Starting over after a breakup or an extended period of not dating can be incredibly daunting.
How long is it going to take to meet somebody? Is it a big, bad, scary world out there? What if I find it really difficult to cope with dating or do the wrong things? You can end up feeling incredibly panicky, frozen in indecision and anxiety.
When it comes to knowing if you’re ready to date, I recommend the Goldilocks approach: finding the middle ground between bouncing straight into dating with no real reflection or healing and not dating for ages because you’re ruminating or essentially in emotional purgatory.
Why Timing Alone Doesn’t Tell You Anything
Leave it too short and you’re likely escaping yourself, hoping that immersing yourself in someone else will rid you of your buried feelings or help you get over your ex or escape something else you’re avoiding. Don’t assume that because your relationship was, for example, three months, you ‘should’ be over it within one (that whole third-of-the-time rule of thumb that used to get bandied around a lot). What occurred in the relationship and how you treat yourself post-breakup or disappointment impact recovery time.
Leave it too long, though, and that comes with its own problems. It’s not “too long” if you made a conscious, empowered choice. It is “too long” if that period’s based on beating yourself up, building walls instead of boundaries, and avoiding vulnerability. This starves you out emotionally and makes dating feel destabilising.
When you finally date again or catch feelings, it’s like having a meal after several months without one. You think it’s ‘amazing’, but everything is exaggerated and distorted. It can feel ‘do or die’, like your sense of self will collapse if this doesn’t work out.
What Actually Matters When You’re Thinking About Dating Again
At that middle ground, how do you know where you’re at? Here’s what matters.
1. Knowing Yourself
Do you understand your values—what you need, expect, and want to live happily and authentically?
When you have some certainty about who you are, you don’t feel panicky about what’s out there. You know what you’re about.
People who don’t know themselves wake up knee-deep in relationships thinking, “What the hell is going on here?” They’re crazy about someone, but their needs aren’t being met. They don’t have as much in common as they thought.
Knowing yourself is also about knowing your intentions—your ‘why’—including where you’re bullshitting yourself. You go into dating for the right reasons and can spot signs you’re getting carried away or are out of integrity.
2. Trusting Yourself
There’s no point in dating if you don’t have faith in yourself. Self-trust is what allows you to trust others from a healthy place.
People who lack self-trust have their guard up, braced for pain, or go into dating looking for somebody to tell them who they are, immediately putting them on a pedestal. Having walls up creates a self-fulfilling prophecy. Outsourcing trust is like jumping into things blindfolded and with your hands tied.
Trust improves with practice and gaining discernment, but that’s tricky if you ignore, dismiss, and override your feelings, thoughts, and needs.
A good gauge of self-trust: the willingness to back and listen to yourself, even when what’s coming up is uncomfortable.
3. Being Present-Based
We all daydream, anticipate the future, and sometimes slip into the past. When we spend too much bandwidth replaying old relationships, trying to right the wrongs of the past, or fantasising, we’re not present—which is precisely what dating requires.
Here’s the test: if you came across something that’s previously been a trigger or blind spot, would you react differently?
Clients say, “I’m ready to date again!” They get on the apps, start talking to someone who mentions the future, and immediately picture their whole life together. Or they feel destabilised by dating, as if their self-esteem is tied to strangers. They’d got to a good place with self-care, but suddenly that goes out the window at the first whiff of romantic interest.
You’ll know you’re in a good place when you sidestep the trigger by responding differently. You talk yourself through it and ground yourself in reality: “Hold on. Let’s keep my feet on the ground. I don’t really know this person yet. Let’s just enjoy it for what it is right now.” You’re mindful of your blind spots.
4. Taking Care of Yourself
Many people see dating as a way of outsourcing their self-care and self-esteem. That’s too much to put on randos or a new relationship.
Relationships are amazing when they’re mutual and can honour the separateness—we each know where we end and the other begins.
Again, know your ‘why’. Dating because you want to and you’re already happy with your life? Great. That ensures you treat yourself with love, care, trust, and respect.
But if you see the apps or a date as your salvation, you’re already hurting yourself. Instead of taking care, you’re abandoning yourself for what you think dating can provide. You put the person on a pedestal, creating immediate imbalance and codependency—which isn’t the same as attraction or love. When you can take care of yourself in and out of a relationship, you are empowered.
What I Know Now
After 20 years of this work, I know dating readiness isn’t about how long it’s been since your last relationship ended. It’s about whether you’ve done the inner work to understand your part in why that relationship didn’t work or why you approached relationships and yourself in a painful way. Not to blame yourself, but to recognise your patterns and make different choices.
The people who struggle most aren’t the ones who waited “too long” or jumped in “too soon”—it’s what that time represented. They never asked: What was I avoiding by staying in that relationship? What am I trying to avoid by rushing into a new one? What was I avoiding by beating myself up or pining for so long?
Those questions tell you if you’re ready, not the calendar.If you have a good sense of who you are, you can trust yourself, are mindful and can take care of yourself, give dating a shot. There are no guarantees, of course. But you’ll be able to get a sense of whether something’s working for you. You’re in a much better place to find a relationship that’s actually befitting of you. Not sure where you’re at but want to date? Be prepared to listen to yourself and learn as you go. Be willing to opt out when needed.
This post is based on episode 1 of The Baggage Reclaim Sessions. [Listen to the full episode here].
The patterns that keep you stuck aren’t permanent; they’re just well-practiced. Break the Cycle helps you understand why you keep ending up in the same relationship with different people.
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