I don’t normally read Marie Claire, but with an attention-grabbing headline like “Why You’ll Never Find Real Live Online”, how could I resist reading more?

After spending a decade at Match.com and Yahoo Personals writing compatibility formulas, psychologist Mark Thompson had fallen out of love with his work. “Early on, there was real enthusiasm that we were going to figure out how to bring people together,” he says. “But now the industry is so competitive that it’s more about what sites claim they can do than what us eggheads could actually do for people.”

MC: What made you leave e-dating?

MT: I hated the way we overpromised and underdelivered. Our studies showed that the odds of meeting someone online and dating him more than a month are roughly one in 10. So it’s great that all those people on the TV commercials met their spouses, but they are the exceptions, not the rule. No computer can accurately predict whom you should be with. The function of the math will make vastly more false predictions than accurate ones.

Computerized matchmaking has been around since the 70s (at least, I remember an episode of Three’s Company that had Chrissy feeding punchcards into a machine in order to find her ideal date). Mark Thompson has spent a decade trying hard to hammer those algorithms into shape to help people find true love—and he’s throwing in the towel. That sits well with how we feel at Wingman—the concept of profiles, and sitting at home shopping for your perfect mate really misses the point of finding true love.

MC: But doesn’t happiness have more to do with emotional compatibility?

MT: Sexual compatibility is a keystone to a relationship’s long-term success, and it requires three things: a similar emotional approach (positive, friendly, and fun, or dark and mysterious); a similar activity levell (fast and active, or slow and mellow); and a complementary power dynamic (strong, confident, and powerful, or gentle and submissive). These qualities often line up with what you want interpersonally, too.

Wingman allows for real-world interactions, and discovering new people by checking-in around town. Wingman makes it easier to flirt with and meet the people who hang out at the same spots that you do—hopefully discovering the three tenants that Mark identifies above: emotional approach, activity level, and power dynamic.

The migration from Myspace to Facebook was a dramatic shift away from the Profile Penalty. Facebook created a new network defined by actual friendships, school/work relationships, and common interests, instead of Myspace’s intricate, cumbersome Profiles that took a great deal of time to polish and perfect.

The problem I have with dating websites is that they attempt to use a series of profile questions to lock down your personality, your romantic interests, and your compatibility with the other users on the site. I can’t tell you how many times I see a profile that I like, only to nitpick and find the one or two (or three…) “dealbreakers” buried in the details of someone’s profile.

I call this the “Profile Penalty”. Maybe it’s a misspelled quote. Perhaps it’s over-exuberance around a reality TV show that I hate. Maybe I read too much into the “What I’m looking for section”, and deem this prospective mate to be too slutty/too prudish/too boring.

Or, I find the profile of my perfect mate. Oh great, now what? Now I must craft the perfect witty-but-not-overbearing, perfectly-worded-yet-casual introduction message. What if they don’t respond back? Am I unattractive, or are they just on vacation?

Wingman has no Profile Penalty. Just upload a photo, and check-in at a few places. See someone you like, send a Wingman. No profiles—just rejection-free flirting.

We are instinctual creatures, and can infer a great deal about someone based on what they look like and where we see them. By removing the Profile Penalty, we shift the burden of getting to know someone out of the profile and into real life.

Sure, you can spend several hours perfecting your online dating profile, and then spend many hours at home searching through others’ profiles, looking for that perfect someone. Or you can use Wingman, and check-in as you go about your daily routine (and nightly adventures) and see who might cross your path.

Over on Urlesque, Kia Matthews outlines the types of repeat offenders one finds on dating websites, such as “A 27-year-old ‘consultant’ who lists Happy Hour as one of his talents” and “The Uncle Ted, who on a Friday night ‘You Can Find Me: Swing Dancing.’” I’m happy to say that we don’t have “types” on Wingman. We just have people hanging out, mingling, chatting. Read more at The 11 Guys You Meet on Dating Sites.

“Online dating”, “internet dating”, “iPhone dating”, “Foursquare for flirting”, “mobile geolocation mingling”. Too much geek speak, not enough flirty fun. The problem I’ve found with many online dating tools is that they focus too much on the technology and not enough on the good part—meeting new people.

As we’ve worked tirelessly to develop Wingman over the last 6 months, my partner Jim and I have done our best to not get too sidetracked by technology. As a developer, it’s easy to obsess over the technological implementation of an app like Wingman, the bells and whistles provided by the iPhone SDK, and the complex interactions that we’ve designed to provide optimal user experience.

What makes Wingman different? We have spent a great deal of time reaching out to real users, to understand their desires, their needs, their concerns, their goals. We have designed Wingman to be a lightweight, easy-to-use tool that provides a straightforward way to anonymously flirt with people who hang out at the same places as you. The most important thing we can do is listen. We’re listening.

My iPhone is filled with dozens of dating apps (competitive research, I swear!) and it’s amazing how many of these tools are riddled with crazy technological implementations that make the apps nearly impossible to use. I can look through my phone and see the nerds on the other side who made the app. Poor nerds.

So many apps are designed by “dudes”, for “dudes”, with “non-dudes” as an afterthought. Although technically Jim and I are “dudes”, I know we’ve done our best to create a balanced, attractive, appealing application that all shapes, sizes, ages, genders and orientations will enjoy using.

In building a complex mobile application like Wingman, I must admit at times we may temporarily lose sight of our primary goal—to help people connect, flirt, laugh, love and live happily ever after.  It’s easy for us to spend entirely too much time nailing down spot check-in algorithms, push notification edge cases, and photo flagging rules.

OPW recently asked a group of kids aged 4 to 8 years old, “What does love mean?”.  Their answers are cute and hilarious and insightful and playful—many of the attributes that ring true even for the 20- and 30-somethings who use Wingman to find love:

‘Love is when a girl puts on perfume and a boy puts on shaving cologne and they go out and smell each other.’

Karl, 5

‘Love is what’s in the room with you at Christmas if you stop opening presents and listen.’

Bobby, 7

‘Love is when you tell a guy you like his shirt, then he wears it everyday.’

Noelle, 7

‘When my grandmother got arthritis, she couldn’t bend over and paint her toenails anymore. So my grandfather does it for her all the time, even when his hands got arthritis too. That’s love.’

Rebecca, 8

‘Love is when you go out to eat and give somebody most of your French fries without making them give you any of theirs.’

Chrissy, 6

‘When someone loves you, the way they say your name is different. You just know that your name is safe in their mouth.’

Billy, 4

‘Love is what makes you smile when you’re tired.’

Terri, 4

‘Love is when my mommy makes coffee for my daddy and she takes a sip before giving it to him, to make sure the taste is OK.’

Danny, 7

‘If you want to learn to love better, you should start with a friend who you hate,’

Nikka, 6

‘Love is when your puppy licks your face even after you left him alone all day.’

Mary Ann, 4

‘When you love somebody, your eyelashes go up and down and little stars come out of you.’

Karen, 7

Online dating, flirting, romance doesn’t need to be sketchy, creepy, stalkery.  People shouldn’t need to subject themselves to unwarranted attention, rudeness, naughtiness or grossness.

People are people, of course, but we’re hoping that Wingman brings out the best in people.  Sort of like Burning Man, or having a nice conversation with the woman at the Post Office, or sitting next to a cool guy on a flight—these experiences remind us that it’s fun, rewarding and stimulating to have random interactions with humanity.

Wingman makes it easier to kick start these interactions, by allowing you to express your interest anonymously, and by giving you some icebreakers to use when chatting.

Here are some ways that we’re hoping folks will use Wingman:

• send a Wingman to that guy in your office that you’ve been smiling at in the elevator.  Is he interested (and single, and straight)?
• send a Wingman to the girl at the other side of the restaurant, who is enjoying Happy Hour with her work friends.  Why does she keep bashfully looking over?
• send a Wingman to the guy who’s always walking his cute dog in the park in the morning.  You sometimes cross paths, but you haven’t even asked his name.
• send a Wingman to the girl who was dancing with you at the concert last night.  Her smiling photo at the venue’s spot screen reminds you of how much fun you had together.
• send a Wingman to the boy who sits 2 rows in front of you in history class and sometimes asks you how your day is going.
• send a Wingman to the girl who cheerfully makes your morning latte, and who always compliments you on your hair.  Is it innocent flirting or something more?

Wingman isn’t just for the shy, or for the meek.  Wingman is for anyone who is looking to have more fun, meet more people, and live a richer life by expanding their social circle—that’s what technology’s all about, right?

It probably comes as little surprise that Jim and I are avid Foursquare users. We’ve also enjoyed using Gowalla, Loopt, Hot Potato and a few other interesting location-focused mobile social networking apps. Some are shiny, some are interesting for a day or two, but only Foursquare provides real utility to me.

Friends and friends

I use Foursquare as a way to quickly share my whereabouts with my big-F Friends (e.g. real life people who I enjoy hanging out with) and my little-f friends (e.g. acquaintances and Twitter followers/fans). In a few short taps, I can broadcast my location, either to entice friends to join me (Happen to be near Vlada? Come join me!), to share an interesting experience (First rooftop BBQ of the summer!) or sometimes just to bookmark a place to help me remember it later (Great Thai restaurant in Chelsea!).

The core value of Foursquare is the same as Twitter and email and Facebook—to share life experiences with your Friends and friends.

Wingman helps you meet new people, in a safe, fun, anonymous and lighthearted way.  There’s no need to link to your social network, there’s no need to broadcast your flirting activity to the world, it’s smiling people tapping on smiling photos to smile some more.

Rewards

I find it interesting how Foursquare attempts to add value to checking-in, by bribing users with gimmicky status (“I’m the Mayor of Dunkin’ Donuts!” or “I just unlocked the Crunked Badge!”)

What I love about Wingman is that we don’t need to bribe or reward users to check in—you check in on Wingman to meet other people. The more you check in on Wingman, the more photos you leave of yourself around town, and the more likely you are to meet real people in real life.

Maybe I should capitalize that: Wingman helps you meet Real People in Real Life.

One of the things I love about Wingman is its simplicity.  Load it up, tap on photos, send your Wingman.  No worrying about if your profile is too big or too short or too eager or too distant.  No second-guessing if you really were honest in your description of yourself (and what you’re looking for), whether you spelled everything in your profile korrektly, or whether including Superbad in your list of favorite films is a turn-on or a turn-off to a potential match.

As we develop Wingman, we are constantly reminded of all the problems with traditional profile-based, sit-at-home online dating.  For example, Diana Bocco at eHow wrote a great overview of what she considers to be the Disadvantages of Online Dating.  She outlines 5 gripes which Wingman does a great job of avoiding:

• Deception – Wingman only works if you look like you do in your photo.
• Chemistry – Spotting someone across the room is a surefire way to tell if there’s chemistry.
• Flirts – Wingman is all about rejection-free flirting.  Flirt away, have a conversation, and don’t stress about whether you’ve met your soulmate.
• Distance – Wingman helps you meet only those people who visit the same Spots as you.
• Cost – Wingman is free like Sunday morning.

Wingman is a fun way to meet real people in real places. By removing the stress of profile-based, sit-at-home matchmaking services, Wingman allows for fun rejection-free flirting with people, not profiles.

I recently found another great article listing Ten Complaints About Online Dating Services.  So many unhappy souls out there looking for a bit of romance!  Well, Wingman is here to help:

• I don’t know how to start a conversation online. Why have an online conversation when you can just go over and say “hi”?  Real people in real places.
• I don’t know what to write about myself. We make it easy by encouraging simple stress-free multiple-choice icebreakers.
• I get way too many people contacting me online! With Wingman, you only make connections with people that you’ve expressed interest in.
• All the people I meet online are losers; nobody is compatible with me. Wingman users are a fun attractive bunch.   We focus on people, not profiles.
• I keep getting rejected by people online. Sending your Wingman means rejection-free flirting in both directions.

We’re excited about the possibilities for Wingman, and hope to create a rich new way for people to meet without the hassles of online dating.