Online Dating: Getting Out of the Inbox.

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People that know me know that I date. They also know that a lot of these dates come from the interwebs. You see, I’m a member of a few different dating sites. They’re all free and what not and that’s how I choose to roll. It’s not that I’m cheap, but my best dates have all come from free dating sites.

I do have some guidelines for myself, where it concerns meeting a girl online. I’ll share them with you. You can use what works and cross out what doesn’t, of course, to suit your needs. Here are some things that I’ve observed:

  • Women who post bikini pics of themselves, seldom have anything really interesting to talk about
  • No one wants to wait a month before they meet someone they me3t online for the first time.
  • Online dating is best when it’s kept short and sweet. Get to the point!
  • A “grocery list” to find your perfect mate is lame.
  • Stalking is a bit more creepy online, it turns out.

Here are some of my own guidelines for online dating. Keep in mind these are just my own opinion.

  • Don’t send a ‘form’ message. Don’t send a pre-written message to 100 different users thinking “Oh, well at least one of those people will call me or write me back.” Women can see through this sort of b.s. Whoever you want to send a message to, take time to make it unique. Look at the person’s profile. Take a look at their interests, comment on them and ask questions. It’s a great way to start off a message. Just be unique every time.
  • Try to keep the emails fresh and funny, but also keep it quick. Either the second or third message, if not sooner, provide your number and ask for your interest’s number as well. I wouldn’t start off with a full on message that includes your life story.
  • Arrange a phone call, if possible. It’s hard to really flesh out someone unless you meet them face to face right off the bat. The next step; and certainly next best thing, is to have a conversation with them on the phone. This will tell you, to some degree, how your personalities mesh.

Here are some messages I’ve sent out to girls that have resulted in dates:

“Did you know that Chuck Norris was what Willis was talkin’ about?”

Crazy, huh? =)

So I read your profile and I liked what I read. You seem really cool, the kind of girl I’d like to get to know better. And, it doesn’t hurt that you’re a lot prettier than I am. =)

Anyway, if you are interested shoot me a message and say ‘hi’ yourself. If not I’m going to start throwing children into the sun, just like Chuck Norris.


The above message was one that I wrote to a girl online. The message here isn’t too specific, it’s short and to the point with some Chuck Norris humor interjected. But, you see, that’s the important piece. This person’s profile had a few Chuck Norris quotes written within it. By including a couple of Chuck Norris quotes in my message, I’ve shown this person the following:

  1. She knows I read her profile and took time to write an original message
  2. She knows that we share a similar sense of humor, if not a serious bromance for Chuck.

Here’s a second message I wrote to someone:

Carlie Simon Jr.
You wound me; telling me you don’t know your Darm Kahplagh from your Deet Krum Sothpragma! For shame, Carlie, for shame. =)
I’m glad that we agree the new trilogy sucks as much, if not more than, a very ugly and desperate male prostitute selling it off at leisure world.

Seriously though, I would like to talk to you more. You think exchanging IMs or *gasp* numbers would be okay with you? I understand if not, it’s cool. I get it. I just got out of prison and you’re probably not big on dangerous geeky types.

That said here’s my stuff:
aim: yannibmba
yahoo: yannibmbr1
msn: yannibmbr
And you don’t gotta call or txt it, but my phone: 714.555-1212

Have a good’un.

Now I’m sure this message would have you think that there’s no way I could get a reply… Yet I did. Obviously this girl is a Sci-fi junkie, which is good because I am, too. But more importantly, being the second message, I chose to give her my number and IM contacts. I did this because I didn’t want to repeatedly message back and forth. I wanted to move things beyond the Inbox and onto IMs and phone calls. Yes, I consider IMs another step beyond messaging through a dating site. You get a better sense of a person based on how they respond to what you write on-the-fly. I also offered up my phone number and I kept it low pressure. This person ended up texting me and we texted back and forth a few times before I finally called, which is what I wanted all along.

With regard to online dating, this is the ideal flow I like to follow.

  • Avoid long, drawn out, back and forth messaging if possible. Keep it to about two or three messages before asking for a number.
  • Have a phone conversation with the person, or at the very least an IM convo.
  • Arrange a simple first date; coffee or a drink.
  • If all goes well then go on another date.

This flow is simple and helps ensure that neither of you are wasting the other person’s time. That’s the convenience of online dating; meeting people you might not ordinarily have the opportunity to meet and then quickly find out if there’s a spark. If not just move on to the next. Short and sweet, just like me mum. There’s always exceptions to these rules I’ve laid out and everyone has to work with what’s comfortable to them, but I find that this works well for me as well as some other people I have talked with. Try it out for yourself and see what your results are.

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Alex is the founder, creative director and managing editor at the Urban Dater. Alex also runs his own boutique marketing agency in Orange County, Ca: DigiSavvy. Among his treasured pursuits are bike rides with his girlfriend (don't be perverted, now!), hiking, watching the Portland Trailblazers and the LA Angels. Follow Alex: Twitter | LinkedIn

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  1. says

    Great advice as always Alex! I'd also add that you should show some awareness and respect for women's concerns about safety and privacy by writing something like "I'd really like to get to know each other better by talking on the phone. Would you prefer I call you or you call me?" The guys that write the "here's my number, call me!" emails are generally seen as the not-very-interested lazy guys.
    If you're a mensch and show your awareness and that you're actually trying to ask the woman what SHE wants…you'll get points and a good response. (At least from smart women looking for a nice guy.)
    .-= Bobbi Palmer´s last blog ..How to Make Friends With Rejection =-.

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