Misadventures in Online Dating

Brooke Dilling | @brookefrances

When my marriage ended in 2014, I found myself turning 40 and a single mom of 2 young boys. Yaaaaay. The thought of reentering the dating world after 10 years sounded horrifying. And to be honest, it hasn’t been pretty.

It took a bit of time post-divorce to feel ready to “put myself out there.” For one, I wasn’t sure I could really commit much time to dating. My sons were and still are with me 90% of the time. Dating seemed like a daunting process I simply didn’t have time to address.

In part for this reason, when I decided to stick my toes back into the dating pool, I started with . . . Tinder. I know. I know. But it’s FREE. And low commitment. I now know why.

I swiped right. I interacted with several guys. They seemed fun and interesting and good looking. Over the course of a few weeks, I agreed to meet a few for coffee or an after-work cocktail. And every single one of them was nothing like their evidently 10-years-and-20-pounds-ago profile pics suggested. 

Disappointing for sure. And a waste of my limited free time. But the end to my adventure with Tinder was the appearance of a friend’s husband in my Tinder feed. Aaaaaand Done. This site certainly isn’t for people who are serious about dating. (For hilarious pictorial renderings of Tinder interactions, check out badass broad, Audrey Jones' Tinder Diaries.)  

After a few months of getting over my initial “liar, liar, pants-on-fire” Tinder-shock, I moved on to something more “serious.” Something requiring more time and financial resources. My reasoning: maybe if people have to pay money, they are more serious about dating. I signed up for a 3-month membership to Match.com and set up my profile.

For those of you who may not be familiar with the marvels of online dating platforms, Match.com necessitates you fill out your profile, post photos, and indicate your personal interests as well as what you are looking for in a potential partner. I selected an appropriate age range--mid 30’s to mid 40’s--and got ready to meet someone interesting. It wasn’t long before I was getting blown up with messages from men. All in their late 50’s and into their 60’s. Men closer in age to my father than they were to me. Where were the men in my age range? They seemed to be interacting with women in their 20s. Was this a new dating phenomenon? Was the prospect of dating someone in your decade age bracket passé? After three months of Match-dot-com’ing, I called it quits.

I’ve heard about the newer online dating apps and platforms like Bumble, PlentyOfFish, and Zoosk, but decided my dating plan is “divine intervention.” If the universe wants me to meet “Mr. Wonderful,” the universe is going to have to drop him from the sky right in front of me. I’m done wasting my time, energy and money searching for him online.


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