When yet another romantic relationship came “burning down in a spectacular fashion,” Amy Webb sought the advice of her friends and family, including her grandmother. “She said, ‘Stop being so picky. True love will find you when you least expect it,’” Webb recalls in her TED Talk.

This advice struck Webb, who works with data for a living, as preposterous.  She had calculated that, in the entire city of Philadelphia, only 35 men had all the qualities she was look for and was still single. “I can take my grandmother’s advice and sort of ‘least expect’ my way into maybe bumping into the one [of them] — or I can try online dating,” she says.

Online dating is, in fact, the second most popular way couples meet in today’s technologically-mediated world. But when Webb began the journey, she found it much more fraught than she’d anticipated. “I like the idea of online dating because it’s predicated on algorithms,” she says. “These algorithms had a sea full of men that wanted to take me out on lots of dates—what turned out to be truly awful dates.”

At this point, Webb decided to get really systematic, and to find out how to make online dating work for her. She made a list of 72 items that she was looking for in a man, then ranked them by priority. She created a fake male profile so she could decode popular women’s strategies and then reverse-engineer her own profile. When she applied her rigorous ratings system to her plethora of possible matches, she wound up with just a single person who met all her criteria.

They went on what turned out to be a good date. In fact, a very good one. To see just how good, watch the talk.

Ahhhh, online love. Read on for some more delightful (and wonderfully nerdy) online dating stories we found, well, online.

1. “Geeklover,” who posts her tale on The-Gaggle.com, joined the dating site Geek2Geek (yup: a dating site for geeks) by force. In other words, her friends created a profile for her as a joke. But after she clicked around the site a bit, she thought that maybe it wasn’t such a bad place for her, a self-described history nerd, to find love. She spiffed up her profile and went on a good date with a major video game enthusiast. But it took a chance encounter between them in real life — on the New York subway to be exact — for both of them to realize that they actually had real potential.
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2. An adorable OKCupid Success Story: the first time Andrea and Michael IMed through the site, they talked for 12 hours. Despite the fact that they lived 1330 miles apart, they began talking daily, for months, before finally meeting. Less than a year later, they got engaged and are currently planning their wedding. Andrea’s best advice to anyone else hoping for love on the site: “Answer as many questions as you can … our match % was 97!”
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3. Willard Foxton’s date tried to “sexily nibble” him over dessert. Instead, she bit him; he bled and became ill. “So yeah, an infected human-bite wound. Beat that for a dating story,” he writes in The Independent. But Foxton persevered, and in fact decided to blog about his dates, committing to 28 in total, with 14 from mainstream sites and 14 from more specific ones “such as BikerDating, Sea Captain dating or Godmother (which matches royals with commoners).” Spoiler alert: as with the stories above, it also worked.
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4. Earlier this year, after it was discovered that Notre Dame linebacker Mant T’eo’s deceased online girlfriend had never existed, CNN asked readers to share their stories of online dating hoaxes. Barbara Hassan began online dating through Match.com in 2010 and started corresponding with an “architect/construction manager who built and designed a building in Nigeria for orphans.” She, of course, realized this wasn’t true when he asked her to pay for a $2700 plane ticket to the United States. A year later, she felt bold enough to try online dating again — this time with great success. How did she bond with her now husband? They both shared their tales of being scammed by online paramours.
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5. When Gemma discovered her partner was cheating on her with women he met using the website Plenty of Fish, Gemma ended the relationship — and joined POF herself. Here, she gives the nuts and bolts of her unusual success story.

All this said, not everyone is thrilled with the sweet nerds they meet online. Take, for example, writer Alyssa Bereznak who wrote the Gizmodo essay, “My Brief OKCupid Affair with a World Champion Magic: The Gathering Player.” After two dates, she broke things off with him, concluding, “Maybe I’m shallow for not being able to see past Jon’s world title. I’ll own that. But there’s a larger point here: that judging people on shallow stuff is human nature; one person’s Magic is another person’s fingernail biting.”

What has your experience been with online dating? Do you prefer to leave love up to serendipity, or do you relish the opportunity for data to guide you on the way?

This post originally ran in October of 2013. It was updated for Valentine’s Day 2015.