Dating After Divorce: How Hard Can It Be?

“We can either choose to be free and happy in the unknown or to be confined and suffer in the familiar.” ― Joseph Nguyen

We went to a friend’s house last week to see his cat. In case you didn’t know, I’m a very much a cat person and will always say yes when someone asks me to babysit their cat.

What started as playing with his beautiful white ragdoll cat turned into a heart-to-heart 2-hour conversation about his current dating life. I don’t have many friends who are divorced and willing to go back to dating right away, so I was very curious about his situation.

People say dating in your twenties (especially in the early twenties) is hard. Nothing new here. But how’s dating in your thirties/forties/fifties feel when you’re also divorced? How hard can it be?

I always imagined it’d be a lot harder; that’s because now you have some baggage from the previous relationship, but to my surprise, he said it’s actually much simpler. Since you’re now older, you already know what you want in a partner, or at least you know what you don’t want to repeat in your future relationship.

This is a big deal for those who are still in their twenties because most of the time, they don’t know what they can’t tolerate. You only find out after being in bad relationships. At least for me, that’s the case.

I didn’t know what “normal and healthy” behaviours looked like in a relationship until I hit my late twenties — early thirties. I didn’t know back then that it’s impossible to build a relationship with someone when your cup is empty.

I also didn’t know how your unresolved childhood trauma can literally fu*k your relationship over, and you don’t even realise it. You’d blame the other person because it’s the easiest thing to do. Then you’d run away and try to find a “better match” — only to realise you’re the problem.

(That’s the hardest truth — admitting that you’re the problem.)

All these take time to figure out, and I hate to say this, as awful as it feels being in a bad relationship, sometimes that’s the only way you can learn your lesson.

Though my friend said dating after divorce is still hard, it’s way less confusing. That’s good news, right? He also said he’s leaning towards emotional connection more than focusing only on the physical chemistry.

Well, hooking up is still a nice idea, but the chance of being in an exclusive relationship for the sake of a great time is very unlikely.

Another thing he mentioned that I think is interesting was how less desperate he was in trying to find a new partner. Instead of swiping on dating Apps like crazy and questioning whether or not he’s still lovable, he chose to stay busy by trying out different things and learn more about himself.

From travelling across Europe solo, joining a yacht community (which he admitted was very uncomfortable to do), to signing up for pilates class twice a week — he did it all with an open mind.

I honestly think that’s the best approach when it comes to dating in general. Remember those quotes that say “the more desperate, the less you’ll find love.” This is true on so many levels. Even if you end up finding someone, that relationship will very unlikely last long.

There are a couple of reasons why this happens: you’re in this vulnerable mental state where you feel like you need someone else to complete you. Instead of realising that this isn’t the case, you accept the first person who comes into your life — even if they only give you the bare minimum.

I know that severe loneliness can bring us to make a decision like this, but it’s worth reminding yourself that the damage can take years to repair. I’ve made mistakes in the past where I wish I had stayed single just a bit longer rather than dating the wrong guy (again).

Not only would dating the wrong person add unnecessary trauma, but it would also distract me from working on my existing and overwhelming childhood trauma. So if I could turn back time, I’d go with intentional dating over anything else.

No one says going back to the dating pool, especially after a divorce, is easy. But it shouldn’t be too complicated either. Of course, occasionally, you might feel like you’re running out of time.

Some people feel like their past relationship was such a waste of time that now, after the divorce, they want to build a new family with someone new as soon as possible. The clock is ticking.

This will eventually lead to desperation, and if they’re not careful, they might settle down with someone who isn’t right for them. My own mother has this pattern because she convinced herself she was ready, while in reality, she wasn’t. A decade later, she ended up with three failed marriages.

Now she dedicates her time to learn about herself more and stop seeking validation from men.

The whole point of me telling this story is to give you some perspectives that just because dating is hard, that doesn’t mean you should give up finding what you want.

If you ask yourself truthfully, excluding other people’s expectations of you and the “society standard”, you’ll have all the answers you need. While I’m not asking you to obsessively check every box in order to make sure they’re the right person and be very picky, I’m also encouraging you not to settle for less.

You’ve gone through so much in your past relationship. You’ve also learnt a lot along the way. So let’s make sure you don’t repeat the same mistake and relive those pains.

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