Yes, I Dated Before I Was Ready — Here’s What I Learned

One of the first things many of us get curious about after a divorce is dating.

Whether we initiated the divorce or not, there’s usually a little voice inside that wonders what it would be like to venture out into that mysterious world again.

I’ve sat across from people who were married for anywhere from eight to forty-five years. Those who initiated and those who had the choice made for them.

And what I’ve learned is this: age and circumstance don’t matter when it comes to the quiet question, “Is it too late for me?”
Again and again, the people I support have shown me that it’s not.

Short Term Or Lasting - They Still Matter

Even when we suspect it’s too soon, many of us leap into something new after divorce, hoping it will ease the ache or fill the enormous void that is left when our partner is gone.

I took those leaps myself. It didn’t unfold how I hoped it would, but it taught me a lot.

Coaching people who are exploring the dating world after divorce has reminded me of my own early rebounds. They helped me survive, but not without cost. A bit like emotional duct tape. A quick fix that bought me time, but also left marks that took longer to heal.

I had two significant rebounds.
One was about six months after my marriage ended.
The next one started two years later, once that first one finally came to an end (after a few breakups and reconciliations).

It was messy. It was painful. It was confusing.
And yet, I gained a lot from those experiences.

Did I know who I was or what I truly wanted?
Not in the slightest.

Did it matter?
Not really. I wasn’t chasing a soulmate. I just needed to know if I could connect with someone as myself again, not the version of me that had gone numb in the marriage.

What My Rebound Relationships Taught Me

The first was a classic rebound. We both knew it. He was recently separated from his wife of ten years. I told him up front I wasn’t looking for anything serious.

I didn’t realise how much pain I was in at the time. It’s not until I look back and remember that ache, that confused panic, the terror that would show up and annihilate me.

That first rebound got me through some of the worst lonely weekends.
Those ones where the kids were with their dad, and I was home alone, having an existential crisis on the regular.

I ended that relationship without much emotional upheaval. It served a purpose for both of us. I’m not really sure how he felt about it, to be honest. He tried to stay in contact, but eventually I stopped replying to his messages.  I guess that’s the complicated world of dating after divorce.

My second relationship started a couple of months after that one ended.

This time, I thought I knew what I wanted.
I was convinced I was ready for something real.
Little did I know.

I moved too quickly because the physical attraction was so strong.
We were both freshly out of our marriages, both raising young kids, and trying to build a blended family before either of us had truly healed.

I put him on a pedestal and twisted myself into a pretzel trying to be the perfect partner. I was hellbent on getting it right this time around, and I ignored many, many red flags. 

This relationship was not light-hearted, and it caused me a lot of heartache and chaos that I really didn’t need in my life at the time.

I could beat myself up for this. I spent quite a few years after a very painful breakup doing just that. But I slowly worked through it. I forgave myself for my naivety and made the decision to look for lessons instead of self-blame. 

Although neither of those situations was ideal, there’s no doubt that I learned a lot from each connection and had a lot of great times as well. 

Here are some of the most important lessons I took from those early rebounds:

• Old fears around trust and infidelity don’t just disappear. They show up in new ways unless I name and work with them.

• I need space inside a relationship. I can’t be in someone’s pocket. I need alone time to feel sane, creative, and spiritually grounded.

• I’m not ready (and may never be ready) to step into a parenting role with someone else’s kids.

• Some wounds, like fear of abandonment, don’t heal just because you’re in a relationship.

• I still had a pattern of over-giving and under-asking. I needed to learn how to speak up when I wasn’t okay.

• Physical intimacy matters to me. It’s not shallow, it’s a core part of how I feel connected and alive.

• I want to feel like I matter. Not just fitted in around someone else’s life.

• My sense of worth still wobbled. I was seeking validation instead of knowing I was already enough.

• The deepest healing work can’t be outsourced. I had to face myself, on my own, to really heal. 

Some of those lessons hurt like hell. But they taught me what no book ever could. I don’t do that stuff anymore; losing myself, ignoring red flags, twisting into knots to be liked.

These days, I’m good on my own. I like my space. I like knowing who I am. And I know that when I’m ready to date again, it’ll come from that place. 

Not from fear or loneliness.

The Challenges We All Face

While the lessons above were very specific to my unique divorce journey, there are some themes we’ll all face when we choose to dip the proverbial toe into the dating pool again.

If you’re exploring dating yourself, some of these might sound familiar:

• Companionship can’t fill the hole of grief, and that’s okay.

• Rushing into something often comes from not knowing how to sit with the void

• Even when a relationship doesn’t last, it still counts. It still teaches.

• Chemistry doesn’t always mean compatibility.

• Emotional intensity isn’t the same as emotional safety.

• Craving closeness is natural, but you might not yet be ready for true emotional intimacy.

• Performing to be “likable” instead of being honest wastes a heap of time.

• Clear boundaries with yourself are just as important as boundaries with other people.

There’s no right or wrong way to do it

There’s a reason rebound relationships have their own name.
It’s rare for someone to stay completely single for years after the end of a significant relationship.

Taking time alone might be the wisest path after divorce, but most of us don’t start there. So let’s give ourselves permission to explore if that’s what we feel like we need. No shame and no judgment.

Just humans, learning lessons as we go.
Isn’t that what life’s about, really?

Whether you’re dipping a toe or in the middle of a new connection, take solace in the fact that nobody has a perfect roadmap.

But if you stay curious, honest, and connected to yourself, the lessons will come, and they’ll be exactly the ones you need.

Until next time,

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