Dating : Dating While Baby-Boomer, Part 1: Reflections of a Reluctant Flirter

It is hard to meet someone in an organic way, let alone be constricted by digital rules. What are you searching for? Does height matter? Education? Or is it all just about looks?

Uncoupled for years, when I became an empty-nester my handy excuse for not dating had left home and was now living in his dorm room, several states away. My friends implored me to start online dating. The marrieds wanted someone to double-date with, and the singles wanted someone to swap stories with.

I finally placed my excuses on the table and picked up my laptop.

In a savage attempt to plunge into online dating, I signed up for six months. My thought process was my experiment would elicit a multitude of dates and by the end, I would have found my guy, or a guy.

My dating descent was less like a dip in the pool and more like being swallowed by quicksand.

This wasn’t my first foray into online dating; every few years I sign up, go on one (usually none) date, and then delete the app. I give it the respect I give vitamin B; I know it is something I’m supposed to care about, but don’t.

I asked friends to brainstorm ideas for desirable proclivities and personality traits, and these bullet points were crafted into the profile that I presented to available males in my age range.

Before I go any further, I want to acknowledge how difficult it is to meet new people that you would want to date. I occasionally meet someone the old-fashioned, organic way, but my job and my inordinate amount of single friends don’t bode well for meeting someone. While I would complain that it is hard to meet someone my age, my millennial friends tell me it is just as difficult for them, for different reasons.

We have all heard that this culture of swiping right causes daters to think there is always someone better waiting after the next swipe. I don’t doubt that this is true, but I’d be lying if I said I didn’t want to meet one guy the first week and then be done.

I went on three dates my first week. Each guy was nice, and each one reacted amicably after I decided I didn’t want to see him again. After the first measure of dates had occurred, I knew a little more about what I was looking for, so I adjusted my search filters. Pay attention to your own tipping point on what you do and do not want.

The first date was an interesting guy who I could have been friends with (read between the lines, no chemistry). While a nice guy, I later realized all his pictures were of him from a distance, wearing sunglasses.

Lesson learned: Be kind but honest when turning someone down. If a guy asks me why I don’t want to see him again, I say “I did not feel we were an ideal match, and I wish you well in your search.” I really try not to ghost someone (do unto others) unless absolutely necessary. A little honor goes a long way.

The second date was younger than me, cute, and upbeat. I liked his energy, but we ran out of things to talk about after a minute. He was more interested in my Burberry coat and the type of car I drove than what I had to say. After the date, there was a spate of texting back and forth, but I didn’t see it going anywhere, and I was looking for more than just fun. I didn’t go on a second date with him and I have no doubt he moved on to someone more suitable.

Lesson learned: If you are unsure that you want to go out with someone again, you probably don’t. Let them know and then move on.

The third date’s profile had potential — worldly, an interesting profession, and Canadian. Upon meeting him, I was enjoying our conversation until about 15 minutes into the date when he confessed that he had never gotten married because “his mother was his soul mate, and he was hers.” I couldn’t really move forward after that. A nice guy, but not for me.

Lesson learned: You have to get out there and go on dates if for no other reason than to provide your friends with good stories.

After the first few weeks, I took some time off to be mindful of the process, and to reset. I continued to monitor the app, liking a few people here and there, occasionally writing a message or two. I had a few men reach out to me during this time, and I would like to say that I wrote all of them back, but if I was not interested then I did not engage. My southern mother would have been disappointed in my manners, but my millennial friends told me not to bother.

For all the guys that I didn’t like, there were plenty that I liked that didn’t like me. You can’t have too much skin in the game; it is just the way of online dating.

After five months, I had gone on eight dates. I became more discerning as time went on. Toward the end of my subscription I turned off the app because I was traveling a lot, so I became more focused on that and less focused on meeting someone. Was it too much work, am I too picky, or just not the right time in my life? I may try online dating again, but maybe online dating just isn’t for me? I always have the choice of staying blissfully single.

After years of living without a partner and knowing I can take care of myself, I’ve earned the right to know what I want.

Online dating is its own Pandora’s box. Regardless, I’m content with my choices. While I may have not found a match, I still haven’t given up hope.

I may be a reluctant flirter, but I’m still a hopeful romantic.