I was hanging out with a friend of mine in Brooklyn over the weekend, and he’s getting back into the dating scene. He was pretty stung by a woman nearly a year ago, and is finally over it.

He and I got to talking, and I convinced him that for someone getting back into action, or who is totally new, internet dating is a MUST to get you going.

Anyway, so I pulled this list of my 5 best online dating tips together for him – but thought to flesh it out a bit into a new blog post.

Here were my thoughts…

5 Online Dating Tips for Men

Did you know that a few years ago, Mystery, Style, TD and I all posted profiles online?

We decided that if we were going to call ourselves dating coaches, we’d have to know about everything related to the topic. So, we each picked a service (Nerve, Lavalife, Match) and posted a profile.

As you can well imagine, we found out some pretty amazing stuff.

I gotta say, I was a bit uncomfortable initially in posting my picture online. What if someone recognizes me? What if my ex-girlfriend sees this? What if someone forwards this to MY MOM?

Well, after I got over myself I realized that no one in the world really cares so much to check and see if I have an internet dating profile up, and even if they did, they would also have a profile posted so we’d be all even anyway. Right?

So, after a month or so of some pretty wild dating experiences, we pulled our notes together, and created a list of 5 MUST have’s for the ultimate internet dating advantage.

Alas, here they are:

Online Dating Tip #1

Recruit a friend.

This is number one for a reason. It is always better to have a buddy help you set up your profile, as they will have a better idea of the strengths you should highlight.

They can also help you gather #2 (see below). Mostly, you will have more FUN with a friend going through this with you.

You can share stories afterwards, even make up friendly competitions to encourage you both forward.

If you don’t have a buddy interested in doing this with you, don’t let it become an excuse. You can always go to one of the dating advice webboards and find someone there but only if you’re really determined to get out in front of the competition.

Online Dating Tip #2

It’s all about the pictures.

You’ve gotta have GREAT pictures to be out in front of the competition online. I always recommend four, in these categories:

• 1 which is a basic headshot, so she can get a clear idea of your face;
• 1 of you in your element (so, if you’re a hiker, a shot of you in the wilderness);
• 1 of you with GIRLS (women friends, sister(s) etc);
• 1 of you dressed up and out socially (office party, wedding, bar mitzvah, wherever).

If you don’t have these, that’s fine.

The idea here is to have four pictures of you in different environments/settings. If you need to enlist the help of a friend, feel free.

Online Dating Tip #3

Funny headline.

A pic and a humorous headline are critical. Please, please don’t be boring from the start.

What impression does this create in the mind of a woman? Not a good one.

Be unconventional, and surprising, avoid the obvious.

Got it?

Online Dating Tip #4

Sincerity and vulnerability.

At some point in the course of the profile, you will be able to write a bit about yourself. Feel free to mix in some truth with the humor.

If you’re afraid of something, mention that. If you’re just getting back out there, mention that.

If you’re terrible at dancing, mention that.

In other words, endear yourself by revealing that you are human.

No one is perfect, and guys who gloat and posture online about how much money they make, and how big their car is are sorted through like junk mail.

Online Dating Tip #5

First date, not a date.

Last but not least the first date is not a REAL date, OK?

The first date is basically when you are introduced to the girl. The second date is really the first date.

So, keep your first real-life encounter short and sweet.

I always like to ask girls out for dessert, after a dinner meeting (which may or may not be true, but NEVER take an online girl out for dinner when meeting her for the first time).

This way, we get a low pressure way to meet-up, and can decide if we want to get together for a real date later on. Think of the first meeting as when you are introduced at a party.

If you find that the conversation flows after the first awkward moments, then a first real date is a must.

I had some great experiences in online dating and found it was a great way to practice social skills. I also met some really cool girls, and had a load of fun.

Also, the Project Hollywood guys and I got to swap stories after the fact, which helped us bond too as roommates.

If you don’t have a profile online and/or have had some bad experiences in online dating, let me recommend that you take a look at my pal Dave M’s killer program “Insider Internet Dating”.

He will walk you through all the steps:

• Setting up your profile
• Choosing awesome pics
• Sending killer first messages that get opened
• Moving things FAST to an in-person date
• Even revving things up sexually so you know that the connection will never slide into the dreaded “friends” territory

You can learn more by clicking the link below:

Dave M’s “Insider Internet Dating”

Remember, you have nothing to lose and everything to gain by doing internet dating.

Even if you don’t meet the woman of your dreams, you get to go out on some dates, meet and talk with live women, practice social skills and have fun.

Good luck!