Look for a natural opening
Everyday conversations with your kid can easily turn into conversations about their emotional wellbeing. Sometimes, you don't even have to bring up emotional wellbeing directly. For example, if your kid shares something that’s happening with a friend or classmate, you can ask them how that makes them feel, or whether they’ve experienced something similar. Kids may also ask caregivers about their own history of feeling upset or confused. If that happens, don’t change the subject — be open and honest about your own experiences in relevant situations and invite them to respond with theirs.
Keep it casual
Asking a kid how they're feeling doesn't have to happen at a particular time or place, and it shouldn't feel like a "big deal." In fact, it's often best if you can check in when you're already spending time together, or doing an activity your kid enjoys. You can talk when you're in transit, even if it's just for a few minutes, or while you're making dinner. Make it casual and relaxed — try not to set expectations that the conversation needs to be long or intense, and ask open-ended questions to keep the conversation flowing, as opposed to receiving just yes or no answers.
When it comes to initiating conversations about feelings, easing into it is always the way to go. One great way to initiate a broader conversation about feelings is to have them nominate something they experienced during their day that they thought was beautiful and one thing they felt had sharp edges and why they felt that way--the roses and thorns model.
Make it a habit
Talking with your kid regularly will not only strengthen your relationship with them, but it will also make it it much easier to help them navigate challenges when they arise. Make it a habit to talk to your kid about a range of emotions, and remember, nobody knows your child the way that you do, so you will know when it feels natural and comfortable to initiate these conversations. Trust your gut.
Try something different
If your child is struggling to have a conversation, there are a few other methods you can use to encourage them to share how they're feeling. You can ask them to write down their feelings. Tell them they can create a song, a poem, or just write. If there's a TV show, movie, or book that they like, you might ask them to talk about what the characters are experiencing, and whether they've experienced something similar.
Share your experiences
Sharing your own thoughts and feelings with your kid is just as important as listening to theirs. These conversations are an opportunity to demonstrate ways of acknowledging and labeling your feelings — for instance, you might say something like: “I was feeling frustrated about..." or "I'm really excited about..."