Is Socializing Awkward Now? Here’s How to Have Meaningful Conversations Again

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I’m dubbing it the friendship gap: The vortex of time that occurred somewhere between the start of the pandemic (when the Zoom sessions tapered off) and the present day. In some cases, it’s been actual years since you’ve seen pals you once considered close in person and, well, the reunions can feel awkward. Because how on earth do you attempt to sum up—or catch up—on the hell we’ve all been living through for the past two years?

Personally, I’ve leaned on small talk. But is there a way to have meaningful conversations again? We chatted with Celeste Headlee, author of We Need to Talk: How to Have Conversations That Matter—and the upcoming book Speaking of Race: Why Everybody Needs to Talk About Racism and How To Do It—about where to start.

1. It’s OK to Skip the Part About the Pandemic

When you do finally reconnect, Headlee says it’s OK to consider your months of solitude a wash. “Do not feel the need to catch up on all the time that has passed,” she says. “It’s fine to kick things off with, ‘It’s been a long time since I’ve seen you, can you give me a recent update? What’s happened in your life in the past few weeks?” If you want to get more specific, she recommends saying: What’s something good that’s happened recently? (Headlee says this tactic can lift the mood of the person you’re talking with and improve openness.)

2. Small Talk Is Also Normal—and Encouraged

“Ask people about the books they’ve been reading, the TV shows they’ve been binging, any new foods they’ve tried in the past year,” she says. Sticking your toe in with light topics is a good thing. If it moves on to more serious topics, fine, but it’s OK to let conversations center on non-stressful common ground.

3. Awkward Re-Entry Doesn’t Mean the Relationship Is Broken

It can certainly feel strange when you can’t easily pick up where you left off. But that doesn’t mean you should automatically give up on a friendship. It’s more that you might need more time to peel back the layers. Headlee suggests starting with empathy. “The most important thing when you’re trying to talk about any kind of trauma—which everyone has suffered from to a greater or lesser degree during this time—is to not focus on what you want to say, but on what you want to hear,” she says. In other words, prioritize listening and asking follow up questions. (You say, ‘How are things going?’ They say, ‘Not bad.’ You say, ‘Not bad can mean a lot of things. What do you mean?’) This doesn’t mean you won’t eventually get to share your own experiences, but giving them the space first can make it easier to be honest and authentic.

4. Prioritize Truthfulness

When a friend asks, ‘How’s work?’ but it’s not going well, it’s OK to say: “You know, it’s not going great, but I’m keeping my head above water.” (This keeps things light, but at the same time, sincere.) “One of the biggest barriers to meaningful conversation is when we’re not truthful about our feelings and our thoughts,” Headlee says. People can sense when they’re not being told the truth. “They just don’t know specifically which thing was untrue, which results in a more cautious interaction.”

5. Personalize Your Ice Breakers

When you finally do catch up, take time to really notice the other person—has their hair changed? What are they wearing? Can you get a sense of their mood? If they’re dressed differently, you can try: ‘You know, I don’t plan on wearing jeans ever again. Did you change the way you dressed over the past couple of years?” If you’re catching up between other meetings, you could say, ‘How are you handling all the Zoom calls?’ or ‘Talk to me about those fabulous bookshelves behind you.’ The best conversations rely on paying attention first. If you’re present and engaged, it should flow from there.

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Rachel Bowie

Royal family expert, a cappella alum, mom

Rachel Bowie is Senior Director of Special Projects & Royals at PureWow, where she covers parenting, fashion, wellness and money in addition to overseeing initiatives within...
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