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Dating in Your 50’s

Women Talking gives us tips on dating in your 50’s- “whether you’ve been dating for decades or you’re just re-entering the mature dating scene, it is a natural process that should never be feared.

Dating can seem pretty daunting at any age but as we mature we adopt a different outlook to life. However the basic principles of dating rarely alter.

The experience also means different things to different people, particularly across generations. The relationship may be sexual, but it does not have to be. It may be serious or casual, straight or gay, monogamous or open, short-term or long-term. All in all dating is a form of courtship consisting of social activities done by two people with the aim of assessing the others suitability as a partner.

Mature Dating is still about getting to know someone, taking the time to see if you connect spiritually, emotionally, intellectually and physically. Above all else, communication remains key.


Always be yourself, smile, keep an open mind, and be honest. Be able to identify your strengths and weaknesses and know what you’re looking for in a relationship.

Perhaps the greatest difference between dating in your twenties and dating in your fifties is the way you identify and interpret the future. The tomorrow’s you once pondered are suddenly the here and now.


You’ve planned for retirement. You might have a family. Aging and death aren’t as distant as they once were. The way you and your date communicate about and focus on the future will dictate compatibility.

A sexual relationship in your more mature years can be just as important now as it was when you were younger. Know your boundaries and values before starting to date someone new. Many older daters feel more sexually liberated and confident than in the days of their inexperienced youth. Others are paralyzed by body issues and sometimes terrified of being with someone new. And some are wrestling with hormonal issues that negatively affect their sex lives. Talking about sex is no longer taboo; expect to have these conversations fairly early on in a new dating relationship.

We all have a past, a history of events and experiences that were positive and negative. From these we learn about the things that make us happy and areas of life we would rather avoid. Take inventory of what time has taught you and learn from past relationships about what you are now searching for.

Try to avoid talking about exes on the first date — or at least mention them only in passing and without bitterness. Bitterness is often the greatest criticism from older daters.

Being too critical in a relationship is something else best avoided. This may seem helpful at first, but over time can be difficult to live with for you or your partner.

Never being satisfied is also another ‘no no’ when dating. These are fundamentally unhappy people and no matter how much you love them, your love will never be enough for them so take life lessons from relationship disappointments and only start to date again when you’re ready to approach someone new with hope and optimism.

There should be no urgency to dating. Be patient with yourself and don’t rush things. Take your time as you reenter the dating scene. If you’re nervous about meeting a stranger for dinner, opt for a daytime date. If you’re overwhelmed by someone’s affections, explain that you need to move slowly.

Don’t higher your expectations to be unreachable. Not every person you date has to be “the one.” Compromises are the key, but of course within reason and ensure that you’re in a relationship for the right reasons. 

When you are ready to start dating, involve other members of your family. Tell your friends you’re ready to meet someone; you never know they may know the perfect match in a similar situation to you and set you up on a date.

Online dating is now the norm, with people getting to know each other online or at least screening each other before that first date. If you’d like to try online dating use sites that are ideal for the more mature dater.


If you have adult children, you might find that the tables have turned, with them now eager to give you dating advice. Involve your family as much as you feel comfortable, this could avoid awkward introductions later.

Take care of yourself, your health and your appearance. You can still be vibrant and youthful in your fifties and sixties and beyond. Aim to be someone you’d want to date.


Images: 1, 2, 3

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