Weaving a Webb of love: One entrepreneur’s strategic approach to online dating

Martha Stewart made headlines when she announced on national TV that she was joining an online dating site. Amy Webb could give her a few pointers about looking for love.

A storyteller, serial entrepreneur and digital strategist, Webb is the bestselling author of Data, A Love Story: How I Gamed Online Dating to Meet My Match.

“Dating for a partner is like looking for a job. It is a full-time commitment,” says Webb.

Webb started telling her story about creating a system for finding a relationship on South by Southwest panels, a conference that highlights emerging technologies, big thinkers, original music and independent films. The session became so popular that she was encouraged to write about her strategic search for a partner.

You can trust chance to help you find people to date, but not necessarily for finding a life-partner, says Webb.

And the serial entrepreneur, who was working 90 hours a week, didn’t have time to wait on chance.

Webb knew from experience that trusting serendipity to find an ideal partner was risky and frustrating. After a failed relationship that lasted longer than it should have, and lukewarm success with blind dates and online dating sites, Webb decided she needed to change tactics.

She approached the search for her husband the same way she approached other important decisions: She made a 72-point list, created a scoring algorithm and weighed her options.

“You need to figure out a way to evaluate what you want” says Webb. In her book she encourages readers to build their own plan.

Webb’s carefully analysed wish list worked for her – she married the first man she dated through her system. Now she’s balancing her career, relationship and family.

Webb talks honestly in her book about the challenge to manage a full-time (albeit fulfilling) career as the CEO of her own company while trying to date.

Today Webb still wrestles with finding a balance between her career and her relationship.

“It’s a constant struggle. It’s an exhilarating struggle. It’s a problem,” she says of her hectic work weeks. However, Webb is quick to note that one of the points on her partner list was “to understand how important [her] career was and be willing to support [her] in it.” Webb says that it was crucial that she didn’t need to rearrange her life to fit in a partner; rather she needed to find someone who balanced out her life.

Today Webb receives a steady flow of emails from readers who have read the book and tried the “Webb method.” While not scientific, it has had a fairly high success rate for her readers.

Perhaps Martha Stewart should take note.

Hear more from Webb at Ideacity 2013 June 19 – 21 2013.


Kayleigh Platz
Kayleigh Platz
Kayleigh is a storyteller and researcher for Communitech, with a focus on sharing success stories. Born, raised and schooled in the Waterloo Region, she holds two degrees from the University of Waterloo. Kayleigh is passionate about social media, shoes and coffee.

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