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How I Failed at Online Dating on the Very First Try


It took me only one try to become an expert on what not to do when online dating, and it was my own fault. Before signing up, I didn’t conduct a single piece of research, talk to anyone who had tried it, or even read the safety guidelines provided by the hosts.

Rather, one day I sat down at my computer, hopped on, pulled out a credit card and paid the 25 bucks that allowed me a month-long introduction to the world of online dating. 

Why so impulsive? Like most women saying goodbye to a relationship that was supposed to be forever, I was lonely.  My husband — actually my second husband — had moved out six months earlier, and I felt like a loser-times-two. At 48, I was terrified I would always be alone. 

“Dear Tdeer,” my first messenger writes. “I find your photos very attractive. You are so hot. Let me make you happy. Rob.”

According to his profile, Rob’s a divorced, professional dad looking for a long-term relationship. It‘s hard to see him in the picture because he’s standing behind a cubicle and the photo is a little out of focus, but he describes himself as average height, athletic, and toned. He’s looking for a woman with similar traits.   

Not realizing just how many contacts women tend to get, I grabbed on to messenger number one and set my sights on making this happen. After a few Match messages, we decide to swap phone numbers.

“How are you darling?” he texts the first morning. “Working hard?” a few hours later. “Can I bring you lunch — wink wink?” “Home yet?” “Time to talk?” 

“K.” “Ya.” “Not now,” I answer, trying to make this playful even though it’s becoming obnoxious.
 “Can we get married yet?” he asks on a first, unexpected voice phone call.

He’s coming on strong, but he does make me laugh, which feels so good because I’ve been so sad.  That afternoon, a large and expensive bouquet of fresh flowers is delivered to my office. I pick the card out of the plastic prongs.

“I couldn’t find an arrangement as beautiful as you. Forever yours, Rob.” 

That’s nice — and kind of strange. Then again, I’d told him I was a newspaper editor North of Boston and would be easy to find in a quick Google search.

We decide it’s time to meet and Friday night I’m on the stoop in front of my house waiting for Rob to pick me up. Mitchell, my 21-year-old son, asks what I’m doing.  When I answer, I get the look.  “You’ve never met him?”

“It’s online dating, you don’t meet first.”

“Aren’t you supposed to have coffee or something before you go to dinner?” 

“We talked on the phone.” 

“He’s picking you up here? At our house? Before you met him? What if he’s an axe murderer?” 

“It will be fine.”

Rob pulls up in a monster-sized truck from which it takes him great effort to exit. It becomes clear in a flash that he is extremely unhealthy, does not take care of himself, and the reason his photo was obscured was purposeful. I have committed my entire Friday night to a person who, in essence, thought it was OK to start a relationship based on a lie. 

“Good luck with that,” Mitch says. 

I feel incredibly manipulated. You can call me shallow, but I’m not, and anyone who has done some online dating understands — and you should, too, if you are about to take the dive. Let’s face it; the point of online dating is with the hope that at some point, the connection will lead to an in-person meeting. That experience shouldn’t feel like a moment of deception, but rather one full of excitement and hope.

I would have been justified if I’d called it a night, but I didn’t because I realized this was my fault, too, for ignoring all those little pieces homework I should have done at the outset. 

We share awkward conversation over dinner, I deflect a good-bye kiss on my way out of the big truck, and the next morning I contact him to say I don’t think we’re a good match. Interestingly, he takes down his profile shortly after. 

That crash course in online dating was humbling, but I did learn some rookie mistakes: If he’s hiding in a photo, he’s doing it on purpose; be suspicious if he’s coming on too strong; always have coffee before committing an evening; and never ever let him pick you at home on a first or even second meeting.

I am happy to report that I wasn’t so discouraged as to stop searching. Sometimes fumbling along and sometimes finding a lot of fun, I gathered experiences and made some lasting connections —  and oh, the stories to be told.

In fact, not so long afterward, I met my fiancé on Match, and after years of partnership, we’re getting married next month. 

Pretty romantic, eh? I wonder if they’d consider us for one of those cheesy commercials. 

This essay was written by Tracey Dee Rauh.

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