ReEntry into Online Dating

Over the past 6 months, I’ve taken a break from online dating. I have continued regular nights of dancing in Raleigh and added a new dance venue for Blues in Durham. I’ve gone to hear bands at a popular restaurant in Cary, shopped in three different grocery stores in my new town of Apex, and visited an area church fellowship several times. I’ve had family members contact me when they learned about men who were now widowers. To summarize, over the past months, I’ve “put myself out there” and gone about dating in the “old-fashioned” organic way. My therapist had told me that things would go more slowly than with online dating; he wasn’t kidding.

Photo by Uriel Mont on

I’ve talked with a couple of guys who are friends and dance partners. One, who’s been with a significant other for eleven years, made the comment about “dating the old-fashioned way” that he didn’t see men asking women out these days.

“I don’t know what’s the matter with them,” he said. “I asked my friend why he didn’t ask women out and he couldn’t give me a clear reason. I think he thinks he’d be ‘settling’ if he dated a woman who was less than fifteen years younger than himself.”

My immediate response was, “Why would a man in his seventies think that?” I’ve heard how men who are wealthy can attract women who are a lot younger– but the man my friend was speaking of is not wealthy.

The other guy I talked with told me he saw the same thing in the women at the dances; most of them only wanted to dance and weren’t interested in a relationship. In talking with many of the women I see at these venues, I think he’s right. By the time you’re in your mid-sixties, you’ve either had all the relationships you want or you don’t want anyone to interfere with your new-found freedom.

Looking back to when I ended my online dating subscriptions, I had needed a break from my two years on those sites. It had been an intense time of “studying the market” and while I’d gone on many meet-up dates, few resulted in satisfying dating relationships. I made a plan to reevaluate being on a site when I returned from Scotland last September. As it ended up, that decision was made for me when I purchased my townhouse and was busy with closing, finding contractors for repairs, then moving. By that time, it was the holiday season and things didn’t settle down until mid-January.

As another Valentine’s Day rolled around, I felt restless. I’d done what I could to date in the old-fashioned, organic way and it felt like I’d made little progress. Looking back at online dating, at least those men wanted to be involved in relationships. They’d put forth the effort by investing in a subscription and posting pictures and a profile. They were willing to “put themselves out there” and didn’t hold back because of having to learn the technical skills to navigate the site. They allowed themselves to deal with the anxiety of meeting women in “the new way.” They recognized their pool of possibilities were increased by getting rid of old barriers–of geography and our usual small circles of acquaintances.

With two years of experience across four sites, I felt much more confident about how to approach the process this time. I would only join one site and it would not be any of the same ones as before. This time, I chose eHarmony and answered the many questions on their Personality Profile. They would only allow 500 words on your personal statement–which forced me to nail down what was most important. There were more check boxes for interests, political and religious affiliations, etc and then there were questions you could choose to highlight your personality and life experiences. Once you completed your Personality Profile– you were given a Compatibility Score with the Matches that came up in your age category.

Besides choosing just one site, this time I felt it was better to let the process of getting to know someone unfold more naturally. From my experience of two years of online dating–it seemed that the initial messaging, phone conversations, and first meetings were forced and focused too quickly on our ultimate goal. Instead of just enjoying the moment and getting to know that person, we had ‘the talk’ about things that typically come up later in a relationship, after you’ve had time to get to know the person. Some of those meet-up dates were more like Q & A sessions or job interviews. We talked too quickly about what we were looking for, what we ultimately wanted, and asked questions about areas that may not be a match.

This time, I wanted to be in the present moment and just let the conversation flow. I would keep in mind areas of difference and wait until they naturally came up. Those first meetings with first impressions being way too important were not good for me. As a person who can make quick, sometimes harsh, judgements about things, that wasn’t the best way for me to get to know the guy. I had enough experience with handling my impatience, my anxiety that now, I could wait and let the relationship play out more naturally.

Before, there had been an intensity and as you read in my posts, it felt sort of like being on a production line of a factory– with those “toads” coming by at a regular clip.

I felt I had to make a quick judgement about whether they fit, or could potentially. In a post last July 24, I wrote about “non-negotiables” (see Non-Negotiables: Online Dating ). That had been a frequent conversation in both internet articles and among friends who were also dating. Now, I re-read that post and one of the reader comments that challenged my thinking. This is what he said:

“While I am in a stable relationship that started online almost 20 years ago, if we had had non-negotiable as you call them, we would never have gotten together, yet we became a successful couple. Things have certainly changed since then. It seems everyone now has things they refuse to overlook in a possible date/mate. I think this practice is not conducive to having something to learn from others, or having someone learn from you.”

“Almost all my relationships in life have been about learning how to get along with others, lessons that are important to life, and how to live it. Restricting your choices cannot help you grow as a person. Are we becoming so set in our ways that we want to live only with our clones, and not share life with those different from us?
This is going to create very boring lives, not to mention a very static way of life. It is good to find the similarities but we also need to celebrate the differences!” 

At first this reader’s words stung; was I becoming set in my ways? was my judgement too harsh– as I know I can be in other areas of my life?

Another reader challenged me about my statement that finding someone who loved to dance may also be a non-negotiable. She asked me couldn’t I compromise some on that. Now, I look back at all the dances I’ve attended, all the guys I’ve met, many single; those men didn’t necessarily feel more compatible just because they were dancers. I’ve seen couples who sometimes go together to dances, but in between, they’re secure with the more-dance-loving-partner going alone. As one dance friend says, “She knows who she’s going home to.”

One of my non-negotiables has been faith, and in the past, I was more specific on the sites about my Christian faith. While I noted that it’s “not conservative” and I added that I embraced “an expansive faith” including mystery and contemplative practices, I learned that all of that is interpreted based on a guy’s unique perspective, his faith experience. Over the past months, I’ve been reading and thinking deeply about faith over your lifetime, and especially informed by Richard Rohr’s Falling Upward: A Spirituality for the Two Halves of Life. I’ve considered my evolving faith and how it’s grown from my early experiences as a girl, through the challenges of setting up life as an adult, and been shaped by the struggles I’ve gone through. Now, I feel I can’t be so quick to rush to judgement by what someone writes on a website; I need to get to know them to understand what faith really means, how they’ve had their own unique experience of God.

I’m re-entering the online dating world at a different point in time, re-setting my way of interacting with potential partners. I want to be present, to not let quick, harsh judgements get in the way of forming a relationship that I’ve longed for. I’m trying to let go of my expectations and just let things happen ‘more organically’ to use a sometimes overworked expression but perhaps the right one for this situation.

You may not be in the same situation, but may be re-entering an area of your life–but from a new vantage point. Hopefully we’ll allow ourselves to use our own knowledge and lived-experience, and will trust our inner voice to guide us along our unique path.

Blessings on you as you make your way,


2 thoughts on “ReEntry into Online Dating

    • Hey Mary,
      You’re so kind and encouraging. I hope I never stop growing and learning–because we all need that to enjoy the richness of life.
      I believe you do the same thing, Friend!!
      Best to you,


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