Wow, she’s really interesting as well as cute. I think to myself that if I could just get to know her, the thirty dollars I have to draw from my credit card to join would really be worth it.

That profile hooked me. I sit down and put together a profile that I think describes me and upload a variety of photos that I guess represent me pretty well. I am excited to send a ton of emails to everyone I want to meet in anticipation of some amazing dates.

Twenty unanswered emails later I cancel my account; I admitted defeat. I didn’t meet the woman I expected to meet; I didn’t even get a date. My first attempt at online dating was a complete failure. I was bummed out checking an empty email inbox day after day, wondering if my send button was working.

After months of experimenting, I’m dating more than I have time for and I’m meeting amazing, beautiful, smart women every week.

Success is about putting your best face forward while standing out from the crowd of faces.

Part 1 – Images

A friend of mine once told me that she made sure to put up photos that represented her in a variety of looks, so no one would be surprised when they met her. She didn’t want to present only the best shots of hers. While I applaud her sense of honesty, people online have a “Next!” mindset. Any little thing will cause someone to delete your email or bypass your profile. Showing up for both the good and the bad is great in person and actually makes you more attractive. Posting your flaws or unflattering images online is a recipe for failure. The idea is to get them to know you, and then you have the opportunity to find out who that person is and vice versa.

The most successful online daters are the people with good photos. If you’re serious enough to try online dating, be serious enough to take some professional photos. Don’t take glamorous photos, have the photographer take photos that may be candid or less posed. If it is done by a professional, the photos will be much more flattering. Black and white close-ups are a very flattering shot to add among your other photos as well.

Try adding some photos of yourself on your travels or playing sports to show your active and adventurous side. These should be flattering, but they’re usually easier to take or pick from your photo collection because they’re often not close-ups.

Part 2 – Profile

I’m fun, optimistic, adventurous, down to earth and love life! Sounds like the perfect person, right? Well then there are millions of people perfect for you because almost all online profiles say the same thing in different ways. There are many tips on how to write a good profile, but I want to give you a format to write something really interesting and different while still presenting who you are.

Start with one of those character traits about you. Instead of just saying that you are, give us an example with a quick anecdote that proves it. Examples from my profile:

Adventurous:

I once told a jungle shaman to put two cats in his mouth; He gave me a little embarrassment when I realized what he had said in Spanish.

Goofy:

I find that doing a John Travolta dance move in the middle of a busy intersection doesn’t draw as many weird looks as I would have thought. No wonder I like a bad pun so much, at least I get a groan.

Open minded:

The strangest person I’ve ever given a hug to was the man who did an upside-down handstand for hours with his head in the bottom of a corona bottle in Union Square last year. He was standing by sharing with me his philosophy of upside down people in an upside down world, and I appreciated the poetry of his slightly crazy worldview.

“You are an individual, like everyone else.”

The key to profiling is to stop TELLING THEM who you are and instead SHOW THEM who you are with examples and experiences. There are a lot of adventurous people out there. How do you manifest that?

Don’t explain every detail. Leave some mystery; give them something to ask you about. Make it easy for them to email you with questions. There was nothing more frustrating for me than finding a person I liked and then scrolling through their profile only to find a question to ask them. “I’m fun, lively and down to earth” leaves me with just the question “How are you like this?” Unfortunately, that’s too big a question for a first email.

Step 3 – Email

I wrote a lot of interesting, witty, funny, insulting, and weird emails, all in an attempt to get answers. In the end, I found nothing that gave me more answers than another. In fact, the wittier, smarter, and more humorous he tried to be, the more he screwed up. I made many discoveries throughout my online dating adventure. One is that email is much less important than picture and profile. Here are some other ideas:

Nobody likes a form letter.

Actually read the profile for a quick question about something they put there.

Keep the questions in your first email brief.

I hate closed questions (yes or no) in real conversations; they close the conversation instead of stimulating it. The interesting thing is that in an email nobody will answer with a yes or no, and since the question is short and quick, it is easy to answer. Start with a quick question like “When you were in Peru did you get to the Amazon?” They will respond to more than a one-word answer, but they won’t feel like they have to write a book. If you ask “How was your experience in Peru?” they may just put your email on hold for when they have more time to respond. I hope they find that moment.

Keep all your emails short.

I like to ask a quick question and then relate it to a very short experience or example of mine. Do not take up more than one paragraph. Remember that the longer the email, the more someone will feel like they have to reply to you. Short emails get more response than long emails.

Build relationships in real life, not online or over the phone.

The Internet is a scary place. Many people recommend taking your time getting to know someone before meeting them in person. While I agree with that, the reality is that most of the time you will find out in a couple of emails or after a phone call. Don’t be afraid to stop by for coffee at a public cafe after a few emails. In fact, it can be a huge waste of time to build a relationship over email or over the phone. Rarely do I meet someone who is the same in person as they are online, on the phone, or by email. Sometimes that’s a good thing, other times I found I liked the person too much only to find out that in person we had no chemistry. I always tried to get two or three emails from me and then suggested we meet up for coffee.

Put these online dating tips to work and start getting better dates!

Be careful and don’t take it too seriously. I found that the people I was most excited to meet were often not up to par, and I was often surprised that I liked them more than I had thought. However, online dating is even more of a numbers game than meeting people in real life. Don’t get too attached to getting an answer or date from just one person. If you keep that in mind and realize that it can be very empowering to have more dates than you have time for, online dating can be a very rewarding experience. You never know who you might meet!

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