Wow, she’s really interesting as well as cute. I think to myself that if I could at least meet her, the thirty bucks I have to take out of my credit card to join would really be worth it.

That profile hooked me. I sit down and create a profile that I think describes me and upload a variety of photos that I think represent me pretty well. I excitedly send out a bunch 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 despondent checking an empty email inbox day after day, wondering if my send button was working.

After months of experimenting, I’m going on more dates than I have time for and meeting fascinatingly beautiful and intelligent women every week.

Success is all about showing your best face while standing out from the crowd of faces.

Part 1 – Images

A friend of mine once told me that she made sure to post photos depicting 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 failings or unflattering images online is a recipe for failure. The idea is to get them to know you, and then you have a chance 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 can be candid or less posed. If 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 doing sports to show your active and adventurous side. These should be flattering, but they’re usually easier to take or choose from your photo collection because they’re often not close-ups.

Part 2 – Profile

I am fun, optimistic, adventurous, down to earth and love life! Sounds like the perfect person, doesn’t it? Well then there are millions of people who are perfect for you because almost every online profile says the same thing in different ways. There are a lot of 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 to prove it. Examples from my profile:

Adventurous:

I once told a jungle shaman to put two cats in his mouth; He gave me a bit of 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 strange stares as I would have thought. No wonder I like a bad pun so much, at least I have a groan.

Open mind:

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

“You are an individual, just 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 going through their profile only to find a question to ask them. “I’m fun, lively and down to earth” leaves me with only the question “How are you like that?” 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 did not find anything that gave me more answers than another. In fact, the wittier, smarter, and more humorous he tried to be, the more he messed up. I made many discoveries throughout my online dating adventure. One is that email is much less important than image and profile. Here are some other ideas:

Nobody likes a form letter.

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

Keep questions in your first email short.

I hate closed questions (yes or no) in real conversations; they shut down the conversation instead of stimulating it. The interesting thing is that in an email no one will answer with just a yes or no, and since the question is short and quick, it is easy to answer. Start with a quick question like “When were you in Peru did you get to the Amazon?” They will respond to more than 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 tie it back to a very short experience or example of mine. Do not occupy more than one paragraph. Remember that the longer the email, the more someone will feel they have to reply to you. Short emails get more responses 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’m okay with that, the reality is that most of the time you’ll know in a couple of emails or after a phone call. Don’t be afraid to drop in for coffee at a public coffee shop after a few emails. In fact, it can be a huge waste of time to build a relationship over email or phone. I rarely meet someone who is the same in person as they are online, on the phone, or via email. Sometimes that’s a good thing, other times I found I liked the person too much only to find that in person we had no chemistry. I always tried to get two or three emails from me and then suggested we meet 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 the task and was often surprised that I liked them more than I would have thought. However, online dating is a numbers game even more so than meeting people in real life. Don’t get too attached to getting a response 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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