Online dating woes and triumphs

Dating Is the Worst editor Jill Holbrook. (Courtesy Jill Holbrook)

WASHINGTON — After four years and roughly 50 dates, Jill Holbrook knows how to recognize a good catch.

There was the guy she fell in love with but who moved away to Turkey early into their relationship.

And there was the guy she dated for five months but then disappeared without saying a word.

And then there was the guy “who didn’t understand sarcasm,” didn’t listen to music, didn’t like sports and showed her countless cat photos after Holbrook told him she didn’t like felines.

Many of these stories and more can be found on her blog Dating Is the Worst, which the 27-year-old D.C. resident started at the behest of her friends.

Though some of her online dating experiences were admittedly unsuccessful, most were funny and made for great stories after the fact, she says. Holbrook quickly realized she wasn’t alone in her dating woes, so she opened up her blog to contributors.

To emphasize the humorous side of online dating, Holbrook likes to add pop culture references when applicable. Her most recent date, for instance, got the Harry Potter treatment because of his resemblance to the Weasleys. And “Overzealous Monday Guy” gets a sly “Titanic” reference when things got steamy in his car.

Having a sense of humor and keeping an open mind is what online dating is all about, she says.

“There are a lot of really interesting people in this city,” she says. “I’ve had a lot of fun doing it. It’s hard, but it’s fun.”

While Holbrook is able to keep a positive attitude about the dating scene, not everyone has good memories.

Consider Mike LaRosa, whose date turned out to be an identity thief:

“Basically I met a guy online. Started dating him and a few months later found out that he had stolen my identity, opened up credit cards in my name, had 12 prior convictions in Maryland, had also been doing the same thing to two other guys,” LaRosa writes in an email.

LaRosa wasn’t this person’s only victim, he says. The identity thief had also allegedly targeted his former employer.

Ryan Holeywell says he got lucky meeting his current girlfriend after going on 40 dates with other women:

He has “been stood up, gone out with people who didn’t look like their photo, people who just wouldn’t talk, people who were dumb as rocks,” he writes in an email.

“OkCupid honestly caused lots of stress and disappointment for me… But I have it to thank for meeting the love of my life.”

Do you have an online dating disaster story or an especially inspiring one? Comment here or call our Talkback line at 1-877-222-1035 to share your experience.


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