Why making new friends in retirement feels so awkward
We talk a lot about how hard it is to make friends as an adult. But we don’t talk nearly enough about how much harder it gets in retirement — when work is no longer a built-in source of social connection, your routine shifts completely, and your social landscape changes almost overnight.
If you’re feeling this, you’re not alone. And you’re definitely not weird for struggling with it.
For years, work helped structure our friendships — casual hallway chats, birthday cake in the break room, group lunches on Fridays. That environment made it easier to meet people and feel connected, even if the friendships weren’t all deep. But when retirement comes, that entire structure disappears. Suddenly, you’ve got more time… but fewer natural opportunities to meet people.
Some people expect to spend more time with old friends in retirement, but those plans don’t always pan out. Maybe your friends are still working and don’t have the same flexibility you do. Maybe your closest friends live in another city. Or maybe you downsized to a quieter, more affordable area and left your old community behind.
And starting over socially is hard — especially later in life. It takes energy and vulnerability, and sometimes, it just feels plain awkward.
You might worry that people already have their friend groups. You might feel shy about joining a class or group on your own. You might go to an event and feel like the odd one out. Or you might meet someone nice and then wonder, Do I text them? Do we grab coffee? Was that just a one-time chat?
It can feel a bit like dating. And that’s not something most people expect in retirement.
But here’s the thing: it’s completely normal.
This stage of life comes with huge transitions. And just like when you moved to a new city in your 20s or when your kids started school and you met other parents — it takes time to find your people again. It takes effort, too. But the effort is worth it.
Here are a few ways to ease the awkwardness and increase your chances of making friendships that feel natural and enjoyable:
1. Start with shared context. Join groups or attend events that naturally align with your interests, values, or personality. If you love books, try a local or online book club. If you like walking, see if there’s a free local walking group. If you’re spiritual or community-oriented, check with a local church, mosque, or community centre. The more shared context you have, the easier the conversation tends to flow.
2. Go for low-pressure consistency. Instead of trying to spark instant connections, aim to just show up. Visit the same café at the same time each week. Attend the same free activity or event regularly. Familiarity creates comfort — and often leads to conversation over time.
3. Acknowledge the awkwardness, but don’t let it stop you. It’s okay if you feel a bit unsure or rusty. Most people do. Think of this as a skill you’re re-learning, not something you’ve failed at. Even introducing yourself to one person or saying “see you next week” at the end of a class is progress.
4. Be honest with yourself about the kind of connection you want. Are you craving deep friendship? Or are you just looking for someone to share an activity with each week? Not every new acquaintance has to be a lifelong best friend. Sometimes, a walking partner or someone to chat with over tea is exactly what you need.
5. If budget is a barrier, look for free or low-cost options. There are more than you might think. Libraries, councils, charities, and local community groups often run free sessions. Or try something online if getting out feels like too much at first.
6. Let tech help you. At LivOn, we’re building tools to make this easier — suggesting opportunities that match your interests and personality, and letting you connect anonymously with others navigating the same phase of life.
Making new friends after 60 isn’t always easy. But it is possible. And it starts with something small: showing up, staying curious, and remembering that so many others are feeling the same thing you are.
You don’t need a huge circle. You just need one or two people who get you.
And often, that kind of connection begins with a simple, brave yes.