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Six online dating lessons learned the hard way

Six online dating lessons learned the hard way. Photo: Getty

I've always been averse to online dating. Everything about it seems so impersonal, so unoriginal, so I've totally given up on finding love so I'm just going to throw myself, stripped of all pride, into this sea full of flailing fish.

Then I moved to New York City.

NYC, a booming metropolis with countless potential suitors. NYC, where, despite being surrounded by men on every single street corner, grocery store, and subway car, I was still spending my Friday nights with Netflix, or with the small group of friends I had amassed. Saturday nights, too, come to think of it. It wasn't long before I caved, and signed up for three different dating apps.

I'm sorry to report that so far, my efforts have gone unrewarded. I've been robo-matched with men who don't pick up where the algorithm left off. I've had a few one-off dates that left me cold. I have the beginnings of carpal tunnel syndrome from all the left- and right-swiping. What am I doing wrong? Lucky for you, I allowed several dating coaches to tear apart my approach, and my profile. Learn from my mistakes…and enjoy the plentiful fish.

Lesson No. 1: Save the group photos for Facebook.

If a guy wanted to play Where's Waldo he'd buy the book, so don't make him pick you out of a group photo on your dating profile, says Lisa Copeland, dating coach and author of ‘The Winning Dating Formula for Women Over 50: 7 Steps to Attracting Quality Men’. Your photo should be only of you, without any distractions. But steer clear of selfies as well, which are just plain awkward. Instead, grab a friend, some favourite outfits, and get snapping, suggests Tracey Steinberg, a New York City–based dating coach. "Make the experience fun and have her take some photos of you just authentically being happy," says Steinberg.

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Lesson No. 2: No one cares about your life story (yet).
"A profile is really just to get someone to step up to the plate and say, 'Hi, I want to meet you,' " says Copeland, so keep your "about me" section to two to three short paragraphs, max (or five short sentences, if you're using a dating app). Say a few things about yourself, what you're interested in, and what you're looking for. But be specific—instead of just saying you like to read, offer up the name of your favourite book. "It gives the person who's reading your profile a better understanding of who you are, and it gives them something easy to ask you about," says Steinberg. Copeland suggests ending your profile with a scenario that the prospective mate can imagine himself in with you. "Men are visual and they like to imagine themselves in someone's life, so end your introduction with an invitation," she says. Try something like ‘Let's spend Sunday brunch mulling over 2-across.’

Lesson No. 3: Give up on height requirements and similarities to previous partners.
We all have a type (special shout-out to men with great hair and awful communication skills). But if you keep ending up with the same heartbreaking results, maybe it's time to broaden your search criteria. "Women have this picture in their heads of who they think they want, and it's usually the last person they were in a relationship with," says Copeland. Try wiping your slate clean and getting rid of any preconceived notions of who your "Mr Perfect" is. "We always think certain qualities will make us happy, but it's usually how a person makes us feel - when we're with him and when we're not - that makes him a good match," says Copeland.

Lesson No. 4: There's a little retro game-playing in order (just a tiny bit).
I have to admit that I struggled with this recommendation. I fully embrace 21st-century female independence (do I even need to say that? It seems like a foregone conclusion by now), so when multiple experts suggested letting the guy set the first date, the feminist in me recoiled. No, forget the feminist; I recoiled. But Copeland assured me that it's not about surrendering your power, but about knowing how men's minds work (not to generalize or anything). "It's not that men want a woman who's a doormat. They just want to play their role as men, as protectors and providers," says Copeland. That's not to say you have to be totally silent online; go ahead and reach out to people who interest you. "If you just put up a profile and wait around for someone to message you, you're not being proactive in your dating life," says Laurie Davis, founder of eFlirt. But after getting in touch, let him ask for your number or make plans to meet up for drinks.

Lesson No. 5: It's all about divorce-ifying.
Sorry, I meant diversifying. There's a big difference between dating and being in a relationship, and if you're not in a committed, exclusive partnership, it's OK to date more than one person. "Everyone dates multiple people. You need to take advantage of every opportunity - and there are going to be multiple opportunities," says Davis. But it's not just about keeping up with other daters - it's a way to slow down your emotional pace with a new person. "The other person is probably dating other people, and if you're not, you're already putting more effort into the relationship than the other person is ready to commit to," says Davis - and we all know how awful it feels to be in a one-sided relationship. Plus: Going on multiple dates with multiple men is incredibly empowering. Instead of constantly checking your cell for messages from that one contact (and sending "test" messages to your friends to make sure it's still working), you get to choose who stays in your life and who doesn't.

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Lesson No. 6: Know who you are -and embrace it.
It should be obvious, but we all forget this one from time to time: Changing yourself to match the likes of someone who looks really good on paper (on "paper," I mean) is only going to backfire. So the most important rule of dating, above flattering profile pictures and witty "about me" sections, is owning who you are. Which is admittedly easier said than done. "If you're not comfortable with yourself, it's going to be hard to be in a relationship, and even harder for someone else to be comfortable with you," says Davis. Knowing what you want and what you don't want out of a relationship helps, too. But, as always, when in doubt, trust your gut. "Never waste your time on someone who isn't confident or available to you; if something really doesn't feel right, love yourself enough to know that you deserve better, and move on."