Expert Tips for Avoiding Awkward Conversations with Old Friends

updated May 24, 2019
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(Image credit: Alexis Buryk)

From the first high school reunion to the last September wedding, a quick coffee catch-up to a boozy brunch with old friends, summer is the season for reconnecting with people from your past. But what’s the best way to get back into the flow with someone you haven’t seen in a while?

British authors Judy Apps and Catherine Blyth have mastered the art of conversation — in fact, they’ve both written books by that very name. Apps’ The Art of Conversation coaches the reluctant or anxious conversationalist to speak thoughtfully and listen empathetically, while Blyth’s book, also titled The Art of Conversation, draws upon history, philosophy, literature, and Blyth’s own cunning sense of humor to enumerate the elements of successful conversations — and the traps that ensnare them.

I spoke separately over the phone with Apps and Blyth to learn their tips for reengaging with old friends over a meal. Both women were warm, witty, and easy to open up to, and said that genuine interest and a relaxed attitude are key to chatting fluidly.

6 Tips for Making Conversation with an Old Friend

1. Show a little love.

“It may seem really obvious,” says Blyth, “but if you’re really happy to see someone, make sure you show it. Warmth and directness and a big hug and a big smile. Or just say, ‘Oh, it’s so good to see you!’ Things like that are always worth saying out loud. Marking out that safe space, just reminding them how pleased you are to be with them, is the opening gate to any good conversation.”

2. Start with small talk.

“The safe topics are things that don’t look you eye and say, ‘So what about you? What do you think, what have you done, what have you achieved?'” says Apps. “If you ask people about good things, you’ll probably get the best of them.” Here are a few conversation starters.

  • What are you enjoying at the moment?
  • What’s been good for you this year?
  • It’s been 10 years since I saw you — what are the highlights for you?

3. Tread lightly over old news.

Although it’s tempting to ask if someone is still doing something — So, are you still in HR? — this is actually “the worst question in the world when someone has moved on, or they’ve failed, or their life’s completely changed,” says Apps. “If it’s been quite a long time, so many of us are not the person we were before.”

4. Get out of the past tense.

Instead of lingering in the past, Blyth suggests talking about what’s happening now — or what’s happening next. “That’s what we’re all really most interested in,” she observes. “A small but bland question like ‘What are you doing tomorrow?’ very easily leads to a very intimate place, like plans and hopes.” Then, she adds, “you can dig deeper.”

5. Don’t be afraid of a little controversy.

If you’re concerned about talking politics this summer, take heart: Both women believe that controversy makes excellent fodder for conversation. A good way to dive into a hot topic is to ask a question, suggests Catherine. You don’t have to agree on everything; it’s more about finding things that are relevant to both of you. Try these questions.

  • Have you seen the news?
  • Can you believe it?
  • What do you think?

The key to disagreement, adds Apps, is “keeping the rapport with somebody, keeping the friendship, and being happy to say, ‘Well, wow, isn’t that interesting! That isn’t what I think at all.'”

6. Follow the flow and be ready for anything.

Above all, don’t try too hard. “The best conversation is one where you’re connecting with someone and surprised by the turn of thought,” says Blyth. “You want to keep things fresh and spontaneous.”

Apps agrees: “I think it’s a matter of being ready for life to be interesting. When you go to a dinner party with people you haven’t met in a long while, it’s going to be interesting. Don’t expect it to be the same — be delighted for whatever comes up.”

What’s your best advice for catching up with someone you haven’t seen in a while?