From the BLOG, 2015:

Internet dating in the city~

Hello, my name is Annie O’Leary and I am an internet dater.

I am inspired to write this blog in an effort to streamline the efforts of the millions singles on line at this very moment looking for true love. As a bonus, I hope to provide comic relief to your process by sharing a few choice details of my 200+ first dates.

I invite you to read about my follies and those of my friends while navigating the internet dating jungle…. Ask questions, get advice, share your amusing experience… something similar has no doubt gone down in our camp. I will try to sift through the antics and get to a solid take away message from our collective experience, so we can all sharpen our skills.

As for me, I am pretty self-explanatory in my profile. I am honest about myself and what I do, where I live (a city girl), likes and dislikes, and most importantly, what I actually look like. Isn’t the point of being on one of these sites to actually meet someone, in person? Well, that has been my point anyway…

  • Date log - June 7, 2015

    If you are blissfully unaware of this, I am sorry to have to inform you that it’s your photo that gets someone to look at your profile, not your witty headline. So, I urge you, save time for everyone, be honest with yourself and others regarding your pictures. We will talk much more about the important forensics to be ascertained by profile pictures later, but for now let me tell you what happened to me, early on, when I was less adept at profile interpretation and its many clues… my naivety it this arena led me to one of the most memorable internet dating experiences called:

    A date with Dan: a story of heartache and high-tops In Dan’s profile there was just one photo, taken from about 6 feet away, he was smiling brightly wearing dark glasses on a sunny day…. I wasn’t adept enough to realize his one picture contained red flags, the fact that it was, just one picture with glasses on. He said he was an entrepreneur, had never been married, had no children and lived just outside of the city… Aside from the suburb part, very in line with what I’m looking for. When I showed up at a bar in the very hip, Pearl District of Portland at 9 on Thursday, Dan stood up, “Annie!!??” In my head, I responded, “No, my name is Nancy”, and I kept walking... most of us have had the impulse to do this at one time or another. In actuality, because I’m a dead ringer for my pictures, I smiled sweetly, sat down and ordered a Diet Coke. You should know this about me, if I order a Diet Coke at 9pm on a Thursday, I won’t be staying long. Dan’s attire was not what I was expecting for a Portland Hipster. He was wearing his original football jersey from high school, he was almost 40. How do I know? Well not only because it was red, faded and what they wore in 1989, but also because it he told me. Proudly. He paired that, tucked in, with a pair of high waisted, acid washed black jeans that bunched around the ankles at his high-top Reeboks. The all white, velcro at the top kind. This is what he came with, out of his entire wardrobe, to impress a girl. And then there were his eyes… I am not one to shame someone for their looks, but in this particular case, I did feel slightly manipulated. You know when someone has a wandering eye, you are supposed to look at the stationary eye, right? What if someone has TWO wandering eyes? Yes, it’s true, like marbles on a roulette wheel. Now I understand the dark glasses in the solo picture. While swilling my diet coke, I learned that he was not actually an entrepreneur in the cannabis industry as stated on his profile, he was a deep-sea fisherman that grows marijuana for this personal use, has two ex-wives, three sons (two moms), and is suffering a deep depression due to his latest wife’s infidelity with the contractor hired to renovate her hair salon. He punctuated his story by bringing it back to me, suggesting that if I “needed to get laid, you should simply hire a contractor to work on your house.” Thank you, Dan, I hadn’t yet considered that strategy. Today’s takeaway: Dishonesty in a profile (spouse(s), kids, profession) is something that we, the daters, have no control over, so in this case, I am off the hook for his dishonesty in order to better adhere to what I was looking for. Going forward however, I now require at least two pictures, without dark glasses (pictures taken in the bathroom mirror do NOT count), and, if detectable, I make sure there is less than two elapsed decades in fashion. Worthy of mentioning here was Dan’s emotional readiness to date after a relationship ending event. It is true that talking to someone can be extremely therapeutic in an effort to process what’s happened, and that listener should be a therapist, not a stranger from the internet. So, be sure you’ve adequately ‘unpacked your baggage’ rather than expecting someone new to carry it.

  • Date log - June 12, 2015-

    Today’s topic is delicacy, or perhaps, ‘not revealing how incredibly desperate you are in your message to someone that has perked your interest’. This entry was inspired by a couple recent messages, both were a turn off due to complete lack of subtly, nuance or intrigue.

    The first one, from a guy claiming to be a driven, solid professional. Perhaps he is, in addition, he is solidly desperate. SUPERCYCLIST32 writes this, and only this:

    “all I want is a good connection.

    I am a hard-working professional.

    I work hard, play hard and love life.

    A little frustrated no one will take me seriously and contact me back!!!

    Let’s start a conversation!!!?”

    My answer: no.

    Does SUPERCYCLIST really think I am inspired to have a conversation with him to appease his frustration? Well, I’m not. When you receive a message with this type of tone, I urge you not to respond….if you do, you may find yourself explaining the obvious, indefinitely… yes, of course you want a good connection Sir, we all do… is that an actual request?? The other, equally devoid of subtlety, in a manner I refer to as ‘sipping from the complimentary fire hose’… this arrived from PRICERIGHT_RC: “Hello beautiful lady, all I can say is WOW!!! If your heart is not already taken, I would like to apply for the job!!! Just so you know I would like to jump the line of guys waiting and go to the head of the class. Note: FYI: I only need one chance to get to know you. If I can’t win you over with my charm and or make you laugh while putting a huge smile on your face, then at least I would have spent some time with “Miss West Coast”!!”Over. Zealous. I don’t believe RC realizes that his clearly recycled intro message is having the opposite of its intended effect and perhaps scaring off the ladies. Delicacy, look it up RC. Then, perhaps use it when attempting to flatter.

    Today’s takeaway: when sending an intro message, keep it “light and breezy”, that’s right, light and breezy. Nothing more. Abandon overtones and/or undertones of desperation, embrace delicacy.

  • Up next: Facetime vs. Fantasyland, how too much texting can lead to premature expectations. Soon to come: How to discern whether he wants to meet you, or he’s simply a “collector”.