, I was still not quite ready for game time."
Hamm says he lost his virginity when he was 19 years old, and in college.
"I don't know why that would surprise you," he says when the interviewer assumes he would have lost it at a younger age. "Maybe it's easy for some people. It certainly wasn't for me."
See photos of Jon Hamm:
Jon Hamm through the years
Jon Hamm through the years
LOS ANGELES, CA - JANUARY 10: Jon Hamm attends the HBO's Post 2016 Golden Globe Awards Party held at Circa 55 Restaurant on January 10, 2016 in Los Angeles, California. (Photo by Tommaso Boddi/WireImage)
Actor Jon Hamm poses in press room at the 67th Annual Peabody Awards at the Waldorf-Astoria on Monday, June 16, 2008 in New York. (AP Photo/Evan Agostini)
Actor Jon Hamm, from the AMC show "Mad Men", smiles during the Television Critics Association summer press tour in Beverly Hills, Calif. on Wednesday, July 9, 2008. (AP Photo/ Matt Sayles)
Actor Jon Hamm arrives at the 2008 Primetime Emmy Awards Nominees for Outstanding Performance reception in Los Angeles on Friday, Sept. 19, 2008. (AP Photo/Matt Sayles)
Actor Jon Hamm and Jennifer Westfeldt attend the premiere of "The Day The Earth Stood Still" in New York on Tuesday, Dec. 9, 2008. (AP Photo/Peter Kramer)
Jon Hamm, a cast member in the AMC series "Mad Men," arrives at the Season 3 premiere of the show in Los Angeles, Monday, Aug. 3, 2009. (AP Photo/Chris Pizzello)
Jon Hamm, left, and Jennifer Westfeldt arrive at the 67th Annual Golden Globe Awards on Sunday, Jan. 17, 2010, in Beverly Hills, Calif. (AP Photo/Matt Sayles)
Actor Jon Hamm presents the award for Guy Movie Of The Year onstage at Spike TV "Guy's Choice" awards in Culver City, Calif., on Saturday, June 5, 2010. (AP Photo/Chris Pizzello)
Jon Hamm arrives at the 62nd Primetime Emmy Awards Sunday, Aug. 29, 2010, in Los Angeles. (AP Photo/Matt Sayles)
Actor Jon Hamm at the TIFF press conference for the feature film "The Town" in Toronto on Friday, Sept. 10, 2010. (AP Photo/Dan Steinberg)
Actor Jon Hamm attends The National Board of Review of Motion Pictures at Cipriani's 42nd Street on Tuesday, Jan. 11, 2011 in New York. (AP Photo/Evan Agostini)
Jon Hamm, right, and January Jones, cast members in the television series "Mad Men," pose together before the PaleyFest 2012 panel discussion on the show, Tuesday, March 13, 2012, in Beverly Hills, Calif. The new season of "Mad Men" begins on Sunday, March 25. (AP Photo/Chris Pizzello)
Actor Jon Hamm attends a special screening of "The Campaign" at the Sunshine Landmark Theatre on Wednesday July 25, 2012 in New York. (Photo by Evan Agostini/Invision/AP)
Jon Hamm, left, and Jennifer Westfeldt arrive at the 64th Primetime Emmy Awards at the Nokia Theatre on Sunday, Sept. 23, 2012, in Los Angeles. (Photo by Matt Sayles/Invision/AP)
Host Jon Hamm speaks at the ESPY Awards on Wednesday, July 17, 2013, at Nokia Theater in Los Angeles. (Photo by John Shearer/Invision/AP)
Jon Hamm, left, and Jennifer Westfeldt arrive at the 65th Primetime Emmy Awards at Nokia Theatre on Sunday Sept. 22, 2013, in Los Angeles. (Photo by Jordan Strauss/Invision/AP)
Jon Hamm, star of the upcoming film "Million Dollar Arm," waves to the audience as he arrives onstage at the Walt Disney Studios presentation on the third day of CinemaCon 2014 on Wednesday, March 26, 2014 in Las Vegas. (Photo by Chris Pizzello/Invision/AP)
Jon Hamm arrives at the world premiere of "Million Dollar Arm" at El Capitan Theatre on Tuesday, May 6, 2014, in Los Angeles. (Photo by Chris Pizzello/Invision/AP)
Jon Hamm, right, poses with his wax likeness at its unveiling at Madame Tussauds on Friday, May 9, 2014 in New York. (Photo by Charles Sykes/Invision/AP)
Jon Hamm, left, and Jennifer Westfeldt arrives at the 66th Annual Primetime Emmy Awards at the Nokia Theatre L.A. Live on Monday, Aug. 25, 2014, in Los Angeles. (Photo by Richard Shotwell/Invision/AP)
Jon Hamm arrives at the 4th Annual Stand Up 2 Cancer Live Benefit at The Dolby Theatre on Friday, Sept. 5, 2014, in Los Angeles. (Photo by Jordan Strauss/Invision/AP)
Jon Hamm speaks on stage during the "Mad Men" panel at the AMC 2015 Winter TCA on Friday, Jan. 10, 2015, in Pasadena, Calif. (Photo by Richard Shotwell/Invision/AP)
Jon Hamm appears at an unveiling of a bench dedicated to the "Mad Men" series in front of the Time & Life Building on Monday, March 23, 2015 in New York. The bench shows a silhouette of Hamm's character Don Draper. (Photo by Charles Sykes/Invision/AP)
Jon Hamm arrives at The Black And Red Ball In Celebration Of The Final Seven Episodes Of "Mad Men" on Wednesday, March 25, 2015, in Los Angeles. (Photo by Richard Shotwell/Invision/AP)
Jon Hamm arrives at the Los Angeles premiere of "Minions" at the Shrine Auditorium on Saturday, June 27, 2015. (Photo by Richard Shotwell/Invision/AP)
Jon Hamm with the award for outstanding lead actor in a drama series for âMad Menâ poses in the press room at the 67th Primetime Emmy Awards on Sunday, Sept. 20, 2015, at the Microsoft Theater in Los Angeles. (Photo by Jordan Strauss/Invision/AP)
Jon Hamm poses in the press room with the award for best performance by an actor in a TV series - drama for âMad Menâ at the 73rd annual Golden Globe Awards on Sunday, Jan. 10, 2016, at the Beverly Hilton Hotel in Beverly Hills, Calif. (Photo by Jordan Strauss/Invision/AP)
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But he has this advice for his 20-year-old self.
"The best thing you could say is: Appreciate it," he shares. "Struggle is part of the journey. That's what I've learned in my forties: This too shall pass."
Although Hamm has clearly aged well, even he admits to being insecure about getting older.
"Getting old sucks," he says bluntly. "I had an interesting conversation with an older actor whom I've looked up to for many years. He said, 'When I wake up in the morning, I still think I'm 35. It's not until I see myself in the mirror where I'm like, 'Oh, right'...' I have that, too. That horrible realization that you're not what you used to be."
Of course, there's also an upside.
"Listen, I'll say this, too. The great thing about getting older is living life," he adds.
"I don't know. I think life's too short, you know?" the 27-year-old singer told ET exclusively when asked why he decided to open up. "I mean, ultimately, I think of myself as an honest guy. There are just those moments in life where you have to be true to yourself and true to the world."