Maintaining The New Senior First Date

Senior Dating

Maintaining the New Senior First Date

David O'Brien

Written by: David O'Brien

David O'Brien

David O'Brien is the author of "Over 50 Dating Secrets," which is the definitive dating guide for mature singles. He also is the co-creator of, which offers an expanded library of senior dating articles. His ebook is available on Follow David on Facebook or YouTube.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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With the old favorite dinner for two no longer our best bet for first date success, it’s time for you mature gents and ladies to act your age.

It’s time for you single seniors to put your life experience to work and also embrace the most basic of modern dating technology.

Yes, even Cupid has come of age.

Unless your objective is 50 first dates, those of us looking to ride off into the sunset with our geriatric Cinderella or Prince Charming need a new dating game plan.

If your last first date was one of your fondest memories of the ’70s or ’80s, be forewarned that dating over 50 is not simply a matter of turning back the clock.

This senior dating thing is not like the proverbial riding a bicycle. Times have changed and so must you – just a little.

So with the clock no longer our friend, how do we avoid a lot of failed first dates and skip right to the part where we have a good chance to find our last true love?

There is no such sure thing, but we can definitely date smarter and put quality ahead of quantity.

In part one, we reinvented the first date, which still involves dialogue and a phase of getting to know one another, just like the customary dinner date, but doesn’t involve food in any way.

Introducing the new cupid:

Instead, the first date is now all about wowing him or her into continuing the courting process because you have already decided he or she was worthy of dating.

The next step before meeting in person? Is he or she worthy of being your mate? Here’s where your new age preparation and creativity become part of the process.

To save lots of time and failed first dates, you need to join the computer age. I see you cringing, but it is easier than you dread.

Without this new tool, you are at a serious disadvantage compared to newly retired boomers who bring the basics of the cyber age with them.

For all you types who aren’t tech savvy, here are the simple steps involved:

1. Buy a cheap computer

Get a basic laptop for portability, even if it is a refurbished model.

2. You’ve got mail

If not you, have someone you know set up a free Google Gmail account or Outlook Hotmail email and learn how easy it is to send and receive email. Email will become your senior dating safety net.

3. Start surfing

Learn how to use Google, Yahoo or Bing to surf the Internet. You are about to join the ranks (age 50+) of the fastest growing users of online dating sites. I see you cringing again, but with some precautions, it is easy and it works.

4. Set your sites

Do an Internet search for “over 50 dating sites” and make a list of at least three that peak your interest.

“At the very least, the dinner

out can wait a date or two.”

5. Get familiar

Navigate through these sites and become familiar with them, how they function and adhere to their safety dating advice.

6. Join for free

Become a free member of these sites and before you spend a penny on user fees, check out how busy the over 50 dating section is in your community. Do not post a picture or contact information other than your city or town and the basic profile info options.

7. Make a minimum investment

Purchase a basic membership so you can connect with singles in the cyber world whose profile and stated interests appeal to you.

Quality sites have an internal email system you can use anonymously until it’s time to use your own email to take the relationship to the next step.

Emails can be revealing.

When you have done some connecting with others (who says it only has to be one at a time?) and you feel you might like to meet someone in person, you can move to the next step of cyber dating.

But remember these precautions:

  • Do not provide business or personal contact information – just an email address you can change or delete any time.
  • Don’t rush or be rushed by anyone. You are still both in the audition phase.

Now that you are off-site and communicating in a more personal and intimate environment, you have the means to discover if this person is truly date worthy.

Here’s how:

  • Personal questions

What personal questions did you not ask on the dating site, such as family and personal interests or future plans to establish if you are compatible?

  • Exploratory questions

Ask questions that reveal character and values, such as, “What would your friends list as your best qualities?” or “Other than family, who did you most admire growing up and why?”

  • Get specific

Find out what he or she is looking for in a relationship and partner. Are you compatible with him or her?

Finally, ask all the questions you need to establish that you want to meet in person or not go any further. It’s much easier this way to move on to the next dating candidate compared to a face-to-face rejection.

When these tools are used correctly:

  1. You will know enough about this person to feel good about a date in the real world.
  2. You will know this person is worth wowing on your first date.

You now have the information you need, based on mutual interests, to set up a fun first date the two of you will enjoy. At the very least, the dinner out can wait a date or two.

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