Online dating: What your intentionally candid profile photo says about you

Today, I received a message on from a man who tried to woo me with the line, "Let love in. (I'm love)." There are several problems with that, but let's take a couple steps back: While writing "Money can buy you love, if you have a contract with this Harvard MBA," I spent roughly a month working with Happily Ever Afters' Jaime Richards to see her matchmaking techniques in action in my own life. The first step in modern dating is an online profile photo -- but this isn't just any photo.

It is, in fact, the perfect photo , but it shouldn't look perfect (just really, really good). Both Richards and Rachel Greenwald, whom I profiled for the article, frown upon their clients using a snapshot they have lying around. Instead, they advise paying for a professional photo, one that should appear candid but is actually anything but. If you follow their advice, this step is a necessity before even logging on to create a profile.

The goal of the photo is to orchestrate and present your best front: To this extent, Richards' clients visit a hairdresser in Cherry Creek and have their makeup professionally done before meeting a photographer. Greenwald's female clients are also required to purchase a new push-up bra before the photo session. But when it comes to their go-to photographer, both women use Marea Evans, a Denver-based freelancer with more than twenty years of photography experience.

"Most people think they can just use a flattering snapshot, but I'm on a couple of those dating sites just to see the imagery people are using, and I'm amazed at some of the poor, poor photos people are using to make a first impression," Evans says.

Evans is behind Greenwald's own headshot, which she took for her second book. "I'd say 99 percent of the photos I see I would never click on that person's profile. To me, it's the difference between being completely passed over and actually being looked at."

Before I met with Evans for my own walk-through of the process, Richards gave me a short list of hard-and-fast rules for creating an online dating photo. Don't wear a hat and sunglasses, don't use a photo of your cat or ex, put the beer down for the photo and for goodness sake, smile. There's no need to sex yourself up, she says, but you should wear comfortable and flattering clothing and stay away from crazy prints.

Look at Evans' photo as an example: In it, she is colorful without going off the deep edge, and though she has had her make-up done, this is not a prom picture. For my own photos, Richards asked me to send cell phone photos of outfits in my closet, which she eventually whittled down to a solid-colored dress and a flowery dress.

My shoes were problematic, but my glasses were even more so. For the shoot, I was directed to remove them while Evans took great care to make me comfortable in the natural lighting of her window-friendly home. (In the future, the fact that I am bespectacled every day could be a strange change, but the immediate goal is to make the best first impression possible, Richards says.) The resulting image is more flattering, less sloppy and closer to legally blind than I typically look on a day-to-day basis. After running it by friends and coworkers, the general consensus is somewhere between "listening to Al Green" and "writing an etiquette column." (Some of my friends are nicer than others.)

Great lighting is Evans' greatest strength and heaviest emphasis, and she reacts quickly to any nervousness on the part of her client in order to ease them into the situation. If you feel awkward, she says, you look awkward in your photo. "There's nothing worse than an uncomfortable subject because it shows in every single picture, Evans says. "You want that sincere, twinkle-in-the-eye, approachable-but-not-stiff photo, but it's not a glamor shot. You don't want it to look like you've hired a professional photographer, makeup artist and hairstylist to snap these photos, even though you have, and that's tough to do."

Although the process can be an expensive one -- Evans, for example, charges $250 for the photo session and $75 per photo you keep -- both Richards and Greenwald insist upon the practice and swear by its results. Once a client sits down (and stands up, and walks slowly, and poses laughing, and lounges idly) with Evans, they then work with their dating coaches to select the best photos. Richards can tell immediately which photos will be most successful: In one photo, I didn't notice an awkward stomach line, but she did -- and asked Evans to crop it out.

In the end, this first step in the date-coaching process should return to the same business focus Greenwald advocates in approaching your love life: You're selling yourself.

"If you're going to put yourself into this pool of candidates, you want to give yourself competitive edge," Evans says. "You wouldn't submit a bad résumé, so why would you submit a bad photo?"

More from our Follow That Story archives: "Matchmakers offer tips on how to sell yourself -- and why a matchmaker can help."

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Kelsey Whipple
Contact: Kelsey Whipple

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