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Dating in my late 50s

Advice12/09/202540 Views

The question

Maya, from St John, writes: I’m 58 and single again after a long marriage. I’m not sure if I want to date, but I also feel lonely sometimes. Is it possible to build meaningful relationships at this age – romantic or otherwise – and how do I even start?

Your answers

Love at 61 surprised me completely.

David, 62  Toronto, Ontario

Photography classes and local gardening clubs became my essential social foundation long before dating ever entered the picture. Eight months of steadily building genuine friendships created real confidence and completely eliminated any sense of desperation or neediness.

Patricia, 55  Vancouver, British Columbia

I spent a full year rediscovering my personal identity through solo travel, learning woodworking, and reconnecting with old friends I’d lost touch with during married life. Learning to genuinely enjoy solitude proved to be essential preparation for any future relationship.

James, 59 Boston, Massachusetts

Book clubs, weekly walking groups, and beginner line dancing classes introduced me to wonderful people without any romantic pressure or expectations. Deep, lasting friendships enrich daily life just as much as romance does, honestly.

Nadine, 60 Halifax, Nova Scotia

Online dating felt exactly like a series of awkward job interviews. Local history society meetings, photography club outings, and community theater volunteering offered much more natural meeting environments with shared interests providing solid foundation. Two years later, love emerged from the most unlikely place — community theater props department.

William, 64 Cambridge, UK

Post-divorce terror about dating led to an unexpected but brilliant strategy: building a fantastic, fulfilling single life first.

6. Grace, 56 Charlottetown, Prince Edward Island

Small northern towns initially seem quite limiting for meeting people, but meaningful relationships often develop slowly and naturally with folks already in your social orbit.

Arthur, 61 Whitehorse, Yukon

I joined grief support group seeking healing and understanding, definitely not romance. The group gradually became my chosen family, offering profound friendships that sustain me through daily challenges and joys. A romantic relationship did eventually develop with another member, but the deeper treasure was learning that loving family can absolutely be created at any stage of life.

Eleanor, 63 Atlanta, Georgia

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