5 Steps for Re-Entering the Dating Pool

In recent weeks, it has been brought to my attention that these articles from the perspective of single Dad (Me), could be misleading a few people. With that being said, I figured now’s the time to clear this up.  I am the father of two wonderful little ladies, this makes me a Dad.  Many years ago, the relationship that begat these children dissolved, so I received the title of ‘Single Dad.’  I was then faced with a choice, do I stay a single person for the remainder of my life? or, do I search for the right woman some more? Clearly, I chose the latter or the start of this article would make no sense.

Here are the 5 steps I went through re-entering the dating pool.

1. Into the Pool

Each of us has sat in a hot tub, relaxing and enjoying the peace of the soothing waters and jets.  After awhile, that tempting looking swimming pool just a few feet away looks wonderful.  Each of us has our own preferred method of making that transition — I always chose to walk over to the diving board, climb up as high as I could and jump head first.  Be honest, how many of you just had the cold chill run through you thinking of the sensation involved in that cold plunge? Well, my first year or so was one long plunge.  The shock of the re-entry and life in general as a single and very insecure Dad was astounding.  I was a menace to myself and others.  I was not setting a good example to my children on how to treat woman — I was not in a good head space to find any success at picking up, meeting or effectively pursuing women.  I was a train wreck, worse yet a train wreck that found his only outlet was work or beer.  My unauthorized OT was stopped and I found that the Shark’s Club had comfortable stools. In return for my money, they not only provided food and beer, but a new body shape — let’s just say I looked pregnant.  I immediately set about removing the new belly I had begun to grow.  Clearly, I needed to rethink this head-first thing.  This stage also marked my first foray into online dating — the love/hate relationship with that medium continued for quite some time.


Susanne Nilson, Flickr

Susanne Nilson, Flickr


2. Drink Some Coffee, Walk Around

There is an old Bill Cosby bit about waiting for a toddler to talk to her grandparents on the phone. After several hours, Bill takes the phone back and says “Mom? It’s ok, drink some coffee walk around.” Really that statement contains the key to properly getting into the dating pool.  Take the time to wait for the payoff, much like with a toddler’s phone call, the payoff may not be fantastic right away but it will get better.  I also found that those two things are a much better start than drinks and liquor-enhanced lust.  It was about this I time hit on the connection between my dating life and how my children will be affected by it.  It scared me to think that someone will one day treat my daughter the way I was treating these women.  This was the second major adjustment, not easy and I won’t say I was definitely not perfect from then out but I did have a better grip on things from then on.


Rosefirerising, Flickr

Rosefirerising, Flickr


3. Squeeze the Melons

If you go grocery shopping, you can’t just pick the first melon on the pile.  Inspect it, check for bruises and defects, then give it a squeeze — is it as solid as it looks? If yes, buy it take it home and eat it. Same with dating… hmmm… maybe not as good an analogy to make there, but enjoy the laugh.  Here’s where online dating really messed with me: too many people lie.  This fish crawled on land a few times before jumping back in the pond.  I had to learn to not go after every woman who showed interest. I was not the mess I thought myself to be, so turning down a few was necessary. Think of it like a server asking if you want more coffee, a polite “No thanks, I’m done here” is ok. If that gets a bad reaction, then you probably did the right thing. It was in this stage I realized while dating a single mother that we had progressed to a stage where we were not dating. I with my two kids, had begun dating her and her two kids. This relationship suddenly vanished as we both seemed to sense that. Life changing epiphany #2.


4. Unpack Your Bags

We all have our baggage.  Single parents and divorcés tend to have a ridiculous amount of carry-on luggage that we eventually just put down once we understand we do not need the contents.  I found a girl that I had started to unpack with and I began to really tackle what I think is a major hold back for me due to what I consider a great failure — being a Step Dad.  My first tour of Step Dad duty I feel was horrible —  I must confess, I am largely ashamed of my performance. It’s not that I was overly cruel or anything, just young and unprepared and I hope one day to find a way to make up for it.  Now then to my point, I started to leave that bag behind and was really enjoying the feeling of that role again. Sadly, that relationship ended up with a wall between the adults and it too failed.  It took almost a year before I found the next real worthwhile person. I had grown annoyed with ‘offline’ dating and replied to a message sent to me, a rare occurrence indeed. There was a coffee, then another, Christmas party, family get togethers, New Year’s Eve –20-months-later, we live under one roof with 4 children, 3 cats, 1 gecko and cows everywhere.  I had to unpack so much baggage it has been exhausting and scary, but it has been worthwhile, despite not being a story free of flaws.


Ilovebutter, flickr

Ilovebutter, flickr


5. If You Like it, Put a Ring on it 

Well after all that, there is only one place to go…  right? The final frontier, boldly go where….ok, nearly everyone has or will go.  I’m not there yet, but I don’t feel the title of Single Dad works on me these days, just Dad. This step is looming on the horizon and you my friends have a seat for the ride.