The Moment When You Realize it’s Time for Online Dating

By: Kevin Murray |

5831509222_ec29deaaaf_zImage via Instant Vantage on Flickr.

Everyone remembers that moment when they realized it was time for online dating. For many singles that moment is after a long lonely holiday season, where you’re reminded how all of your friends seem to be entrenched  in their 5 year plan while your spinning your tires in the mud – looking for someone to come dig you out.  Some of us go to online dating when we’re young, others make the move after 30 years of marriage that ends in divorce. All of us take different paths, but our goals for the most part are the same – we’re looking for someone to spend the rest of our lives with. However, my path to online dating was a little different. I more so needed to learn about myself, we all start somewhere. Here’s the story of my beginning.

(This was my original default pic from 2002. What you can’t see is me holding the family Bichon Frise. Horrible idea.)

The year was 2002, I was 22 years-old and hadn’t been single since the age of 18. While most guys my age spent their late teen years frolicking around college campuses knee deep in coeds, I was in a committed relationship playing house – the single scene was entirely new to me.  I figured being single was going to be easy. You see a girl at bar – she makes eye contact with you – you both smile and then go over and buy her a drink right?

Around this time in my life, my buddies and I frequently went to Providence, RI to this bar called The Fish Company (the 3rd review down on this link is spot on. I forgot it had a stripper pole, classy).  It was a typical loud, dark bar with a dance floor, DJ and also a seated area of to the side to just hangout and chat. We happened to come here a few weeks in a row and there was this particular cocktail waitress I couldn’t take my eyes off of.  She was about 5’7, tan, blue eyes, long black hair and the body of a swimsuit model. She was walking around taking orders, passing by my group of friends a few times. By the fifth go round I couldn’t take it anymore.

I leaned over to my cousin Joe said, “hey, I’m gonna go talk to that waitress.”  To which he replied, “yeah dude, no way you do it.  You’re going to puss out big time.”  I told Joey to fuck off.  But, the longer I stood there more I realized he was probably right.  There’s no way this chick is going to be interested in me anyway.  My cousin continuously called me a pussy every ten minutes that passed in which I didn’t make a move.  So just before last call I walked over to her.

My heart was practically beating out of my chest as I approached, my hands were shaking and there was no plan as to what was going to be said – every step I took toward her increased the crippling anxiety I felt.  I stopped right next to her just as she was finishing up with a customer.  She looks at me (could barely get the words out) – was frozen for a full two seconds.  “Hey, do you want to grab dinner sometime?” I blabbed. She goes,  “um… sorry… but, I have a boyfriend.”  Like a little bitch, I stood there and proceeded to ask her about her relationship.  Not only did I crash and burn, I made myself look like a complete idiot.

[vc_row][vc_column][vc_column_text][/vc_column_text][/vc_column][/vc_row][vc_row][vc_column width=”1/1″][vc_video link=”″][/vc_column][/vc_row]

I walked back over to my cousin shaking my head – he smirks, “how did it go?”  I paused for a few seconds to find my balls that I had dropped at the scene of the crime and said,  “dude,  I have no friggin clue what the hell I’m doing. I’m 22 years-old, been single for 5 months and I have no idea how to talk to a woman that I just met.” Joe replies, “well, at least you went over there.”  Nice bro, thanks for the support.

As we drove home from the bar I was thinking, this being single thing is complicated.  I kept asking myself the same questions over and over again.  Why do guys always have to make the first move? What do I even say to a girl when I first meet her?  How do I know when to a girl is interested in me?  Do girls even find me attractive? My head was spinning.  Being a single trying to get into the dating game with little experience is scary.  There was one final question,  “is there anyway I can practice going on dates to figure out what the hell I’m doing?” To my surprise, the answer to that question was yes. The next day I signed up for –  eventually, I would find answers to all my questions (and a LOT more).