On one date, the guy ordered the most expensive menu items at a restaurant then left her with the bill, Webb describes in a TED talk.
One of the problems Webb found with online dating is that she and her matches weren't filling out their profiles honestly.
Instead, Webb said, she'd simply copy and pasted lines from her resume into the blanks beneath each questions. Where the site had asked her to describe herself, for example, she wrote things like "award-winning journalist" and "future thinker."
These answers weren't matching her up with the types of people she wanted to meet because they didn't accurately describe her personality. Instead, they described how she'd want someone interviewing her for a job to see her.
Unfortunately, the answer to her dating conundrum wasn't simply being more honest and taking time to actually answer the questions, she found out.
Why? Because even if she decided to be completely frank in her answers, her matches probably wouldn't be.
"Very few of us have the ability to be totally and brutally honest with ourselves," she says in the TED talk.
As a result, we keep getting matched up with people who don't fit our personalities at all.
Research supports her idea. In a recent study of undergrads, 60% of participants lied at least once during a 10-minute chat with a stranger. Another study estimated that the average person lies during one in five of his or her daily interactions.
With this is mind, here are the steps Webb took to get the matches she wanted:
First, she laid out all the things she actually desired in someone else: A sense of humor, an easy-going personality, etc. Then, she started looking at the profiles of the people she wanted to match with, and looked at the women that these guys had gotten matched with instead of her.
She had wanted to seem open, light-hearted, and friendly, but instead she came across as distant. "It's about being more approachable," she said during the talk.
Using her findings, Webb made over her profile, including more honest, open language - and photos where she could actually be seen.
A few weeks later, Webb became, quite literally, the most popular woman online, she says.
And thanks to all her hacking, she found the perfect match. They're now married with a kid, in case you were wondering.
Watch Webb's full TED talk: