How to Check in on Your Friendships

You know your best friend’s coffee order, complicated family dynamics, and feelings about her boss. But you might not know whether she wishes you called more—or how much she appreciated that text you sent last week.“We have this expectation that friendships should be easy, that we should always be affirmed, that our friends are kind of there forever,” says Nick Fager, a therapist in New York. Yet the people you want in your life for the long haul need care and attention. That’s why he encourages clients to do friendship check-ins: brief conversations about how things are going between you, including what you appreciate and what could use a little work.These chats can help you identify hurt feelings before they turn into resentment, figure out how to support each other through changes, and say the lovely things you’ve been thinking but haven’t actually shared. They can also be fun. “A check-in should involve laughter,” Fager says.To try it, choose a relaxed moment—on a walk or over coffee—and start by telling your friend how much they mean to you, suggests Janine O’Brien, a clinical psychologist in New York. Explain that you’d love to check in about how you can keep being good friends to each other. Pick one question to start with, give each other room to answer, and resist the urge to immediately defend yourself if something uncomfortable comes up.We asked friendship experts which questions are worth making time for—and why.“What’s working for you in this friendship right now?”Maybe your friend can make you laugh on a day when absolutely nothing is funny. Or she remembers when you’re waiting on medical test results and checks in. You appreciate it. Does she know that?“We love so many things about our friends that we don’t actually tell them,” Fager says. “When’s the last time you told them exactly what you love about them?”Starting with what’s good gives you both a chance to feel appreciated—and makes it easier to talk about anything that’s been bothering you. Be specific: You love that she makes the plans, that you can tell her embarrassing things, or that she’s kept the same ridiculous inside joke alive for 15 years.Friendship check-ins shouldn’t only happen when there’s something to fix, O’Brien adds. “It’s important to also be able to say what you appreciate in the relationship and what’s working well,” she says. Over time, that can help you feel more comfortable expressing disappointment or hurt, too.You think your monthly phone calls are keeping the friendship humming along. Your friend misses when you talked every week. Neither of you knows there’s a mismatch, because you’ve both been assuming the other person feels the same way.By asking this question, Fager says, you’ll find out. You might discover that you’re both perfectly happy with how often you connect; or, your friend might finally admit they’ve been missing you. For example, Fager says, a friend might say: “We used to hang out a lot more before you had your kid, and now it’s less. Could we maybe try to do a little bit more?”You can also talk about who’s doing the reaching out. If you’re always the one suggesting dinner, it’s easy to wonder whether you’d ever see each other if you stopped asking. Your friend, meanwhile, might have no idea you mind being the designated planner.Once you know how you each feel, you can figure out what’s realistic. Maybe that means a standing call, more voice notes, or taking turns organizing your next get-together. You might not be able to talk every day, but you can make sure neither of you is left wondering where the other stands.“I’m not going anywhere.”Sometimes, your friend knows she hasn’t been calling enough. She’s also raising young kids, taking care of her aging dad, or barely keeping up with work—and worrying that you’re upset with her is one more thing weighing on her.When a close friend was busy with two young children during the pandemic, friendship expert Anna Goldfarb, author of Modern Friendship, wanted to take that worry away. As they sat down at a restaurant, she reassured her that she understood how busy she was.“I know you think about me all the time. I think about you all the time too,” she told her. “My door is always open for you.”Her friend’s shoulders dropped, Goldfarb recalls. She didn’t have to find more time to spend together or apologize for not having it.“Instead, the strategy I chose was just certainty,” Goldfarb says. “I’m not going anywhere. You’re still my best friend, and it’s OK if we don’t talk.”“Have there been any moments recently between us that you’d like to revisit?”That joke at dinner stung. Or your friend seemed distracted when you were telling her something important, and you’ve been wondering whether to bring it up ever since. By now, it might feel like you’ve missed your chance.You haven’t: This question makes room to return to something you didn’t know how to address in the moment. Otherwise, Fager says, “we end up just stewing on it and then distancing ourselves." Or we tell another friend what happened—and the person who could actually help clear things up never hears about it.Even close friends hurt each other’s feelings without meaning to, Fager says. Asking about those moments lets your friend know it’s OK to bring them up—and that you’re willing to listen.If you’re the one asking, let your friend finish before explaining what you meant. Listen, acknowledge what hurt, and apologize when appropriate. You can also return to the conversation if you realize later that there’s more you want to say. As Fager puts it: “The check-in is not everything.” Part of its purpose is to make the next honest conversation easier.“How do you feel that you’ve changed recently, and how can I support you in that?”Your college drinking buddy doesn’t drink anymore. The friend who used to close down every party now wants to leave by 9. You’re happy to reminisce about who you were together—but how much do you know about who she is now?“We often want the person to stay in a certain version of themselves because it reminds us of a certain phase of life,” Fager says. That version might be especially fun, or familiar, or easy to connect with. Still, holding someone to it can leave them feeling like there’s little room to grow.Asking what’s changed gives your friend a chance to tell you about a shift you might not have noticed. Someone who’s given up alcohol, for example, might want to rethink where you hang out or explain what kind of support would help, Fager notes.You can still remember old adventures—while making room for new ones. “It’s important to also recognize that things have shifted,” he says.“Is there anything happening in your life that I can show up better for?”You know your friend’s mother is sick. But does your friend want to talk about it—or would she be more grateful for an invitation to do something that gets her mind off it for a while?O’Brien recommends asking rather than assuming you know what would help. Your friend might need something you hadn’t thought to offer, or want to talk about a problem you didn’t realize she was dealing with. Maybe you’ve been asking about her mother, but no one’s asked how she’s holding up.Give her time to think. “They may not know how to explain the support they need,” Goldfarb says. “They may feel put on the spot.” You can make clear that she doesn’t owe you an answer right away: “You don’t have to know now. I just want you to know you can ask me.”If she’s unsure, try offering something specific: “Would you like some company this weekend?” or “Can I drop off dinner on Tuesday?” That gives your friend something concrete to respond to—and a chance to tell you whether you’re on the right track.“How can we keep each other on track for our goals?”Perhaps your friend wants to finish writing their first book, start running again, or finally launch the newsletter they’ve been talking about. Asking how you can help gives you something meaningful to work on together—and a reason to keep checking in. “Working on a goal is a wonderful, wonderful gift we can give to our friends,” Goldfarb says. “It’s something to talk about.”She recently discussed doing a weekly check-in with a friend about their Substacks: On Fridays, they could text each other about how things were going. That gives their conversations a purpose tied to something they both care about.Ask what kind of involvement your friend would welcome. Maybe she wants someone to celebrate small wins with, read a draft, or join her for a walk while she talks through an idea. Agree on a rhythm that feels useful to both of you, Goldfarb suggests, whether that’s a weekly text or a monthly conversation.“What can we do that’s ours?”“We should get together soon” is an excellent way to end a conversation and a less reliable way to get something on the calendar. Try asking what you’d actually be excited to do together.Goldfarb posed this question to her busy friend after reassuring her that she understood why regular hangouts weren’t realistic. Her friend suggested a birthday slumber party. “Girl, let’s do it,” Goldfarb told her. Their birthdays are both in March, and they’ve now kept the tradition going for several years—with Goldfarb’s husband making himself scarce for the occasion. “He high-tails it to his mom’s house,” she says.Your version could be an annual camping trip, a hike you’ve been meaning to take, or dinner at the restaurant you keep sending each other posts about. Choose something you both want to make time for, even if it happens less often than you once imagined.“Part of the challenge of modern friendship is being flexible and being open to the variety of friendships we get to have,” Goldfarb says. “It’s not better or worse. It’s different.”