How Online Dating After 60 Led Me To Find True Love Twice

You may wonder how I got so lucky when it seems so many people have a hard time finding true love at 60 and beyond. Maybe you aren’t having success either.

I was fortunate. I had two love relationships (one is still going strong) starting in or near my 60’s.

No doubt part of it was luck. Maybe luck is always involved when you’re looking to find your soulmate.

But also, I went into the dating experience with a game plan that I put together based on my other career as a job search strategist for executives.

I treated my dating life like it was a job search.

Here’s my story . . .

How Online Dating at 60 Led Me To Find True Love Twice

In my 20’s, when I met my future husband, I wish I had known how and why I was destined to marry this person who was wrong for me.

Coming from a narcissistic family was one factor.

With this kind of upbringing, you go forward in your life driven by the modeling you observed by your parents and siblings.

My understanding of what my partner should be was based on my emotionally distant, bullying father.

Naturally, I married a narcissistic man. I chose a man who was like my father, because he was my role model for a mate.

Even though I vowed at the time never to marry someone like my father, my relationship with him was mirrored in all my relationships with men, up to and including my husband.

Although I didn’t understand it at the time, there was comfort in being with men who were like my father.

Why some of us date (and marry) the wrong people and never find true love

Philosopher and author Alain de Botton explains this phenomenon:

“Though we believe ourselves to be seeking happiness in marriage, it isn’t that simple. What we really seek is familiarity — which may well complicate any plans we might have had for happiness. We are looking to recreate, within our adult relationships, the feelings we knew so well in childhood. The love most of us will have tasted early on was often confused with other, more destructive dynamics: feelings of wanting to help an adult who was out of control, of being deprived of a parent’s warmth or scared of his anger, of not feeling secure enough to communicate our wishes.
How logical, then, that we should as grown-ups find ourselves rejecting certain candidates for marriage not because they are wrong but because they are too right — too balanced, mature, understanding and reliable — given that in our hearts, such rightness feels foreign. We marry the wrong people because we don’t associate being loved with feeling happy.”

That is powerful stuff, isn’t it!

He goes on to suggest who IS the right kind of person for us:

“The person who is best suited to us is not the person who shares our every taste (he or she doesn’t exist), but the person who can negotiate differences in taste intelligently — the person who is good at disagreement. Rather than some notional idea of perfect complementarity, it is the capacity to tolerate differences with generosity that is the true marker of the “not overly wrong” person. Compatibility is an achievement of love; it must not be its precondition.”

At 58, I had been divorced, living alone for about 6 years and only dabbling with dating.

Being alone for several years was a very good thing for me. I wasn’t lonely and I mostly enjoyed it.

I worked on sorting out what truly went wrong in my marriage and what part I had played.

And I got sober. That was a huge step. My mind cleared and all the energy I had put into thoughts and actions revolving around alcohol was freed up to put into figuring things out about myself.

When I decided I wanted a serious relationship, I first tried traditional dating methods for a few years, but with zero success.

Then, although I was hesitant and even sort of afraid to use online dating sites, I did so anyway.

Relying on my years of experience in the careers industry, I treated my dating life like it was a job search, because they’re so similar.

How Dating Is Like Job Search

Here are the steps for job search vs. dating, side by side:

1. Personal branding / Knowing who you are

Defining and understanding your personal brand (or who you are) will help differentiate you from others competing against you, in job search or in dating.

2. Targeting

This is the same for both job search and dating. You need to know who your ideal employer is for job search, and who your ideal partner is for dating.

3. Research

Again, the same in both instances. For job search, learn about your target employers so you can present yourself as the right hiring choice.

For dating, read about dating over 60 and talk to people you know, to learn more about what people who would be an ideal partner are like and what their needs are.

4. Writing and talking about yourself / Communicating who you are

In job search, use the first 3 steps above to help you write a resume and other job search materials, designed to resonate with the employers you’re targeting.

For dating, you need to be able to tell various people, including dates, in a clear and succinct way, what kind of person you are and who you’re looking for. And you need to be able to write profiles for the online dating sites you’ll use in a way that will resonate with the people you want to date.

5. Networking

In job search, you need to reach out to everyone you know and tell them what you’re looking for. And you need to be active online, on social media, positioning yourself and the value you offer in front of people looking for candidates like you.

For dating, tell everyone you know (if you’re comfortable with them knowing) that you’re actively looking, and what you’re looking for. Ask them if they know anyone who fits the bill. Dating sites are social networks too, just like LinkedIn and Twitter. Reach out to people on the dating sites who seem like a good fit for you.

6. Interviewing / Going on dates

This is a more obvious analogy. For job interviews, you do some prep work so you’ll put your best foot forward in presenting yourself. The employer assesses you while you assess them.

Same thing for dating. Prep for dates by having a few questions to ask them, based on what you already discussed in emails or by phone. You’ll assess your date and they’ll assess you.

The more dates you go on, the better you’ll do each time, and the more comfortable you’ll be on first dates.

7. Accepting a job / Making a relationship commitment

After looking over all the details, you make a decision about whether to accept a job offer.

After you’ve dated someone long enough to know whether they’re right for you, you decide whether you will make a long term commitment to them.

Someone is right for you if they meet most of your needs, based on whatever criteria you set out when you did the initial steps noted above. Don’t expect perfection. After all, you’re not perfect either.

I Still Faltered, Despite Using My Dating Game Plan

Unfortunately, when I first started online dating, part of me was still attracted to men who weren’t right for me.

I had several casual dates with a man who was emotionally unavailable and constantly tested boundaries with me.
I had a short but intense one month relationship with a man whose wife had died 3 months earlier and he was still heavily grieving.

Clearly, I needed to work on why I was still choosing the wrong men, and I did.

I decided that, going forward, I would go against type and choose a man who didn’t have that swaggering, emotionally closed and overly sarcastic personality.

I would look for men who were quieter, listened better and smiled more.

Shortly after that, I met Sam.

He proved to be just what he initially appeared to be – kind and gentle, fun to be with, loving and respectful.

Sadly, three years in, he died suddenly.

At some point in my grief over the months that followed, I knew that I would once again try to find true love.

Although I was happy living alone those years before I met Sam, I wanted to experience a long-lasting loving relationship.

I SO Much Wanted To Find True Love

Like so many of us dating over 60, I didn’t want to grow old alone.

Being with Sam helped me see what a (mostly) good relationship really looked and felt like. I was so grateful for those 3 years with him.

Online dating had worked so well for me with Sam and, now that I had some experience with it, I was that much better prepared to use it well.

I felt I now knew what kind of man was right for me and how to find him.

But I knew enough not to jump into dating again too soon after he died.

At about 3 months, I felt ready and started dating.

I was wrong. I wasn’t emotionally ready. I felt compelled to immediately bring up Sam on the few dates I went on, which I’m sure was off-putting for my dates.

So I backed off dating for another few months.

Then a long, sometimes fun and sometimes agonizing, year and a half of online dating ensued.

This time I went into it with much more clarity around who was right for me.

I made it through lots of first dates

I had plenty of first-and-only dates:

One of the worst dates I ever had was memorable for how truly nasty he was to me and for the fact that I foolishly sat through an entire dinner with him.
Another bad first date was memorable for how I risked saying “this isn’t going well, is it?. I managed to turn things around so we both relaxed and it became a very pleasant experience.
I came to see that every date was worthwhile because I always learned something about myself and what kind of men were right for me.

Even though I didn’t have that many awful experiences, after 1-1/2 years of dating, I was burned out and was about to take a month or so break.

And then I found Cosmo

As was my daily routine, I scoured the dating sites for any new guys, and there was Cosmo.

There was nothing in his profile that was offensive or negative and a few things that were intriguing. Plus he was very nice looking, and had a warm, genuine smile.

I reached out to him immediately. One strategy I had learned in all that previous online dating was to act fast when you saw someone new on the sites.

He got back to me quickly. He told me later on that he was also planning to take a break from dating but my email to him and my profile intrigued him.

We exchanged several emails, then spoke by phone several times.

There was definitely a spark, so we planned to meet for coffee.

We had a knockout first date

That first date was the best one I ever had. We met at Panera for coffee and lingered for 4 hours, talking about all kinds of things. He was truly interested in what I had to say and vice versa.

I was buzzing with excitement as I drove home after the date. I happened to leave the parking lot right behind him.

After a few minutes still driving behind him, I realized he must live somewhere near me.

Indeed, he led me all the way to my house and slightly beyond.

Turned out he lived across the street from me, and had lived there for 7 years!

We had never met and probably never would have, if not for online dating.

After the second date (for coffee again) I was sure he was “the one”, based on my experience with other dates. He later told me he felt the same on the second date.

Things fell in place quickly and easily, and we saw each other frequently. I think that’s one of the keys: Everything was easy. Not stressful, but exciting.

About 9 months into the relationship, he moved in with me.

We’ve been very fortunate to have an abiding, loving relationship for 8 years now.

My Advice To Find True Love After 60

So, based on my own experience finding true love twice, here are my recommendations to anyone dating over 60 and looking for that special someone:

Look at your past relationships

Think long and hard about what went wrong.
What was working, what wasn’t?
If you had a bad break-up, how did you contribute to the downfall of the relationship?