Jon Hamm wasn't "quite ready" when he lost his virginity.
Jon Hamm
The 45-year-old actor had sex for the first time when he was 19, but admits it wasn't smooth sailing, and brands the special night as "awkward".
He said: "There's no version of it that's not awkward. Let's put it this way: As much as I had practiced, I was still not quite ready for game time."
And growing up wasn't easy for the 'Mad Men' star - who is thought to be dating ex Jennifer Westfeldt again - in other areas either, as he recalls feeling a "deep tragedy" when his mother died of cancer when he was 10.
He added: "[My father] was twice widowed. He was divorced from my mum when she died, but even so, there's a deep sense of tragedy in that. I never had the opportunity to, as an adult, sit down and talk to him about that. It's a real loss. I was quasi-adopted by my friends' families."
A further 10 years after his mother passed, the 'Million Dollar Arm' actor also lost his father, and sought counselling to help him deal with the loss.
He said previously: "After I'd lost my dad, I had this horrible paralysing inertia - and no one in my family was capable of dealing with it. So what do you do? Go and see a professional. I preach it from the mountaintops.
"I know it's a luxury and it's not something everyone can afford. But if you can, do it. It's like a mental gym."
The 'Keeping Up with the Joneses' actor says he's doing OK now though, as he feels "incredibly lucky" to have other parental figures in his life.
He told Elle magazine: "And even today I get e-mails or cards from these women who, for lack of a better word, were my mum. We talk about what it means to be a family. Mostly it's about showing up. And being aware enough to check in and say, 'How are you doing?' I've been incredibly lucky to have these people in my life."
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