I signed up for online dating in 2008 after a not-so-subtle suggestion from my mother, who was tired watching me date Mr. Wrong. She suggested I try it for a month, "just for fun."

Naturally, I was skeptical. I made a profile, uploaded some photos, and waited. After wading through a discouraging pile of creepy winks and lewd comments, I received a message from a Jewish guy who was in culinary school.

He'd read my profile and noticed that I REALLY loved food. He sent me a list of great restaurants in the city that "someone" could take me to. It was clear he did not expect to hear from me.

Intrigued, I wrote back, “Thank you for the list. Now, hang on, who are you?”

We messaged back and forth a few times before I gave him my phone number.

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He texted me within five minutes and I giggled knowing how many of my dating rules he had just broken. I married him this April and would like to pass on some of my online dating tips for those of you who are still in the field.

1. Don’t be TOO compatible.

Spoiler alert: liking all the same things is boring. Sure, there's something to be said for compatibility in certain areas like location, education or religion (if it’s important to you). But looking outside of your interests is what makes things interesting.

There is nothing hotter and more fun than learning something new from the person you're dating. Plus, having different interests will allow you to keep your individuality in the relationship instead of slowly morphing into the same person. Do you love camping and he's never left the city? Does she love yoga and you can’t touch your toes? Go for it! Who knows? You might discover something new about yourself.

2. Be open to dating someone who is not your type.

Whether we think so or not, most of us have been dating some derivative of a "type" for years. For me it was tall, athletic, emotionally unavailable men with whom I'd spend months/years trying to fix. Yeesh. The beauty of online dating is that you have a clean slate. You can take your time and don’t have to settle for your old standbys.

Well, you can take this advice or leave it, but I challenge you to strike up a conversation with someone intriguing who is outside of your comfort zone. The worst that can happen is that you get a funny story out of the whole thing.

3. Have fun with it! (Even though online dating can feel like a second job, it's not.)

I know people who treat online dating like it’s a grueling, demanding and unpleasant chore. Putting this kind of pressure on yourself is detrimental to your personal growth and happiness!

Having an online profile just allows you to be a little more available to the world. It's not that much different from meeting someone in a bar. You're both in the same place at the same time and interested in meeting new people. Open yourself up to the possibility of meeting someone compelling, create a profile that makes you proud, and, lastly, keep on living your life!

4. Know that you can learn a lot about potential dates from the picture they choose to use.

I will never forget my now-husband’s profile picture. He was dressed in a striped button-down and jeans and sitting on a swing. Yep, a swing. He looked elated, relaxed and adorably secure. Thinking about that photo now still makes me smile because it really did sum him up completely. He is funny, playful and doesn’t take himself too seriously.

I didn’t know it then, but that was exactly what I was looking for. Sure, the guy with the abs taking a shirtless photo of himself in the bathroom mirror is attractive, but if that is really what he wants to say about himself … do you really want to sit through an entire date with him? I’d rather give the guy with the pink squirt gun a shot.

5. Send your interest an obscure questionnaire.

It almost doesn’t matter what he or she answers. What you want to pay attention to is their approach. Do they get defensive, excited or silent? Some ideas for question:

  • What’s the best memory you have from your childhood?
  • What’s your guilty pleasure?
  • If you could live anywhere, where would it be and why?
  • When was the last time you laughed really really hard?

This is fun because it gets people out of their profile and into their real lives. The more fun they have with the answers, the better the actual date will be.

Oh, and don’t be surprised if they come back with some fun questions for you!

6. Don’t get discouraged, but accept that dating is HARD.

We get dressed up, meet a stranger and lay our hearts out on the table in hopes of finding a real connection. Sometimes it takes months and sometimes it takes years.

I do, however, promise you that it’s worth the effort. If you have a bad date experience, don’t let it ruin your whole idea of dating online or otherwise. Just take a break, shake it off and try again. If you leave the door open long enough, the right person will walk in.

Good luck and have fun!

Photo Credit: Getty Images


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