My Second Online Dating Experience

A little over a year ago, I decided I was ready to try the swipeathon dating apps to see what all the fuss was about.  A couple of days later, I matched with a very pretty woman whose profile simply said “Reverend.”  It turned out that she, like me, was a former minister, and that we had several friends in common from seminary and ministry circles.  After a few minutes of really fun banter, we decided to meet the next evening.

When she walked into the coffee shop the next evening and spoke my name, I felt a warm glow descend over me like a comfortable blanket, and the look in her eyes felt like home.  We talked until closing time, sharing story after story of our respective journeys and opening up to each other about our struggles and challenges.  We laid our cards on the table, from our respective divorces to our various mental and emotional health challenges.  It felt safe. It felt natural. It felt real.  After closing, we walked across the street to a bar to get something to eat, and we continued to talk until the place closed.  We agreed to see each other again, and the next day enjoyed lunch together when she happened to be downtown.  A third very fun date took place a few days later, and then spent a mutually agreed upon week apart, since she had a friend who was going to be visiting from out of town.

Over the course of that next week, a few things happened that I hadn’t anticipated.  Some of my insecurity from previous relationships seeped in, and I started to wonder if she had forgotten about me.  When we exchanged text messages, they were typically short, and she once said “thanks so much, friend” to me.  While I was certainly rushing to assume anything beyond an affectionate friendship after three dates, I could tell she was pushing me away.

And then my mom died.

I let the woman in question know about what had happened, and received back a short message telling me that she would be willing to meet with me to talk the following week, but that I needed, in the meantime, to take care of myself and my family.  I was, naturally, preoccupied for the following week, but found her brevity and lack of engagement confusing.

When we finally met, she informed me that she had actually had no business being on dating sites given the state of her life at that time.  She admitted that she had been seeing someone who had disappointed her, and that she hadn’t expected to meet anyone with any depth of character or with whom she could make any actual connection.  “What we had was real,” she said, “but I’m just not in a place where I can really experience that, and I don’t see it happening any time soon.”  She offered to be friends, but I gave her a self-righteous and cocky speech about how I had no interest in being friends, that she was making a mistake, that she would miss me, and that she would simply have to wonder what we could have had.  I kissed her goodbye, and walked away.

While this felt like the most triumphant version of the way a breakup movie should end, it wasn’t.  We went our separate ways, experiencing whatever triumphs and defeats our respective lives held.  A number of months later, when I was working through a few things in my own journey, I sent her a message apologizing for the way we parted ways, and told her I hoped she was doing okay.  She politely thanked me and wished me well.

It used to be that when people parted ways, they parted for good.  In the days before social media, we said our goodbyes and resolved ourselves to permanently wonder about the other person.  There was no way to check on anyone once you’d walked away from each other.  For all we’ve gained with the changes in technology and time, and despite the obvious advantages of being able to maintain friendship over miles and space, we have also undeniably lost a few important skills, such as how to say goodbye with grace and dignity, and how to move forward with life once someone has left it.  No moment seems final anymore, and perhaps that’s why it’s so much harder to accept when a moment really is final.  At some point, you will say goodbye to someone, and that really will be the last time.  The hardest thing to accept, sometimes, is that there also might never be a way to fix, heal, or improve what happened.  Sometimes we heal and help each other heal.  Sometimes we wait to see if time can heal what effort can’t.  And sometimes we must make our way wounded, hopefully not harming anyone else in the future.

I wish I had handled things better when I had the opportunity to.  While we had some differences that might have become problematic or at least challenging later, the connection we shared, even for a short time, reminded me of the best ways that people can be together, and gave me a hopeful glimpse into the kind of life, relationship, and intimacy that I long to have again someday.  I don’t ever expect to see her again in person, but I hope that despite everything that happened in that short vignette, we can both be better versions of ourselves as we live the lives we each have.