When it comes to talking to our kids about the “hard stuff” like sex, drugs, bullying, porn, racism, or the many other issues facing our society today, many parents find themselves shying away from difficult conversations. They worry that by bringing up these issues they will be introducing their children to inappropriate topics, or bringing up something their child has never heard of or thought about. While it is possible that taking a fairly pro-active approach to discussing difficult things with your kids might bring up new topics, this allows you to control the conversation and present things in keeping with your own value system. It prevents having to do after-the-fact damage control following little Jimmy’s playground conversation with an older kid about where babies come from. And it gives your kid the message that you are someone they can come to when they need to talk about hard things.
So how do you start a conversation with your child about a topic that may make you uncomfortable? Here are 7 things to consider when approaching a difficult conversation with your kids.
Clarify your own values.
If it is time to have a talk with your kids about drugs, and you’ve got mixed feelings about your own past marijuana use, this is the time to sort out in your mind what you believe would be in your kids’ best interest. Or if your own parents were militant that sex should only occur within marriage, but you didn’t do that yourself, figure out what message you want to send to your children about it. There isn’t a right or wrong answer here—everyone has a somewhat different value system. Most of us would agree to the basic ideas that we should treat ourselves and others with respect and kindness, which is always a good place to start. But know what message you want to convey before you start talking about it
Be age appropriate.
A six-year-old and a fourteen-year-old can have very different sorts of conversations. A younger child needs help developing empathy and understanding of why we hold certain values, while an older child or teen can think more about social justice and their own personal values that may be separate from the family. Don’t try to give kids more than they are ready for, and don’t try to dumb down your conversations with older kids
Time your conversations wisely.
Some people like to sit down and “have a talk,” but for others these conversations are better had in the car on the way to soccer practice. Some kids have a hard time tolerating a conversation where they feel like they are in the hot seat, so approaching things more casually can make them more comfortable. Also, remember that the idea that you have “the sex talk” or “the drugs talk” with your kids and are done is a fallacy. You need to have many talks, some shorter, some longer, until both you and your kid can relax into the idea that this is just something you talk to each other about.
Be topical.
Use various forms of media as a way to enter into a conversation with your kid about difficult topics. Maybe you just watched an episode of your favorite television show that touched on racism, or there is a front-page article in the paper about sexual harassment. Use these things as a way to enter a conversation with your kid, as well as a way to invite them to share their thoughts. Another idea is to use communication coming from your child’s school as an entry point—when the Netflix show “13 Reasons Why” came out, many schools sent emails to parents cautioning them that this show about the suicide of a teenage girl could have an impact on students experiencing depression and anxiety themselves. “I got an email from your school about____” is the perfect way to bring up something potentially hard to talk about. Then the school is the bad guy forcing you both to have this uncomfortable conversation!
Be curious. 
Talking about difficult topics shouldn’t be an opportunity for you to drone on, lecture-style with your kid. You need to reign yourself in a bit if you find yourself bloviating. The idea is to communicate your values to your child while inviting them to communicate theirs to you. If they express something surprising or at odds with your beliefs, try to ask questions rather than get angry. Kids are much more likely to listen if they feel listened to.
Be prepared for anything. 
Bringing up a difficult topic could be met with eye rolls or with interest. Even if your kid looks at you like a deer in the headlights, keep going. You are creating a culture in which your child understands that difficult things can be spoken of, and that if they have questions they can come to you.
Be genuine. 
Kids know when we are uncomfortable. If the idea of talking to your teenager about condoms makes you want to crawl out of your skin, own it. Say, “I feel totally uncomfortable bringing this up, but I think it’s really important that we talk about it.” You don’t need to be an expert to have hard conversations.
Don’t let fear or discomfort stop you from having hard conversations with your kids. You are the person they need to hear from, as well as the person they need to feel they can talk to. Remember, you and your kid are in this together.