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In 1991 Billy and Akaisha Kaderli retired at the age of 38. Now, into their 4th decade of this financially independent lifestyle, they invite you to take advantage of their wisdom and experience.

Dating after 60: Important Dos and Don'ts of Starting Over

Jeremy Hackman

Most people who date after sixty find that things have changed since their earlier years. There are more options now. There are also more questions to answer. Clear thinking helps people choose what suits them. Here is a clear look at common dos and don’ts for dating at this stage, using simple facts and careful advice.

Let Comfort Lead

Some people who return to the dating world after sixty feel pressure to do what others expect. It may be helpful to stop and wait. Try to move at your own speed. For example, if meeting in person feels too quick, suggest a phone call first. There is nothing wrong with shortening a date or walking away if you feel uneasy.

People should not ignore their own needs. If spending time alone feels right, take a short break. Those who date after loss or after years with a partner move at different speeds. It can help if people tell those they meet that they may need time.

Finding Your Own Path: Relationship Choices After Sixty

People over sixty make new choices in many ways. Some try long-distance relationships so they can keep their routines. Others look for companionship without living together. There are those who give online dating a chance, especially if they want to meet people outside their regular circle.

Others go back to dating after a divorce, or after losing a partner, or even after years focused on work or family. The reasons someone may start over vary, and there is no one right way. The most important thing is making choices that feel comfortable for where you are now.

On Meeting New People

There are several ways to meet people after sixty. Online dating sites are common, but not the only way. Friends and family can give introductions. People sometimes reconnect with someone from long ago. Community centers or shared interest groups work for some. Each path comes with its own pace.

If using online dating, keep personal contact details private until you know someone better. Meet in a public place at first. Trust facts, not only words. Before agreeing to meetings, search for the person’s full name, check public pages, and see if details match.

Talking About the Past

Many people over sixty have strong histories. They may have lost a spouse, have adult children, or carry old hurts. Some talk about these things in the first meeting, while others wait. There is no set rule. It helps not to share too much, too fast.

Ask your date what they want to know, and share as much as feels safe to you. Open talk can help later, especially if you keep seeing each other. You can mention children or past partners in simple terms, but avoid going into deep stories right away. Let comfort grow step by step.

Money and the Dating World After Sixty

Money matters more to many people at this age. Some have set incomes. Others have large changes in wealth, either up or down. If you meet someone who talks about money early on or asks you for help, take a step back. This is not common or safe behavior.

It is wise to pay for your own things at first and to meet in places that are not tied to spending a lot. No one should ask you for help or favors after only a couple of meetings. If this happens, tell someone you trust and stop seeing that person right away.

Dos and Don’ts for Dating After Sixty

Dos

Do take your time before agreeing to meet in person.

Do keep your own habits and interests.

Do trust your feelings if something does not seem right.

Do choose safe meeting spots when you first get together.

Do be honest about your life, likes, and dislikes.

Don’ts

Do not share private details too soon, like how much you earn, where you live, or your family plans.

Do not ignore signs of pressure, like someone rushing you to meet or share more.

Do not feel forced to share about the past if you are not ready.

Do not let others decide what kind of relationship is best for you.

Family and Friends Matter

Support from people you know well can help you spot risks and stay calm. Share your plans for dates with someone you trust. If someone in your close circle has doubts about a new person, listen to their concerns before you take the next step. Input from family can guide you when you feel unsure, but keep in mind that you are the one who will make the call. 

Managing Expectations

Some people who date after sixty will form a new partnership or deep friendship. Others may meet people for dinner, walks, or shared interests without labels. There is no set mark everyone has to meet. Early talks about plans and wants can prevent mix-ups. You can say, “I like spending time together, but I’m not looking to move in or marry right now,” if that’s how you feel.

It is common to meet people with their own habits and family ties. Be clear with your own goals and listen to theirs. People who talk openly, even when there are differences, are likely to have clearer and safer experiences.

Closing Words

Dating after sixty means watching your pace, keeping your comfort in mind, and using steps that fit your needs. Some will find a new partner, while others enjoy seeing new faces without strong ties. Most stay safest when they listen to themselves and move in ways that make sense for their own life. No two people need to do things the same way. The only true rule is to follow what fits. 

 

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About the Authors

 
Billy and Akaisha Kaderli are recognized retirement experts and internationally published authors on topics of finance, medical tourism and world travel. With the wealth of information they share on their award winning website RetireEarlyLifestyle.com, they have been helping people achieve their own retirement dreams since 1991. They wrote the popular books, The Adventurer’s Guide to Early Retirement and Your Retirement Dream IS Possible available on their website bookstore or on Amazon.com.

contact Billy and Akaisha at theguide@retireearlylifestyle.com

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