Online Dating Tips

In the Rearview | the Urban Dater


Our text exchange on Hinge was pretty amazing. She was witty, funny, engaging, and so excited to meet, just as much as I was. I couldn’t wait for our date. And the date was pretty darn good, honestly.

She messaged me:

Hey, I haven’t heard from you. I guess you’re not interested? Good luck to you then.

I hadn’t reached out to her right away, that’s true. I wanted time to reflect on the date. Again, I had so much fun, our conversation flowed. However, when it came to what we thought about relationships my date got a bit flustered. I’m not even sure I want to date someone, to help them level themselves up or whatever, I’m tired of that. She said that in response to me sharing what I wanted out of a relationship. I said I wanted a relationship where we could be weird together, lean on one another, and do life’s good and bad parts together.

The notion of the good and bad parts really sparked some fears within my date. You see, she had a chaotic/traumatic upbringing herself, similar to my own upbringing. She went on to share stories about how she cares for her father, who has Alzheimer’s. Some of the stories were kind and sweet, some were heartbreaking. Some red flags began to surface. It was clear that she has very real fears when it comes to being able to protect herself and make a sustainable life for herself, that’s a real thing. I, too, share some of those fears.

When it came to her past relationships, I could see the patterns clear as day as she explained her past relationships (she brought up the topic to begin with) and how they came apart. She would get close to someone and then she found issues with her partners, maybe one partner was a bit vain and wanted help filming content for his Instagram feed, another one she felt relied on her too much and needed hand-holding, she said. Yet another one has begun to inconvenience her time with her friends, wanting to be included in her time with them—it wasn’t something she wanted to entertain. She wanted a clear division of your stuff and my stuff. It was a familiar pattern, one that I’ve been talking about in therapy for over a year now.

Our discussion carried on and even attachment theory had come up and I asked my date if she’d read up on the subject. No, I’ve heard of it but I have too much other stuff going on to really dive deeply into it, she said. She dismissed the topic in much the same way I had when it was brought to me. I told her it’s worth your time to look into it. I’m not a therapist and far be it for me to tell anyone what to do with their personal mental health stuff but what I was hearing from my date resonated with me pretty closely.

As the date drew on, as our talk of relationships deepened, it became clear that my date had engaged in some level of self-sabotage of her relationships and also that she had a deep affection for a male friend of hers who she pushes away. My date then asked why are you single? She cut me off and said it’s like why even bother, right? I explained the work I’ve done on this front. Well, if that’s recent then maybe you should give it a rest. I was taken aback but I chose not to take it personally. I told my date that growth and learning is lifelong process and that I’m not embarrassed by or discouraged by the work I’ve done and still do.

We had a nice hug but no kiss to end our date and honestly I was deflated, not because there was no kiss but because I had been excited about something that didn’t pan out as I’d hoped it would.

So, I sat there looking at my phone and stared at the reply from my date and I finally replied

Hey there. I’m sorry I didn’t reply sooner. I took some time to think about our date and it seems like what we want and how we view relationships are quite different and honestly I’m a little weary to proceed. I’d like to go out again but I think we’d be wasting each other’s time.

My date replied I agree with you there. Best of luck to you!

It was an unexpected juxtaposition I was witnessing. In some ways, I could see my past self hard at work inside of my date, she has fears, and experiences, that are valid, and traumas that still require mending, from what I observed. If nothing else, I know I’m headed in the right direction and this was a good reminder of that.


Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he’ll be sure to write.



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