Why Dating is so Difficult in Your 40’s

In the last several months, I’ve made a conscious effort to put myself out there to broaden my peripheral view on life. I not only feel a boost in my self-esteem, but I also feel that I’m socially more comfortable in my own skin than ever before. I’ve attended a number of social functions where I knew very few to no one at all. I’ve gone to business seminars and conferences that I normally would have turned down, and I even went on a number of dates just for the hell of it.

A dear friend once told me that going on dates is like going for a series of job interviews: you gain practice and experience hoping someday for that perfect match. As it stands right now, I remain unemployed.

I talk about dating with a number of my friends ranging in age from 26 to 56 and consistently, there’s one common denominator: Dating is hard! Let me rephrase that…dating when you get older gets freaking difficult and almost feels impossible at times.

Here’s my take on why dating can be difficult in your 40’s

Your Big Circle of Friends has become a Small Dot.

As I age, I get very comfortable with my own circle of friends. It’s like that comfy cotton shirt you’re not willing to part ways with because it’s served you well for decades (yes, I have one of those shirts) and have no reason to part ways with. When our circle of friends is already a tight knit group since the dawn of time, it can be difficult to expand that circle. But when that circle of friends begin to have lives of their own (ie starting new families, moving or changing jobs), that big circle of friends can become really small, like a dot. And the bustling social life that once was, has now dissolved to annual Christmas gatherings and the odd birthday party.



History Does Not Repeat Itself

Expanding on point #1, you and your friends have a long history together: You went to elementary school with them, or you saw them through their divorce. You were their best man at their weddings or you traveled with them and took a ton of photographs together. With years and years of history together, meeting new people who already have their circle of friends is like going back to the starting line in a game of chutes and ladders. It can feel exhausting to start new memories from scratch, especially when you have perfectly good ones with your own circle (or dot) already.



“No Matches Found. Please adjust your Filters.”

“She’s got to be taller than 5’1, relatively fit, isn’t allergic to any types of food, likes kids, enjoys watching basketball, reading and hiking. She has to be mentally fit and isn’t afraid to be silly. She’s got to like sappy romantic movies such as La La Land and Before Sunset. She’s got a killer smile, beautiful eyes and isn’t materialistic. She has an opinion on most things, can call me out on my shit and can quote Louise Hay. Oh, and she’s got to LOVE cats.”

Yes, as I’ve become older, I layer on more and more filters on what a good match for me would be. I sometimes wonder whether I’m subconsciously layering on these filters to self-sabotage any chance of success because I’m deep down terrified of dating again (hmm, quite possibly).

But at the end of the day, after every date I’ve been on, I just don’t feel connected and attracted despite all being really nice people. It feels like the uninspiring sequels to a great first movie. I wonder also if I’m just mirroring my own lack of inspiration and enthusiasm.



“Hi, my name is Hermit the Frog.”

It wasn’t too long ago that my self-esteem was lower than Barry White’s voice saying the word gingivitis on the David Letterman Show back in the 90’s. What this translated to was a very comfortable adult life living in solitude, sprinkled with the occasional social function. To this day, I very much enjoy the quietness of my own home and when my teenage son comes over from time to time, I already consider that a loud family gathering. I’m sure much of my preference to a relatively quiet lifestyle has to do with the noise triggers from my childhood. Loud voices and heavy chatter usually meant an argument, fight  or some form of abuse would ensue while growing up in the Lee household. I feel this has somewhat crippled my social skills and made me prefer talking to a volleyball than a real live person at times.



Online Dating is the same as going Shoe Shopping…

…you try on a bunch of pairs, but never commit to buying any of them.

I’ve found online dating to be quite the experience and maybe it’s a more efficient way of meeting new people remotely, but connections can be few and far between. This goes both ways, but there’s just far too many people to choose from, swiping left and right and when matches finally turn up, conversations are as short and shallow as “hi” which fizzles out because the prospect of another pops up. Sure, it can be mildly entertaining to flip through and get the odd social approval when your profiles match and light up in the middle of the night. But the temporary high droops down faster than taking a cold shower.



We are Creatures of Habit.

With our daily routines, who has time to date? I go to the gym every weekday morning at 5 am because it’s fun, healthy and it starts my day on the right foot. This means that I’d prefer to be in bed relatively early (or as my friend Tosh once said, I turn back into a pumpkin by 9 pm). I go to work immediately after and come home to unwind from busy days at the office. Saturday mornings, you can find me at a local coffee shop in PoCo either reading the paper, jotting down ideas in my journal for my next blog or podcast while sipping on a cup of coffee sprinkled with sweetener and a splash of skim milk. I sometimes add a hike in the afternoon or get together with friends for a meal, movie and dessert. I typically play basketball with my teenage son on Sundays because it’s fun for the both of us and a great bonding time.

Somewhere in between, I pick up groceries, tidy up the home, play with the cat, prepare lunch for the work week and do my laundry (ughhh, the never ending lauuundry…) The other night after work, I went out for a get-together with my coworkers. I got home by 9 pm and I completely felt discombobulated because my routine was thrown off. When did I become so inflexible? Maybe I need to take up yoga. Nah, no time.



At the end of the day, my personal growth and mental health needs to be my primary focus which includes practicing what I’ve learned over the years about mindfulness and establishing a better sense of self-worth than I ever did before. Everything else from new friendships, relationships, business opportunities and prospects is all gravy that can run parallel to the work that I need to apply on myself. And I’m content with that notion which means that I will continue with my mantra of broadening my peripheral view and saying yes more often to opportunities big and small. Each opportunity pursued is a learning experience to practice my speaking skills, to apply mindful behaviors and establish healthier beliefs in myself and in others.

I once read a quote that said:

If you’re looking for love, chances are you’ll have a hard time finding it. Instead, focus on yourself, your growth and pursuing your passions and Love will eventually take its course when all is aligned.

I think back to that beautiful quote every now and then because it reminds me of the work I still need to put in every day on improving myself, my self-awareness and my mental health to become the great man that I aspire to be should the right person come along.

Jason Lee, Author of Living with the Dragon.

Published by Jason Lee, Author

There’s something greater to be learned in our journey otherwise life would just be too predictable and I’m not quite willing to accept that!

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