What 5 Years of Online Dating Did to Me

My Evolution from Newbie to Veteran

Bonnie Barton
7 min readFeb 16, 2019


She may need a touch-up and a brush, but she’s still got a hint of a smile/Credit: Mean Shadows via unsplash.com

I began online dating a little over five years ago. I hadn’t dated since the prior century, my self-confidence was low, and I had been warned about how bad online dating was.

I was scared and nervous, but threw myself into the process (with my therapist and dear friends nearby)!

The reality is that you can research, self-reflect, and prepare only so much. Eventually you have to jump in.

And one can only truly appreciate the murkiness and challenges of the online dating waters once he or she’s actually immersed.

I recently realized how differently I approach dating now vs. then.

It’s been an evolution over the past five years.

I’m a lot savvier and more confident these days.

But I’m also wary and jaded by the process.

Miraculously I’m not bitter, though!

My heart’s been beaten up in the process but I still believe in love!

Online Dating: Newbie vs. Veteran

Communication Prior to First Date

Newbie Bonnie

In those early days, I enjoyed getting to know guys before I met them.

I texted.

I initiated a fair amount.

I followed up.

I asked to talk on the phone.

It made the first date less awkward for me and allowed me to weed out the occasional mismatch.

It also meant that I put in a lot more effort on each guy and in the process in general.

I was still learning about myself, guys in my age bracket, and what dating looked like post-divorce.

At that time, I didn’t mind putting in the extra effort.

Part of that was for my own growth and information.

But, yes, a lot of that effort was for the benefit of these guys — guys who were strangers to me.

I assumed that I would most likely meet the guy for the first date, so I was motivated from that perspective as well.



Bonnie Barton

Queen of mixtapes. Lover of music, travel, and fashion. Authentic sharer of life lessons and dating foibles.