Dating in your 30s or Modern Anguish Pt 1

Morgan Hewitt
10 min readApr 1, 2022
Are we all clowns in this game I call dating in your 30s?

Disclaimer: Part of this originally formed an article for someone who asked me to write for their blog regarding dating from a male perspective. I cannot deny that this person is someone I matched with on Hinge prior and in the week before meeting she had asked me to contribute to her blog. Just so you’re all caught up, unfortunately I received the classic “just as friends” line post date and then subsequently all contact dried up so assumed my writing would never see the light of day… until now! So Amanda, if you ever read this, your loss is everyone else’s gain! :)

Second disclaimer: This is aimed at ALL 30 somethings who are dating or are thinking of it, I’ve edited the original feature so it’s not just focused on men.

If you’ve read any of my minuscule output on Medium so far you might gauge I’m a bit of a football (soccer) fan. Millwall FC are a club situated in South East London, they’re a bit naughty shall we say, but they have an interesting motto being “No one likes us, we don’t care” owing to their shenanigans off pitch in the last thirty years or so, highlighting them as an unpopular club to support compared to others in London.

You might think referencing a gnarled football club in South London to start a piece about dating in your 30s a bit off piste but bear with me…

The anecdote of “No one likes us, we don’t care” rings true, no one likes us 30 singletons it seems, that’s why we’re all here, but we do care… we care a lot, especially when the dating pool near evaporates before your very eyes the closer we edge to everyone’s favourite number… the magic 40.

It was after recently returning from New York for a 9 day break off the back of a couple of dates (one of which aforementioned) I got thinking of a few things:

  1. Dating in NY is nearly the same as it is in London.
  2. And more pertinently, why the hell is it so hard to date successfully in your 30s?

I have a few theories and I’ll cover these in a more philosophical article sometime in the near future, but ultimately what I want to achieve here is to help anyone reading this have a better dating experience by being as prepared as they can be.

Let’s not pretend dating and finding a proper partner is easy, and some bad news friend, you hit your 30s and it’s a shithouse of woe. It’s probably harder than a job interview, and it’s thoroughly frustrating to find a long-term partner. What I hope you’ll avoid is becoming bitter, as this leads to resentment and lulls in self-confidence — I should know because this has happened to me a number of times.

Rejection is never nice, but preparing yourself for dating and the pitfalls that come with it can ultimately lead to better experiences for you. The picture isn’t so bleak, there is much fun to be had, especially in a post-pandemic world where meeting new people should be a joy.

Ideally I’d love to change the dating scene, I’d love to say everyone will treat you like they would expect to be treated and honesty would be the number one go to trait for all involved but I’m not that naive. Nor am I a god.

However, I am a firm believer that if you can be honest and kind in your approach then eventually the good will out. You will find a way and you will have successful dates and who knows… maybe more which is why we’re all in it in the first place.

So, with the intro out of the way, let’s go to Part one -

Part one

Just so you know…

When I was in my mid to late 20s, adulthood felt like a distant speck on the horizon; parties were plentiful, booze and drugs flowed like… err… water, shallow friendship groups were in hot supply and lays were easy enough to come by.

Then in 2019, in the blink of an eye, I realised I was mid 30’s, still house sharing with multiple strangers, friends were disappearing quicker than my bank balance on a Friday night and I was continuing to bumble through life without a driver to keep myself on track.

By the end of the year, I made a decision to leave London and I moved back to my family home, but in the interim, and this is the important bit, just as I was leaving the city I started to date a girl who I met on Hinge (my go to dating app if you hadn’t noticed).

The move was supposed to be for a few months whilst I paid off a bit of debt I’d accrued (the funny thing is booze and drugs don’t decrease in price and neither does rent for some reason…), I never intended to move back to my home for 15 months, but some disease from China had other ideas…

The fledgling relationship sailed on partly through January, February and then March of 2020, just before the first U.K. lockdown, where it came to an end, me finishing it as I wasn’t 100% sure it was right.

It ended with a bit of a whimper, we both wrestled with the idea of keeping it going but the plague and my overall gut feeling didn’t really point to keeping it alive.

It was at this juncture, licking my wounds thinking i’d failed in life, that I became interested in why yet another relationship had gone south. I started reading article after article on Medium looking for potential answers into my psyche and the usual ‘5 reasons why you suck at dating but never realised’ kind of posts but it wasn’t until I came across one (I forget now the author, sorry) that referenced a book which changed the course of my life to now. As i’ve got you in the palm of my hand on a cliff hanger, let me move to my first major point of Modern Anguish Pt 1…

Know yourself

As we’re in our 30’s let’s assume we barely have any single friends left, so meeting friends of friends is not an option. I’m also willing to bet, given we’ve spent 2 years inside, social interaction with others in a public space is probably a bit of a challenge, so approaching that hunk at the coffee shop is too panic inducing right? Also, work relationships are cool but don’t always end well. So let’s go all in and focus our attention on online dating, whether that be websites or dating apps. Whilst some of you have at this point have rolled your eyes and stopped reading I hope the remainder of you find it of interest and useful.

Straight up and off the bat, before even begin thinking about downloading a dating app or creating that delightful profile with photos of you and a dog think very deeply about where you’re at.

What I mean is, look at my example above. Could you say, I, in my early 30s who was going out, getting wasted, then chatting shit around a kitchen table until the early hours of any given Saturday was in a good place? My answer to that is probably no.

So be brutal with yourself, maybe you’ve been recently hurt in a long term relationship and are getting ‘back to business’ by testing the water on the dating scene but are having little luck, or maybe you’re in your early 30’s and are now ‘serious’ about settling down and have an overly long winded checklist a person has to meet to even come close but every time you date someone they fall at the maybe the 3rd or 4th checkbox and are cast asunder?

Both of these are crass examples I appreciate but the sentiment is there. Look in the mirror and if you’re feeling depressed or something is “off” in life then it’s probably not a good time to date, and moreover seek some professional support.

Dating or a fledgling relationship should never “fill a hole” in your life, as it just can’t. I know, I tried.

If you’re still unsure about whether it’s time to date it’s cool to ask a close friend / family member their opinion on it if you have any doubts.

I also highly recommend reading the book ‘Deeper Dating’ by Dr Ken Page. This was the game changer I mentioned earlier.

In Deeper Dating, Page, at a high level, offers the reader a step by step process into unpacking inner desires but also highlighting behavioural patterns you adhere to which keep you single and wanting.

Yes, it’s quite hokey, and being British I had to place my cynicism by the door but I persevered and did the exercises recommended in the book and followed through to the end.

After the last relationship I had fell by the wayside, it was this book which opened my eyes to why I kept having short term relationships that went nowhere and what my attractions of deprivations (the bad people I’d go for) were versus positive traits I admire and should look for. It also helps you to grapple with the concept of vulnerability and honesty which many of us are scared to adopt in their lives.

If anything, the book is fantastic at highlighting the negative attraction patterns and is worth buying alone for that to help open your eyes and avoid going for / swiping on the Johnny-Come-Latelys of the world which litter your life with shit.

It also introduced me to the notion of therapy that I needed to seek additional, professional help to iron out and guide my hand, which I have from the summer of 2020 onwards to present day.

So if there’s any doubt in your mind about whether you should date or not, or your have some unresolved anxiety then maybe take it back to basics, sort yourself out and then and only then move forward with dating.

Know what you want

When I first downloaded Tinder back in 2013 I had no idea what I was doing. I thought the primary concern of the app, in those halcyon days, was for hooking up.

Between then and now I’ve downloaded the app and deleted it umpteen times through sheer frustration at either the nature of it all or just myself.

Let’s be frank here, I am not an enlightened guru, I am merely trying to navigate this shitshow of mid 30s dating along with you.

But the truth is, back then I didn’t know what I wanted. I craved sex yes. I think that was my intention, at its fundamental core. Still, I felt at the time, I wanted someone on my terms when I wanted them. Which in hindsight is pretty fucking selfish and sexist of me. Again, like we all are, I am a work in progress and was a younger man then.

Ultimately knowing what you want is in the same vein as being honest with your intentions. Going on dates with people who are serious about finding love when you’re just about finding lust is not fair on them and is very selfish of you.

Let’s take my New York dates for example, I used Hinge to match with some new people, I made it clear on my profile that I was in town for X amount of days. I got chatting with a number of great girls and I was very lucky to go on dates with a couple of them.

I had a fantastic time but I made it very clear I was there for a limited period and I wanted to hang out and see some cool neighbourhoods. In both instances I came away from the dates feeling unsure about what had just happened. At no time was it made clear that it was purely a plutonic thing and perhaps it should have been:

- Amanda acted like she had been shaping up for a potential romance and was disappointed this concept of ‘Hollywood romance’ hadn’t happened hence the drop off in communication post date.

- The second date kept in contact with me but made it clear she didn’t want a long distance relationship after spending the date with me.

In both instances lines were blurred despite my written warning on my profile that I was not going to stick around in New York City beyond the 9 days of my holiday. There are prime examples of what happens if just one party isn’t honest with their intentions and the space created in the aftermath of both instances here created unnecessary questions which I had to seek answers for. I wasted emotional effort in doing so.

So if you want ‘casual fun’ or just a friend to go running with then stump up, explain your intentions from start, make it clear in your written prompts or ‘about you’ sections of your profile.

The most important thing from this is not to waste other people’s time and emotions. When you get to your 30’s time is an important thing for a number of reasons, the number one being we’ve all had enough of time wasting, whether we experience that from friends or intimate relationships and let’s face it, we’ve all lost 2 years of our lives to Covid restrictions.

If you find yourself mentally flip flopping between camps of “wanting no strings sex” but maybe “wanting a cuddle buddy” then you are not ready to date. Figure what you want out first then come back to it. Don’t waste people’s time and don’t play with their emotions. Bottom line.

Conclusion

There you have the first part of the three part series ‘Dating in your 30s or Modern Anguish’. I hope it’s helped you consider the foundations of setting up before moving onto the exciting part of getting involved in the act of dating proper. I have no doubt that answering both questions above honestly, and if you need to work on aspects of yourself before indulging in dating, will help to make a massive change which will have positive consequences for you further down the line and also allow you to deal with the curveballs dating in your 30s will throw at you.

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Morgan Hewitt

Trying to make sense of this Rubik’s Cube world one twist at a time… Ex of UX design. Empath by nature. The rest is a history unread.