Conversation Starters for Friends You Haven’t Seen In a Long Time

Has this ever happened to you? You’re in the subway station, waiting for a train, and you run into an old friend from high school whom you haven’t seen for about 4 years.

Unless you’ve recently moved on the other side of the planet, chances are something like this happens to you every once in a while.

The Old Friends Paradox

I find that many people struggle to start a conversation with an old friend they haven’t seen for a while. They may have been really close once but as the time passed, the emotional connection faded, and the common ground between them narrowed.

You have different lives now; you’re not used with seeing each other anymore. This can create an awkward feeling and a lack of momentum when meeting an old friend, either intentionally or by accident.

Conversation Starters for Old Friends

In such contexts, there are always good conversation starters you can rely on to get the conversation going. Here are some of the most valuable conversation starters for friends you haven’t seen in a long time:

1. How have you been? What have you done? Conversations with old friends are a good opportunity to catch up on things. Since a lot of time has passed since you’ve last seen each other, use conversation starters in the form of questions about what happened in the friends’ life during this time.

2. Job and family. If you want to use more specific questions to find out about your old friend’s life, there are two evergreen areas which you can explore: the job and the family. Consider question such as: “Where do you work?”, “What do you do?”, “What’s that like?”, “Are you in a relationships?”, “Do you have kids?” etc.

3. The good old days. I’m not a big fan of dwelling on the past, but every once in a while, it’s good to remember the fun shared experiences from the past with an old friend from that past. It brings that sense of bonding back. So, use convo starters in the form of “Do you remember when…?

4. The common acquaintances. I am also not a big fan of talking about other people’s lives. However, meeting an old friend can be a good opportunity to find out about other friends or acquaintances you both know which you’ve lost touch with. Just make sure you ask about the lives of people you actually give a damn about.

5. Remember old dreams. On out of the box way to initiate a conversation with an old friend is to ask them about the dreams you know they had in the old days and what’s going on with them right now. For example: “I know you wanted to have you own business in high school. How’s that going?

Such questions can be tricky because you may dig up a bad memory of an abandoned dream, but they can also be a chance to find out some good news and build some connection. I think it’s definitely worth trying this approach.

I know many cases when old friendships got brought to live again by one interaction after a long time and both parts were very excited about this. If this doesn’t happen, at least you still get a positive, enjoyable conversation.