How to hack the online dating game: 10 tips from the woman who cracked the code

I have a new hero: Amy Webb. She’s a data-loving CEO of a technology company who, since giving this TED talk, may be forever known as “the woman who hacked online dating”. So how did she do it?

Apparently Webb was having very little luck online dating. The guys she liked didn’t write her back, and her own profile attracted less-than-desirable prospects. So naturally, she turned it into a data experiment and geeked out on spreadsheets. After laying out 72 key data points, creating multiple fake male profiles (you gotta check out the competition!), then collecting enough data to create her own “super profile”, Webb suddenly became the most popular gal on the site. The story ends nicely with Webb meeting her future husband and accomplishing her must-start-having-kids-by-35 timeline. 

Here’s Amy’s 10 rules for online dating (along with a bit of personal experience):

1. Use aspirational language. Keep your words positive, inspiring and optimistic. Be open about your hopes, dreams and passions and keep things that may be controversial to yourself (you can always reveal more later). Online dating starts off like window shopping—avoid anything too heavy or serious. A good rule of thumb is to read your profile top to bottom, and if you see anything that sticks out as negative Debby Downer talk, take it out. Better yet, find a better way to spin it in a positive light.

2. Keep things short and sweet. Aim for between 90 and 100 words (3-4 sentences). Choose your words carefully and be succinct. Please don’t be that person who writes “Hmmm….I’ve never been good at talking about myself.” If you’re not a good writer, figure out the keywords and points you need to make, then ask a friend to help you out.

3. Use amazing photos. Show off your eyes and your smile, and be sure to avoid using a picture of you in sunglasses as your main profile photo. Photos should focus on your waist up, unless you have a great figure. Then it’s OK to include one or two full-body shots in your gallery. Most of your photos should be close up so people can see your face—this is where much of the initial “would we have good chemistry?” is determined. Avoid cropping your photos, lest you end up with the dreaded way-too-vertical “I was standing next to my ex” photo.

4. Don’t try to be too funny. If you want to use humor, write whatever you’re planning to say down and show it to some friends or coworkers first. Have them read it aloud. With your tone of voice and inflection, it may be hilarious—but out of your friend’s mouth it may fall flat or even be offensive. Save the humor until you can wow them in person.

5. Don’t use specifics. Avoid mentioning specific comedians, shows, books, musicians or movies unless those are top-tier attributes on your list. It’s possible to be generic about what you like while still being specific enough to sound interesting. Just because you like Louis C.K. or Kid Cudi doesn’t mean that a potential suitor does. Unless that comedian is one of your deal-breakers, leave him or her off your profile.

Amy Webb’s TED Talk

6. Avoid taboo topics. If there’s something in your life or personality that may be controversial or taboo, leave it off your profile. Perhaps you are an avid NRA member, are passionately Pro-Choice, or a strong advocate for medical marijuana—you may want to leave out things that someone could potentially interpret that information in a way that disadvantages you. Odds are you may turn off more people than you attract.

7. Save your accomplishments for later. If you’ve won a Pulitzer or climbed Mount Everest or for some reason own a jet, this is wonderful news—just don’t share it online. These are the types of details to work into a conversation on your first or second date. If someone introduced himself to you at a party, would the next thing out of your mouth be items off your resume? Of course not, so don’t act that way online. Let your personality win someone’s interest, not your bragging rights.

8. Flirt carefully. Be mindful while flirting online, since it’s easy to sound too aggressive too soon. The best way to flirt is to care deeply about whatever your date is saying and to focus all of your attention on him or her. We’re flattered when people throw attention our way. So ask thoughtful questions. Take a keen interest in the conversation. Be enthusiastic. When writing an email or text message, as a general rule only say things you’d feel comfortable and natural saying in person.

9. Use the 20 hour rule. If someone instant messages you while you’re online, go ahead and IM back if you want. Otherwise, wait 20 to 23 hours between e-mail contacts for the first few messages. Webb found that successful daters waited that amount of time and as a result still seemed eager without coming off as desperate.

10. Don’t act like a stalker. Avoid sending any messages while most people are sleeping, even if you’re wide awake. Shoot for business hours or evenings.

 

Buy Webb’s book Data, A Love Story for the full download.

 

What has worked best for you in online dating?

Any tips you’d like to share?

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