MOMS, DAUGHTERS, ANGER, LOVE, DEATH & BACK RUBS

A couple recent conversations have really made me evaluate my role as mother. A friend from my mom's group is moving and I went over to help with her 3-month-old daughter while she did some packing. My Girl and her son were both at preschool, so it was nice to be able to talk candidly (and smell the fresh-baked baby's head). As we were talking about parenting strategies/philosophies the topic of our mothers came up. My friend is also a member of the dead mother club and I told her about the Motherless Mothers book. She was interested and we started talking about not making the same mistakes as our mothers with our girls.
Turns out we were both disrespectful, angry young adults who partied and were very fortunate to escape with nothing more than a long list of men and drugs sampled. How will we ensure our daughters talk to us? How can we let them know that we made stupid choices, yet not have them think we are hypocritical. "Sure I tried *insert drug of choice here* but it was dumb. I'm lucky I was never arrested or hurt. You shouldn't try it." WTF are we going to say?
We talked for 20 minutes on the topic before finally agreeing that this is the basis of our actions: "When I was younger, I felt something was missing in my life. I tried to fill that void with people who didn't really care about my happiness. I did things that were dangerous and embarrassing. I was not living a healthy life."
So how do we make sure nothing is missing in their lives? We could only come up with talking. Opening up emotionally to our daughters. Teaching them to open up. Giving them a way to talk to us instead of "acting out." But how exactly (throwing our arms up in exasperation) do we do that?
We both practice infant/toddler massage and have heard that as kids get older it is a great way to get them to open up. Kids talk more freely and are relaxed when they are getting a back rub. There are no TVs or computers to distract them. They also can't see your face, your reactions, your judging. And that's when you throw in something along the lines of, "So how did your speech go in history class?" or "What kind of things did so-and-so get for her birthday?"
Could work. Then again, our daughters could just roll their eyes and count the hours until they move into the dorm. Shit, this stuff is hard. I'm just glad to know I'm not the only motherless mother of a daughter who is scared shitless about the past repeating itself. Thank goodness my friend will only be an email away.