How to date at 38…or possibly how not to.


“Make sure you include a full body photo so they can see you’re not carrying a few extra kilos.”

After an interesting tearoom discussion with two lovely work colleagues about dating in the modern world, I found myself reflecting on life back in the dating scene. That fact that I call it a scene shows that I’m rapidly approaching my George Clooney salt and pepper years. I mean, do scenes actually exist anymore, and if they do can I join the Drinking Tea and Eating Chocolate While Watching Buffy re-runs Scene?

Smashing up against my late thirties I find myself trying to figure out what the fuck it means to actually date someone. While 38 is by no means old, it certainly isn’t young especially in a world where the primary form of dating seems to require apps, very good Wi-Fi and apparently social group dating (whatever that fuck that is Tinder).

In days gone by, when I previously visited single land, dating apps were dating websites, and the taboo that came with it ensured you never actually mentioned to anyone that you met online; it was either at a party, through a mutual friend, or my personal favourite, at a wedding. But times have changed, as they do, significantly in a short space of time, making meeting new people as easy as a swipe to the right. When my passport to single land was first approved, the first thing I did after getting significantly drunk on Christmas Day, was hit up Tinder and swipe right with mates while drinking heavily.

Within the first hour I was chatting with a girl who suggested that I bring a friend to her house for a late night drink with her and her housemate – on baby Jesus’ birthday? At the same time I started a pleasant conversation with a nice girl that eventually culminated in an actual date. We met at the beach, grabbed take away coffee and had a nice three-hour conversation under a beautiful summer sun, strolling the familiar path between Henley and Grange, then back again with the occasional stop on the sand. There was nice conversation, laughter, and a mutual understanding that somehow in the chaos of the universe we may be having a great online experience. Could this not be the perfect rebound? A few days later another date ensued with similar enjoyment – things were looking up.

Third date was excellent which included a delicious dinner with a few cheeky wines and it no longer felt like I was doing this weird thing called dating, but just having a pleasant conversation over dinner.

I had heard stories (or possibly urban myths) of people who had come out of long term relationships and straight away bumped into their one and only. All the signs were pointing to such an experience. Good conversation, pretty girl, intelligent, can hold a conversation without various pit stops to her check her phone. I was preparing myself for impending bliss.

I rang the following day (yes an actual phone call, I like to kick it old school) to say how much I enjoyed her company and was told that she was terribly sorry but she was actually seeing someone else; apparently another Tinder match had been working a quicker online magic than I. Beaten at the finish line – or perhaps I wasn’t even in the race? Hang on a minute, is dating like managing investments? Should a single person have a variety of investment portfolios so that if one crashes there are still other options? Just how many fingers in how many pies is one supposed to have to successfully navigate the dating “scene”? I couldn’t think of anything more stressful.

So while my immediate response was to feel all kinds of disappointment (our overseas holiday and dinner with friends would’ve been amazing) I found myself laughing at the experience and my attempt to find to what possibly could be a short term solution to my newly found singledom. Apparently online dating is not only about impressing the person you’re with, but also competing with all the other dates she/he has been on the day before…and the following day.

For every negative online dating story (of which there are many) there are some where the stars align, and the universe smiles upon you to deliver a happily ever after. I’ve seen a few of these, and let me tell you its looks pretty fucking amazing; a real thing of beauty. Amazing enough to want to persevere for that special swipe right.

The prevalence of online dating platforms like Tinder, Plenty of Fish, RSVP and E Harmony (just to name a few), are merely a representation of how difficult it can be to meet people not just for a relationship, but to increase networks and make friends. Sure you can join a class, or a community group but these options can often take a long time and god dammit when winter is coming you want that Game of Thrones, wine, blanket and couch option now damn it.

Is our greatest challenge being the best version of ourselves when unplugged from the Matrix? In a world dominated by online profiles, are we not confident enough to be who ever the fuck we are in the flesh for the whole world to see? Meeting people in all reality is not that hard and evidenced by any time spent overseas where talking to strangers and going on adventures is commonplace. So should we be tourists in our own cities?

[For a great read on drinking alone in bars and the art of meeting new people wander over HERE, but be sure to come back].

But dating at 38 has become simultaneously easier and harder all at the same time. While asking a girl out the old fashioned way (to her face using actual words, a smile, eye contact and no emoticons) will never be easy…

…at this point in the article I am tempted to tell my Year 6 Rebecca Wauchope love of my life story, but that’s another post entirely…

…there are other elements that are suddenly a lot easier; namely the comfort of knowing who you are and the key to compatiblity. Additional years also come with a deep understanding that life is about seasons, and even though some things come to an end there are always new beginnings; leaves have to fall for flowers to bloom.

Another advantage of the added years is appreciating that life can’t really be planned but only prepared for. Change is our only constant, which now brings with it a deep excitement for the opening of wonderful things never previously considered; there’s no need to fear new chapters.

I’ve seen a few changes in seasons in my time and my fare share of endings and beginnings and no matter how many full body photos I try to find that show me less Dad-bodish, after all these years there still is no substitute for being exactly who the fuck you are.



5 thoughts on “How to date at 38…or possibly how not to.

  1. This is great, Andrew. In some ways it [sadly], makes me miss the single/dating life. The excitement, the potential, the ups and downs, the anticipation. It’s all good! I have every faith that another Ms Right will appear soon enough, and in the meantime, enjoy the ride! x


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