Oct. 22, 2012— -- intro: Losing your virginity is an awkward subject, but one that many stars aren't afraid to talk about.
Krysten Ritter, the star of ABC's "Don't Trust the B---- in Apartment 23," held nothing back when talking to Playboy about her first experience being intimate with her high school boyfriend.
"He was so angsty and bad. ... His name was Damian, but my parents called him 'Demon,'" Ritter, now 30, told Playboy, according to the Huffington Post. "Our first time was in his parents' van before basketball practice. I don't remember it being very pleasant."
Click through to see the good, bad and downright ugly stories of celebs' first times:
quicklist: 1title: Will Ferrelltext: When funnyman Will Ferrell famously dropped his pants for a scene in "Old School," the 44-year-old actor didn't really mind.
"This kind of thing is not a big deal to me," Ferrell told Rolling Stone in March. "In college, they had this thing where you'd run naked on fraternity row, and if anyone challenged me, I'd be happy to do it."
When Ferrell lost his virginity during his junior year of college at the University of Southern California, in his mind, it wasn't a very big deal either.
"In my mind's eye, it seemed like the way it was supposed to happen," he said.
Although Ferrell waited until he was 21 to lose his v-card, his mother thought it had happened much sooner. He jokingly recalled her advice: "'I'm telling you now, if you slept with this girl, you'd better slap a condom on that pecker of yours.'"
quicklist: 2title: Matthew Morrisontext: Before Matthew Morrison was taking over the small screen on "Glee," he was ruling Broadway. When he was 19, Morrison landed his first Broadway role, in "Footloose," and he got lots of attention from the ladies.
"There were all these beautiful, beautiful dancers. As a straight guy I had some room," Morrison told Details magazine in 2010. "I definitely hooked up with a lot of girls when I was a young guy on Broadway. It was exciting. Very joyous and free."
But while Morrison, 33, was playing the field on Broadway, he kept his virginity a secret. During college, the "Glee" star joined a Bible study group and lost his virginity when he was 21.
Morrison also talked about dating the homecoming queen in high school. She once suggested they pray when things got too hot and heavy.
"It was sweet," Morrison said. "It was innocent."
quicklist: 3title: Matthew Foxtext: Matthew Fox lost his virginity when he was 12-years-old to a girl two years his senior, but the 46-year-old star said he remembers it like it was yesterday.
"I can actually see the event in my mind's eye, like photographs. It was in Dubois, Wyo., where the population sign probably says, to this day, about 1,000," Fox told Playboy in 2010, according to the Huffington Post. "It happened, literally, on the ground by a river while a rodeo was going on in town. It was absolutely terrible and awkward."
quicklist: 4title: Celine Diontext: Celine Dion lost her virginity to her manger-turned-husband Rene Angelil, who is 26 years older than the singer.
"It was in Dublin, on that unforgettable day of April 30, 1988, the evening of the Eurovision competition," Dion wrote in her book "My Story, My Dream." "He went back to my room with me. ... I was seated at the head of the bed, legs folded under the covers. I was happy about being alone with the man I loved. And I had a very precise plan."
She described more intimate details before telling readers she promised Angelil, "You'll be the first. And the only."
The couple married six years later and have been together ever since.
quicklist: 5title: Kathie Lee Giffordtext: Kathie Lee Gifford waited until she was married to have sex, but she wrote in her 1993 book, "I Can't Believe I Said That," that it wasn't exactly spectacular.
"I'm sorry, but anyone who's instantly relaxed with being naked in front of somebody for the first time and having someone explore intimate parts of the body is either lying about being relaxed -- or lying about it being the first time," Gifford wrote.
At age 22, Gifford lost her virginity to her first husband, 29-year-old Paul Johnson, who was the leader of her Bible study group.
"But [I had] some raging hormones going. I mean I was ready!" Gifford wrote. "My lifelong self-consciousness about my body seemed, miraculously, to fade right away. ... Let me tell you, I really did look divine. Relaxed? Forget it! It was, like, yabba dabba doo! I lost every inhibition I'd ever had. It was time for candles and romance, time to boogie and swing from the chandeliers.
"Yet we just couldn't seem to get relaxed with each other," she wrote. "It saddens me to think about it now. We were so uncomfortable with each other, and I felt responsible and disappointed for both of us. I spent the first night of my married life sobbing my eyes out, feeling we had just made the biggest mistake of our lives."
quicklist: 6title: Brooke Shieldstext: Brooke Shields lost her virginity when she was 22, but the model said she regrets not doing it sooner. She said if she had learned to love the way she looked earlier in life, she would have had sex earlier than 22.
"I had the public and all this pressure, and I wish I had just gotten it over with in the beginning when it was sort of OK," Shields, now 47, told Health magazine. "I think I would have been much more in touch with myself. I think I wouldn't have had issues with weight. I carried this protective 20 pounds [in college]. It was all connected."