Photo for the article Internet Dating for Seniors Is a Whole New Ball Game

For the past few years, I have engaged with members of the opposite sex in hopes of settling into an exclusive, long-term relationship. I enter this endeavor in my 6th decade of life and would like to share with you the “rules of engagement” for those who have reached this plateau—and how internet dating for seniors has changed everything.

First off, we are talking about people who probably are divorced or widowed and have gone through their mourning and healing process (usually three years) to get their mental, emotional, physical, and spiritual lives equalized.

Once you have become equalized, in your mind, it is time to strike out and see what is around, available, and authentic. The first thing that strikes you is all the dating norms that were in place when you were in your 20s no longer exist in your 50s or 60s.

Why is dating so challenging for older adults today?

  • There are no singles bars for the 50+ generation.
  • Networking through friends is difficult as most are married, and many of those who would recommend you also are married.
  • You are “that boomer” in the office, and anyway, HR frowns on co-workers dating.
  • Your relatives just laugh at the concept of you dating again.
  • Your children are more concerned that you will be taken advantage of by some unscrupulous, attractive possibility.

Venturing into internet dating

With the usual channels no longer available, you head off albeit alone—but undaunted—to cure your loneliness and dip your toes into internet dating for seniors to find that perfect match on any one of hundreds of online dating sites. I will not detail how myopic many of these sites get, but the companies that engage in this kind of commerce really know how to empty your bank account by appealing to every aspect of your life and then some. Some forthright, others not so much, and finally others just downright shady.

So, you go through the process of signing up by telling the world your life story. What you are looking for and, if you are in it for a casual tryst, a look-and-see, or a serious attempt at forming a monogamous relationship.

Once you have posted your story and most importantly, your pictures, you are live and the fun of internet dating for seniors begins. People respond to you. You are amazed, elated and looking forward to that first coffee or cocktail chemistry check. It’s not a date: it’s a 30-minute audition to make sure you look like your pictures, you dress well and smell good, and you can put a series of sentences together. As this chemistry session comes to a close, the reward is you may become a candidate for a more expanded social encounter once known as a date.

Now people of our age do not “date.” We do not become boyfriends or girlfriends. We do not go steady. We become something nondescript because to succumb to those post-adolescent terms is ridiculous. We are, you know, together. We are introduced by others as his friend, her companion, or simply as, “this is Fred.”

How nice. The invisible man has arrived, and everyone wonders how long this one will last.

The reason why this falls flat is that this internet fix’em’up system is transactional, not relational. People scan the hundreds of profiles and get it down to 6-10 possibilities and then it is off to Starbucks for an outdoor chemistry check. Then reality bites and you say to yourself: is there anyone out there, or am I doomed to a life of solitude and loneliness forever? 

No, knucklehead, of course not. Understand that these dating sites are there to engage in commerce, not make beneficial introductions. The motive of internet dating for seniors is to keep you in place so that you will continue to subscribe to this secret society of cat and mouse. That is how they make money.

Yes, some people do find one another through this process and are quite happy engaging in it. Most, though, do not.

So, what is one to do? First off, understand that any new relationship, to succeed, must have some sort of relational intersection. Why? Because then you have something in common with this person. This inflection point is the first step in determining chemistry. Shared experiences lead to better and more meaningful conversations. And it is those conversations that lead you to want to know more about this person.

Suddenly, you relax. You stop talking incessantly. You ask a question. You listen, feel engaged, and find yourself more curious about this person. And – OMG – you feel chemistry!

Moving beyond internet dating

Now rewind. How can I get to this point? Do I abandon internet dating for seniors and look for other avenues? Well, no you do not abandon internet sites. They have you sign up for at least three months, so use that time wisely:

  • Scan the field, pick out your choices.
  • Ask them questions that will lead to that point of relational intersection.
  • When and only when you attain that, go for your masked coffee/cocktail processing and you will find that chemistry awaits.

But do not stop there. Find “Meet Ups” that appeal to you. Find support groups that speak to your individual condition. Find the chatroom where alumni from your former companies hang out. Attend small church socials and interactive school alumni webinars and anything else that you have an interest in that meets online for now.

Find that group that you relate to, and you will find your relational mate in attendance.  

For us Woodstock Warriors, it’s all a matter of networking. There is an incredible number of us out there all wondering where the rest of us are. We are right here. In plain sight. Ready for engagement. It is up to you to choose how and where to network. Just like it was in high school. Guys on one side of the room and girls on the other at the dances. Everyone filled with awkwardness and anticipation.

All it takes is that first step to find that person. Many will not have that intersection point you seek. But remember that humor attracts, and egocentricity repels. The one who learns to write with authenticity will win the day and the date or whatever we will call it.

It’s easy to give into loneliness and surrender to isolation, but the hunt is more fun if you bring the right attitude, questions and desire to find the right one. Just have fun with it!

Ready to retire and don’t know where to begin? Maybe you’ve tried forging your retirement path alone and are feeling lost in the woods and unsure how to get back on course to the retirement lifestyle you imagined. Retirement Lifestyle Coaching is here for you!

About Bob Foley

Bob Foley is your Retirement Lifestyle Coach and you can reach him by email at or simply by scheduling time on his calendar.

Bob FoleyBob Foley is on a mission to make sure your retirement lifestyle is designed just for you. After all, he knows how much retirement has changed in the past few decades. Because you’re not your parents, and your retirement won’t look like theirs.

You’re a dynamic and vibrant individual, and retirement isn’t about to change that!

Bob knows what it’s like to be a driven, career-minded professional who’s suddenly standing on the precipice of retirement, looking down on an unfamiliar landscape full of shadowy unknowns and big, looming question marks. » Meet Bob Foley