How to Deepen Your Relationships (And Make New Ones!) Through Meaningful Conversation

Anna Sale Headshot

We spoke to podcaster and author Anna Sale about how to deepen your relationships by talking about tough subjects.

We’ve all been in a situation where we just don’t know what to say. Maybe you have a friend whose brother just passed away, maybe your coworker is getting divorced, maybe your neighbor just found out she has cancer.

Whatever the specifics, there are times when we don’t want to say the wrong thing — so we don’t say anything at all. Anna Sale, host of the beloved WNYC podcast Death, Sex, & Money has just written a new book called Let’s Talk About Hard Things, and wants to teach us to do just that. We spoke with Anna about how to make new friends, what to say to someone who’s going through a hard time, and how to find connection when you’re feeling lonely. 

KCM: How do you break the barrier in small talk to get to a more meaningful conversation — without it feeling jarring? 

This is a practice that we can all try out right now, because we’ve all been through something big, and now we’re being thrown back together. What are those catch-up conversations going to look like? First, consider if you feel comfortable being the first one to share, even if it’s a short sentence that shows you’re willing to go deeper. Maybe it’s something like, “I have two little kids, and I’m really exhausted,” something like that. 

Once one person in a conversation leaves the small-talk script, it indicates that they’re willing to talk about something a little bit less clean and tied up. Often, the other person will reciprocate.  If they need to talk, that gives them an opening. It’s really just about paying attention and listening. Be willing to go off-script. That short exchange may create an opening to come back to harder topics.

Do you have any suggestions for how to make new friends, especially for those of us who might be a little rusty?

Making new friends is a bit like dating: You really have to put yourself out there, and that can feel weird! Say you meet someone at the dog park and want to grab coffee with them… what do you talk about? A lot of us won’t take that extra step to ask to get coffee because it feels awkward, but when you find those little moments of connection with someone, try to push yourself to follow up. Just say something like, “It was so great to meet you, would you want to have lunch sometime?”

I understand that the struggle is real. Most of us don’t have a lot of leisure time. But if you feel a friend connection with someone, try to make the most of that opportunity. You also might be surprised by who your new friend could be. I just made a new neighborhood friend who’s a 75-year -old grandma. We sat on her deck this week and talked about life. It was the most fun I’ve had with a friend in a long time. 

Can you give some examples of things to say to people who you know are going through something difficult: the loss of a loved one, a divorce, etc? 

I totally understand the impulse to say something that will comfort someone who’s struggling. I have that impulse, too. You want to tell someone they’re going to feel better, but often that’s not the right thing to say. I’d suggest something like, “I care so much about you and I’m so sorry that you’re going through this.” If someone is grieving a lost loved one, it’s always nice to share what you remember about that person and what they meant to you. There’s also great importance in making a commitment to keep checking in on someone, because big, difficult topics aren’t going to be fixed in one conversation. 

Commit to checking in on someone every couple of weeks. In the book, I talk about a woman who lost her partner to a sudden drowning. She had a friend who said, “I really am worried about you, and I don’t want to make you feel like you have to talk to me every time I call, but I also want to know you’re OK, even if you’re just taking time by yourself.” So they created a system where her friend would just text to check-in and say, “Can you send back an asterisk just to tell me you’re there, if you don’t want to talk?” It’s a simple way not to force conversation for someone who’s grieving and might not have the energy to talk about it, but will let them know you’re there for them. 

What happens if a conversation about a hard thing goes south — if you feel like you’ve overshared or made the person uncomfortable, or vice versa?

I think it’s about paying attention in the moment. Often you can tell if you’ve gone one step too far, either because it’s an inconvenient time for the person you’re talking to, it’s bringing up something that they’re not ready to talk about, or if they’re just overwhelmed by your feelings and can’t take them on. If you feel that happening, you can say something like, “Wow, I didn’t realize I had such strong feelings about this! Let’s continue this conversation another time, but thank you for listening.” You can indicate that you notice how the conversation is going, so afterwards you don’t have to feel like, “Oh my gosh, that was so clumsy and messy.”

If someone overshares with you and it’s more than you can take on, or you don’t have the time to devote to a heavier conversation, I suggest saying something like, “I didn’t know you were going through all that. I’m so sorry. This actually isn’t a great time for me to talk, but thank you for sharing that with me. I’m going to be thinking about you.” That’s a way to gracefully draw that boundary.

If you’re lonely, how do you begin to reach out to people and say, “I need connection?” 

I think it’s about saying that very thing. It’s really important to start any conversation about something tender or personal by saying something like, “I need to talk to you about something. Is now a good time?” That way you’re signaling that this is going to be a different kind of conversation. You’re preparing the person you’re talking to that they may need to carve out some time to give you attention. Hopefully, this will also prepare them to slow down and listen in a different way. I think the scariest part is reaching out — letting someone know that you’re having a hard time and you need to talk. Even if these conversations are slightly awkward, the alternative is to pretend that you’re not burdened and to feel really isolated and alone.

Giving yourself permission to admit that is hard work, but you’ll no longer be going through it alone. You’re also reinforcing the relationship that you have with this person — you’re creating a stronger relationship that is going to carry forward for you both. I opened my book with a quote from one of my best friends, Ann Simpson, who’s now 89 years old. She says, “Openness creates openness.” It’s so simple. Instead of thinking, “I’m so scared to look like I don’t have my life together and I have to admit this embarrassing thing,” you think of it as, “I’m just going to be open,” you may be surprised by what comes back to you. 

Written by Emily Pinto

This interview has been edited and condensed