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5 Rules for Dating Again at Midlife and Beyond

Copyright 2014 Roberta Gallagher

I have been there both in my 50’s and 60’s and totally get what the struggles of dating are as we age. My Grandma became a widow at 66. She said “Robertala* (my attempt at a Yiddish accent) your heart never gets old.” She fell madly in love with Louis at 68.

Grandpa was a great man. I’m guessing this was an arranged match. Grandma was beautiful but not so bright and Grandpa was super smart and not so beautiful. Louie was a charmer and we all thought he was disingenious. None of us trusted him and made sure she couldn’t write him any checks. Your children become your parent.

When first dating after being in a long term relationship, the first OMG is how different the world is than the one you were in when last single. It’s weird but being in a relationship can be a time warp. The latest cultural changes when in the flow of change are subtle.

But now it is traumatic and disorienting as you experience change all at once. The process of dating brings up the insecurities of adolescence. “Am I going to be popular?” Will I get responses from my photo and bio on dating sites?

These days there are special sites for older adults which can make you more more comfortable.

Now some practical advice:

1. Be yourself.

Unless you absolutely have distancing personality traits there is no need to change. Don’t dress to be accepted. Dress like yourself. That is who you will continue to be. Don’t you want someone to be attracted to the genuine you and not a figment of who you think they want?

2. Brush up on popular culture.

Become conversant in political and moral issues. Discover your own opinions and find someone who feels the same. It is difficult enough to be in a relationship when you have similar values. If you don’t it’s fraught with conflict.

3. Do not be desperate.

You can’t fit a square peg into a round hole. Most of us want to be in a relationship. It is from personal experience I advise you; there is more to a match than the way a person looks. If you like foreign films, classical music and are politically progressive you may well be attracted to your opposite. If the possible mate likes Country Music, horror movies and is ignorant or very conservative politically it will not work long term.

4. It’s okay to have exciting experience

That includes sex even if the person does not fit marriage criteria. This is a time for learning about yourself and new experiences add to self knowledge. Caveat: don’t delude yourself into believing that this Is it. Be smart about your experiences.

5. It can be helpful to like their family.

And for your family to like the other person. This stage of life Is about being your own person and questioning the constrictions of the past.

Get comfortable with stretching your boundaries. Life is too short to approach dating as a task rather than an adventure. Have fun!

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