Did you ever ask your mom or dad if they had sex before marriage or if they tried any drugs in their younger years, and they responded with sheepish claims that they never did any of that, and furthermore, didn't even think of it? Yeah, I'm with you. My parents were like that. But because I never believed my mom about being a virtual angel until her 20s, and I really hated the fact that she tried to make it seem like she was, I decided to be totally honest with my kid about my past. Granted, my child is still a toddler and thankfully not plying me with questions about my virginity and experiences with marijuana, but when the time does come, I am definitely in the camp of total open honesty. Even if it embarrasses him, 'cuz well, isn't that what parents are for sometimes?
That said, I don't know if it's the best idea to be totally and completely candid with your kids. I mean, I will definitely not be telling my son someday about the kinds of things I did with boys before my freshman year of high school was even over, but I also won't shy away from any of his questions about my past, if only to help him relate his own issues and feel not so awkward and alone. Even though the awkwardness of adolescence isn't exactly totally avoidable, I think that there is a not-insignificant amount of comfort to be taken from knowing that your parents — the closest adults to you as you're going through the awkwardness of growing up — went through some sh*t too, and still managed to turn into the solid, stable(-ish) adults they are. There's power in that.
Not only does being honest with your kid make for a better relationship with them overall, but it also feels kind of great to be honest and open with them. It's really not too difficult to see the ways that being honest with your kid about your past is good for you both. Being real with your kid isn't just for their benefit — it's definitely a win-win situation. Here's how: