The answer is Yes and No.

In many ways, dating is dating. There is a courtship process. That is, two people getting to know each other and finding what they have in common. Whether you are in your 20’s, 30’s, 40’s, 50’s, 60’s or more, dating is about building a  level of communication mentally, intellectually, spiritually, and often financially.

However, perhaps one major difference in dating between your 20’s and your 50’s is how you plan for the future, perceive the future, and share ideas about the future. Often, for those in their 20’s the concept of growing old, retirement, death, and the like, is so far off in the distance that it feels like a non-issue. In essence, “we’re going to live forever.” Fast forward to those in their 50’s and most of these individuals have most likely experienced that “ah-ha” that at some point life will come to an end and how we deal with this reality becomes more important.

Therefore, the conversations between twenty somethings and those in their fifties are often different. Focus on the future is different.

A second major difference could be that of physical aging. It’s easy to recognize a person in their twenties. However, individuals in their 50’s and 60’s (and over) can look much older, younger, or physically reflect their current age. Depending on diet, exercise, mental attitude, and levels of life stress, the aging factor can affect who you attract, what you talk about, and compatibility.

When I was giving a presentation at the Hyatt Park Lane, a retirement community for older citizens, I recall a gentleman in the audience who was ninety-nine and getting married to a women age seventy.  His fiancé was much younger but that didn’t bother her because they had so much in common and she didn’t mind settling down to a quieter lifestyle.

A single woman at twenty-two chose to visit E-Harmony. She was looking for someone that was fun, humorous, could create a stable career, was physically active, loved animals and wanted to travel. She also wanted someone in her age bracket. Therefore how she viewed a future relationship was much different from the previous example.

Putting aside these two different perspectives related to age, it is interesting to note what helps successful dating, and what makes these relationships work.

Here’s a good tip to get started whether you are twenty or ninety:


Whether you are twenty or ninety, knowing what makes you happy and optimistic about the future is key.

This helps you to ask for what you want in a dating situation and come across as honest, sincere, and interesting. It allows you to ask good questions and respond authentically. Here is a simple exercise that helps. I call it, Understanding Your Needs and Wants to navigate the dating scene.

Rate the Choices in an order of top priority – to low priority – 1 – 26. For instance, children might be rated as #1 or, animals might be rated as #1, or, fitness might be rated as #1. What’s of second importance? Continue to rate in order of what is most important to you.  If you come up with other choices that match your personality, put those on the list.


Money                                     1.__________________________________

Success                                    2.__________________________________

Power                                      3.__________________________________

Freedom                                  4.__________________________________

Security                                   5.__________________________________

Fame/Recognition                   6.__________________________________

Love/Marriage                         7.__________________________________

Children                                  8.__________________________________

Creative/Artistic Expression   9.__________________________________

Travel                                      10._________________________________

God/Faith/ Spirituality            11._________________________________

Adventure                               12._________________________________

Fitness                                     13._________________________________

Risk Taking                             14._________________________________

Cooking                                  15._________________________________

Nature                                     16._________________________________

Socializing                               17._________________________________

Time Alone                             18._________________________________

Volunteering                           19._________________________________

Teaching                                  20._________________________________

Motors/Cars/Planes/Engines   21._________________________________

Animals                                   22._________________________________

Healing/Meditation/Psychic    23._________________________________

Movies and Fun                      24._________________________________

Sensuality                                25._________________________________

Family                                     26._________________________________


What did you come up with?

NOW, let’s look at some STOPPERS that can prevent you from following through with the list you’ve just created. 

Rate yourself on what you think might prevent you from presenting yourself in the best light, genuinely and with ease.


Past Embarrassments              1._________________________________

Critical Thinking                     2._________________________________

Fear of Rejection                    3._________________________________

Family Issues                          4._________________________________

Overly Judgmental                  5._________________________________

Vanity                                     6._________________________________

Jealousy                                   7._________________________________

Not Noticing Dating Clues     8._________________________________

Addictive Behaviors               9._________________________________

Needy                                     10.________________________________

Self Absorbed                         11.________________________________

Smothering                              12.________________________________

Starry Eyed/Infatuation          13.________________________________

Over Thinking                         14.________________________________

Past Partner Attachments       l5.________________________________


If you relate to any of these points, you may want to read my published articles “What Brings Happiness” and “Simplifying Successful Relationships: the Intimacy and Dating Scale.”

Awareness of our strong points is important. Awareness of our weak points is a prerequisite for understanding why dating strategies may or may not be working. Is there something you want to change about how you interact with others? Are there some stoppers you want to let go of, or unlearn?

Being happy in a relationship can be brought down to a core thought: Choose a person who can become your best friend for life and who understands your personality, quirks, and interests. Someone you put first, and they put you first.

Successful dating in your 20’s and 50’s is about being yourself and finding a person who understands you and your personal values. The “Stoppers” seem to melt away because they do not enhance the relationship. Or, they aren’t a part of your dating etiquette to disrupt the courtship process.

Our choices form our outcomes. Nurturing a burgeoning relationship can be likened to lighting a candle wick and seeing how brightly it burns. If you get no spark and the wax doesn’t fuel the flame, likely this relationship will be put into “the friend zone” or there will be a simple and polite “goodbye.”

I have met so many thousands of individuals who found a life partner when they were least expecting the person to walk into their life, whether at twenty or fifty. The dating process started on an elevator, or switching planes, or care-taking for a friend’s cat, or selling a product, or fixing a tire on the side of the road, or traveling to another country, or walking by a gallery and chatting about art…the list goes on and on.

Now let’s look at another dating tip.



  • Gossiping
  • Ignoring your inner voice, inner desires and feelings
  • Over talking
  • Not accepting compliments
  • Being late
  • Taking others for granted
  • Overspending
  • Not taking time to enjoy the moment
  • Being Rude
  • Giving away your power
  • Lying to yourself


  • Being yourself
  • Choosing to do things you like
  • Listen
  • Sharing your talents and goals
  • Being spontaneous
  • Allowing for together time and still have private time
  • Speaking your truth
  • Noticing what works
  • Honoring your word
  • Forgiving any misunderstanding
  • Making love within your timing and your comfort zone
  • Following through
  • Understanding commitment

I’ve discovered not only in my life, but with so many thousands of others, love FINDS US. Enjoy these tips and I believe the person you are searching for will enter your life. Let the courtship process begin.

NOTE: Please let me share that many of my clients, men and women alike have decided not to date anymore. They are happier being single. If this is your choice I support you. There is no rule that you have to be in a relationship.

In conclusion, is there a difference between dating in our 20’s or our 50’s?  Yes and No.

Perception changes and evolves with age. However, what makes the dating process successful and leads to lasting love usually rests on being happy. When you are dating, ask yourself these questions: Can I count on this person and does this person give back equally? Do I enjoy this person? Can I trust this person? Can I grow older with this person and remain happy? Am I my best self with this person?

Shows like “The Apprentice” that invite divisive, competitive, and back-stabbing behaviors to “win” aren’t real life. That’s why “The Apprentice” is called a television show. It is pure entertainment. Like they say on “Myth Busters”… “Don’t try television entertainment tactics at home.”