YouTube Dating Yodas: No Thank You

I’d rather do it wrong all by myself

I haven’t followed many Medium writers on the topic of dating and apps, in part because this wasn’t ever a topic of interest for me, until…

Here we are. I’m 62, and became a widower 3 years ago after caregiving and helping my late wife Debi fight to regain her life quality following a devastating brain hemorrhage in 2019.

I left it a few months after Debi’s memorial service, then decided the loneliness and the sadness needed to leave me and be replaced with a sweet, loving relationship. After 17 years of blissful married life, I waded enthusiastically into the dating apps world. After a few comical and fun — and brief — adventures, I was about to give up. I had met a beautiful woman with whom we shared a strong attraction and trust, only to learn that the trauma of sexual assault two years prior was not yet put to rest, and we were not able to go any further.

Then I met a beautiful, recently divorced woman who manifested none of the seriousness or intensity I had just experienced, and instead was interested in fun, affection, trust, and good sex. We caught fire and very quickly fell in love. For my part at least, I was in love. We lasted almost two years. It was a fun loving and affectionate relationship, and I was extremely happy 24x7 from day one till the day she broke up with me. She cited a post-divorce identity crisis, and struggled to explain in more detail. Once I learn I’m not the one, I probably don’t need to understand the details of why. I was sad, but I picked up the pieces and tried to move on.

A few weeks later I created new profiles on a couple of dating apps, and began exchanging messages with women in my match list, then going on coffee or walk dates.

It took me three months to realize this wasn’t working for me at all and that I was doing it all wrong. Not blaming the apps or any of the women I met. I was being picky about physical appearance and shape, as well as cultural fit. I met several women I liked very much, and several other women who liked me a lot. And only one or two where we seemed to like each other equally, quite a lot. None of these potential love stories panned out.

Was I being too picky? Was I chasing too hard? Was my picker broken? I watched a lot of YouTube dating advice and it took me a couple of weeks to decide these people have some good points, but their advice is too clinical and dehumanizing for me. Yes, if one of us is too eager, too available, and trying too hard, the other will likely move away, step back, and continue their search. One dating coach advised we ask the question: “who’s the prize?” And if I am not the prize, then she is the prize, and why should she be at all interested in me?

Ok fine. But if we all adhered to dating yodas and their advice, we’d all be playing coy and hard to get, leaving it days before responding to a message, ignoring a clear signal of affection in order to avoid being too available. We’d all be playing cool and there would be no fire. Honestly, when I feel I like someone I’ve met a couple of times, I would rather be open and transparent about my attraction and affection for her. If she wants to play cool that’s OK, but eventually I may walk away believing she isn’t feeling anything for me. It’s a pity if she did like me and didn’t let me know.

There are 8 billion of us. Many people are lonely. It’s harder today to generate a connection with another person than ever before. We may wonder how many times did we walk away from someone wishing they liked us, not knowing they actually do, but didn’t find the chance or the courage to let us know. Even though we have friends, if we’re single we’re probably missing the intimacy and closeness we’d expect in a happy, loving relationship. We may find it hard to risk it all and let this person know we’re attracted to them.

My theory is: go for it. Let her know. Worst case, she can say sorry, she’s not feeling the chemistry. That won’t kill me, it may make me sad for a day, then I’ll be OK. I’m an introvert and shy, so this doesn’t come easy. But I prefer a leap of courage than the mystery of not knowing, and the tragedy of a missed opportunity to connect with someone I might fall in love with. I prefer the rejection.

Let’s be clear. I’m at a life stage where hookups and casual sex are less attractive. I’m hoping to meet someone I may fall in love with, delete the dating apps and enter into a new journey with her, hoping we last forever and co-create a great deal of happiness together.

The dating coaches may be right. I’ve been doing it wrong, causing myself unnecessary pain, and repeatedly coming back to square one, alone. My therapist suggests a break for a few months, working on me, being ‘enough’ as just me, playing more tennis, riding mountain bikes and spending more time with friends and family. When I return to dating, perhaps I’ll be more calm, more allowing of the universe, slower to fall helplessly for the next woman I meet. Let’s admit that a person’s loneliness isn’t a good reason to fall in love with them. A relationship based on need or a problem is already doomed. The best relationship odds are when both people can take it or leave it. Dating coaches can sound old fashioned too. Sadia Khan is beautiful and intelligent and interesting, but when you reflect on what she’s saying you feel she’s a medieval religious figure rather than a modern day psychologist. She preaches masculinity, financial security, decisiveness and male confidence. She seems to suggest a woman wants to be protected and have decisions made for her. I disagree. I’ve always been attracted to confident women who want an equal partner, not a dominant male. If all women were Sadia Khan, I’d probably be gay.

Should I settle for someone I don’t feel on fire for? The problem with this idea is that each time I ended an early stage dating story, I had honestly asked myself whether I’d be excited to be in a long term relationship with this woman, and came up with a negative. Getting on a plane together for a long flight to some new adventure, resting on each other in our coach class seats, sharing a sweater to warm our legs, looking at phone photos together, playing Wordle. If I don’t see her in the dream, then I’d rather stay single and keep searching. Or take a long break.

I invite your comments. It’s clear I know very little beyond how I feel.

PS: I wrote this from the perspective of a 62 y/o straight male but I hope it’s inclusive and pertinent to all.