A friend of mine is a true online dating Guru. Over many months, through trial and error, he learned everything there is to no know about the world of online dating. Now that he is in a serious relationship (with a lovely woman whom he met online) he serves as a type of online dating consultant to those in need; such as myself (at one point in time).

When discussing possible topics I could write about for my upcoming JDate blog, he threw out the idea of a Q&A type blog but I didn’t really feel qualified to write it. Later in our conversation, I floated out the idea of me asking him a series of interview style questions that might offer some advice to readers, which he was open to and seemed excited about.

So, in a JDate Blog exclusive, I present to you a Q&A with my friend “The Online Dating Guru.”

Q: Is online dating right for me?

A: It’s your call. If you view online dating as a stigma then it’s probably not right for you. However, if you view it as a way to meet cute, cool, interesting people who are outside your normal sphere of influence then you’ll probably have a good time with it.

Q: What should I put in my profile?

A: Be yourself; talk about your interests and what you’re looking for in another person. It is better to seem incredible to 10 people than generic to 100.

Q: What about photos?

A: You don’t need to go overboard in this section. A few photos that show what you really look like, preferably having fun, will do the trick.

Q: What’s the best way to talk to someone for the first time?

A: IMs are usually the best and most straightforward approach. Winks also provide an easy way to gauge the other person’s interest level without seeming creepy.

Q: I want my first conversation with someone to be really, really, special; how do I make that happen?

A: You can’t. Get over yourself.

Q: I keep exchanging a few emails but my conversations seem to all end abruptly; what gives?

A: It’s either one of two things. Either you are being too passive and not pushing the conversation along, or you are pushing too hard and freaking people out. Try to use the natural flow of conversation to move things toward meeting each other, and trust your instincts on when it is time to ask the other person to meet.

Q: I went out on a really amazing date and never heard from them again; what the heck?!

A: It sucks. It will always suck when you have a good date and then the person disappears off the face of the earth. Try not to take it personally. You never know what other drama is happening in their life.

Q: Why am I doing this again?

A: Because you want to meet someone. Because you want to go on walks to coffee houses and discover mutual interest in the same trashy ‘80s bands and ‘90s movies. You want to have hour-long conversations about nothing and feel something during that first kiss; and the second kiss. And if you’re not doing it for those reasons then do it for your mother because she’d love grandkids one of these days.