Are You Ready? (The Unsexy Truth About Dating Again)

December 8, 2025

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lemon.capybara

Why “Getting getting back out there” might be the worst advice you’ve ever received.

I want you to ask yourself this one question.  

Are you Ready, Willing and Able?

If you’re here, you’re in the process of leading up to the “Ready” part, thinking you are “Ready” for what you need to do to find the partner you want to spend time with, get to know, and build a future with.

The “Willing” is on the horizon but you’re not quite there, and let’s not even get into the “Able” part yet.  It’s a process and you have to hit each one, consciously and fully.  Not trying to get woo-woo here, but this process is going to be a small part woo-woo, a dash of the technical  with a huge heaping helping of self love, acceptance and vulnerability.

What does “Ready” mean and how do you know if you are?

I used to be a jumper, someone who would hop from one relationship to the next.  No matter how long or short the “relationship”, I always had my back up ready and set up.  I had my safety net.  I had my next boost, my next potential “love” set up.  I never jumped without my parachute of “the new, the next” because being alone equated to failure and was scary as fuck.

It wasn’t until I was forced into a dating hiatus by my then guy best friend, that I learned about understanding myself and giving myself time to be “Ready”.  

I had layers of defense mechanisms in place, both to protect myself from the external and, more importantly, the internal.  After every end of a relationship, I shored up my walls a bit more, brought out the new sparkly version of me that attracted my next potential and kept up that facade until, well, until I couldn’t anymore.  

Insanity, am I right??

So for six months I didn’t date past the third date, and didn’t give myself any time to get attached to anyone.  Which left heaps of time (and space) for me to look at….well, me.  To sit in the very convoluted internal roiling hot mess of internal monologue, self worth, identity and general feelings of peace or lack thereof.  UGH.

My inner demon, the one that I had continually suppressed, silenced and ignored, this little being had been damaged with every end of a relationship, with every rejection, with every heartbreak and with every moment of “settling” I did to just be with someone.   Instead of healing each of these wounds, I slapped on some sort of cover, usually through another guy that gave me a sense of purpose, of interest and kept going, eventually only to be at the same ending.  Each. And. Every. Time.

But during those six months?  Oh my god, talk about a balm to my soul.  It started rough, painful and incredibly uncomfortable.  I had to sit in that funk, that disgusting sludge of my inferiority complex, fear of abandonment and self hatred.  

And sit I did.  Because to be Ready, I had to do something different.  I had to sit and take accountability. 

I wallowed.  I ranted to my close friends. I soaked myself in the toxicity of my inferiority complex, my fear of abandonment.  I blamed everyone, everyone but myself.  I was the victim.  I was the child given up for adoption.  I was the child who looked different and felt different.  I was the young girl with her first love, who had her heartbroken when he broke up with her to be with someone with more social cache.  I was the young woman who did the leaving, always, to try and lessen the pain of rejection and abandonment, who never let someone leave her again, all because of him, her first love.  I was the one that got rejected by some guys I liked, and pursued by those I had no interest in.  But still dated because they paid attention to me and gave me their time.  

It was so unfair and I sat in the unfairness of it all. 

Now I’m not stupid, and I’m also self aware.  Even then I had a grasp of myself, of accountability.  (You don’t grow up in my family and not know how to take accountability.)  I was self aware enough to not say “incredibly” but I was self aware enough, both internally and externally, that I started to see the common denominator of the sludge.  

“Hi, it’s me!  I’m the problem, it’s me!”  In the concise, brilliant words of Taylor Swift, they perfectly summed up the realization I came to within a month of my “alone” time, my self-inflicted, self-imposed (necessary) journey of discovery of myself.  With minimal distractions and band-aids in the form of some guy and the attention from said guy, to lessen the pain.  For the first time in my life, I gave myself the grace, the space and the time to reflect on myself, to learn about myself and to accept and start to love myself.  Well ok, let’s be honest here.  I was more shooting for liking myself.  Small baby steps people!

Until that point, I never really let myself heal from the rejections or the break-ups.  Instead I moved straight into the next guy and kept myself numb and convinced myself that I was happy.  I didn’t realize how hard I was running from my own feelings, my own thoughts, the fears those feelings and thoughts brought forth.  I saw and felt for the first time how scared I was, how damaged I was, how I tried to fix whatever was wrong in my relationships by finding a new person.  Forgetting that they might be new, but I was still there, the other part of the duo who was making the same mistakes, running the same scripts. 

I sat in the horrific funk, feeling like I was drowning, overwhelmed by everything I was saying to myself and minimized the noise, the distractions.  I stopped running and I started to see something.  

I was not “Ready”.  I was not emotionally or mentally “Ready” for anyone, for anything.  I was exhausted from all the running I was doing, and if you’re here, you know what I’m talking about.  Running from yourself is a constant never ending marathon, and you cannot keep up that pace long term.  Trust me.  

So, how do you get “Ready”?

You sit and reflect and you feel.  All of it.  There are no shortcuts here, only raw, visceral honesty that will rip into your heart and soul.  Things you thought you knew about yourself, you will peel that away.  Ideas you had about relationships, friendships, family bonds, all of it.  Because it all connects.  How you view yourself, how you view relationships, it all comes from the roots of you.  From how your family interactions were, how you felt in your family dynamic, in your friendships, in your first loves, in your broken hearts.  It sounds daunting and scary and who the fuck is going to want to do that?!

You.

Because you’re here.  Because what you’ve been doing hasn’t been working.  Because you are in pain, you are lonely, you are filled with questions like “what is wrong with me, why can’t I keep a relationship, why am I picking the wrong person, why does it always fall apart, and WHAT THE FUCK WAS I THINKING?!”  When you start asking those questions and SITTING with the feelings and honest thoughts and unfiltered responses those questions bring up, not running from them, not glossing over them, then, that is when you know you are Ready.  

Not to date!  Oh no my lovely, you have work to do.  The Ready?  It’s being Ready to do the work.

Ready to tackle the hard shit, the deep shit, the messed up shit that’s been nothing but hindrances to your life.  When you are here in this space, asking the hard questions, that is when you know you’re in the first critical part of Ready.  Some people go into therapy for this, some people have journals, and other people have inanimate objects they can talk to, scream at, cry to, and rage to, and they start to get it out.  All of it.  The heartbreaks, the lies, the letdowns, the could have beens, the trauma. 

For some, it’s easier to start maybe at your last relationship or the last break up.  You start to consider all sorts of things like why did you settle?  Was that really what you wanted?  What did you give up to be in that relationship?

This is an excellent starting point, especially because it’s a gentler entry into the harder questions and realizations.  I found when I started at why my relationships were failing (because they were) and almost walked backwards from the ending to the beginning, and asked those questions, I started to get somewhere.  It was no longer a simple “it just didn’t work out” or “I fell out of love with them”.  It was more corrosive than that.  But it was a shimmering slippery stepping stone to the deeper parts of the work I needed to do.

So sit with this, with yourself, with your safe space where you say the things that you’ve always been afraid to say.  That you knew going into that last relationship was a mistake that you knew from the beginning but you ignored the parade of red flags because what they provided was more necessary.  It’s ok, we have all done this, I promise you.  

So sit, and be at peace.  And when you’ve done that, go deeper.

Start asking yourself “Who am I? What do I want?” 

That’s it.  Two questions, they seem simple, but boy are they tricky.  

I went through that.  I struggled initially and continually with those questions and avoided really trying to answer them honestly.  Expect this.  If you’re doing it right, you are not going to like the answers.  In fact you probably aren’t really going to give yourself the honest answers, not initially.  You are likely going to run from them, and maybe ignore them, and get into another relationship to prove to yourself that you don’t need to go through all that sludge.  Because why would you?  You’ve got someone who is interested in you!  Someone who likes you!  And you like them as well (enough) and find them interesting (sort of) and they could give you what you’re looking for (you think).

How do I know?  Because I did all of that.  

I started to sit in the funk, the grossness.  I felt it crawl all over me and I was drowning in it.  So I went and found someone else to date.  He was nice enough, albeit a bit on the boring side but I told myself he was “safe”.  I went on three dates with him, so I was within the “rules” that were in place to help me be single and to take time to discover myself.  Which I wasn’t doing and instead distracting myself (again).  He asked me for a fourth date and I just couldn’t say yes.  Because it was breaking the rules.  Three dates only, focus instead on being alone and what I was feeling.  

What I was feeling was while he was nice, I didn’t really like him.  I liked that he liked me, wanted to be around me, but I looked forward to going home and sitting by myself more so than having him around.

Hallelujah!  The penny dropped.  At that moment, I knew I was Ready.  The normal adrenaline rush I would get from dating wasn’t there and I was honest enough to admit that.  Holy shit, was that a breakthrough?!  Ahhhh yes, yes it was.  And man talk about a rush!  I still remember it, the heart thumping, happy dance having, smacking myself on the forehead kind of rush that I felt saying no to the fourth date because I didn’t want to, because he wasn’t someone that I wanted to date, that spending more time would be taking time and focus away from me.  And I didn’t want the rest of my life to be continually filled with guys who liked me, but I wasn’t really into them, but stayed with them because it was better than being alone.  That wasn’t fair on them and it sure as well wasn’t fair on me.

When I wanted to sit in the near venomous tacky substance of my feelings instead of chasing the easy sugar hit of distractions, it was time.  For me.  

The first part took a while, about two to three months.  It was hard to not be jaded, to not be cynical, to not be judgemental, not to be self-loathing.  I wandered around in my head a ton, then in my heart, then into my relationships.  Broke them all down, broke them all apart.  I mourned the young girl who convinced herself to settle, I raged at the people who convinced her that she wasn’t going to do any better, and plotted some not so pleasant things at those who had hurt me.  

I healed.  Or started to heal.

I stopped dating.  I started to ask the sucky questions.  If I tried to ignore the question or tried to avoid the question was how I knew those were the right questions to ask.  I didn’t journal because I’m not really someone who journaled (or at least I wasn’t then).  I didn’t talk to any of my friends because I didn’t want to take up too much space and I didn’t want to feel that vulnerable with anyone.  And none of my friends were really in that space of self discovery or self betterment.  I didn’t get a therapist until years later.  I did this alone. 

I’m not necessarily recommending that you do it alone.  I encourage all kinds of supportive tools that you may need to help, but I am going to say that you need to do most of this alone.  What is important, what needs to be prioritized and focused on is that this is your journey.  This will be you going into yourself, finding all the hurts, the path of how you make decisions, the little treasure troves of what you want.  These are your hopes and dreams and what makes you wonderfully uniquely you.  This is when your voice needs to be heard, your heart has to be listened to, and when what you want cannot be influenced by anyone else.  

When I answered my hard questions, and let myself say the truths out loud, to accept that there was nothing wrong or ugly with my answers, that was when I knew I was Ready for the next part.  (Oh yeah, annoyingly there are multiple parts of Ready, Willing and Able.). 

Mentally, I was no longer basing how I thought or felt about myself and my worth based on someone liking me or validating me.  I knew that dating was getting to know someone, and them getting to know me.  Not the “me” that I thought they wanted but the “me” that I had spent time figuring out, the me I was still figuring out and learning to like.  I knew that I wanted something longer term, that I wanted marriage, maybe children.  I knew that I wasn’t looking for casual hook-ups, booty calls or someone who made me their second choice.  I was open to the idea that everyone was a potential, but I didn’t have to force someone into what I wanted or sacrifice what I wanted to fit someone else (well now I say this but I ended up in my first marriage in this exact situation, so I wasn’t perfect at this but I fucking LEARNED).

Most importantly, as part of my healing I started understanding myself.  I started to be kinder to myself.  I forgave myself, or at least started to, for the questionable relationships.  I decided that I wasn’t going to beat myself up for those relationships, that I was not going to spend any more time or energy on regretting the guys that didn’t get me, that took advantage of me, that hurt me and instead I was going to look at what I learned from them.  Then I took those lessons and I learned how to not make those mistakes again.  Or tried to not make them again, I mean I’m human so I gave myself room for mistakes and grace for when I made those mistakes.  

After those two to three months of being alone (the longest I had ever been single up to that point) I was Ready to put myself out there.  Oh sweet child of summer, I was so young and so naive.  I had done the work (or so I thought).  I had done my Sludgefest, and I was going to put myself out there for everyone to see how healed and self-aware I was with my new levels of self-respect!  

Then a funny thing happened.  I might have been Ready…but I wasn’t Willing.  For Fuck’s Sake (FFS) I had some more work to do.  And so will you.  

I’m Ready (or as Ready as I can be right now) so now what??

Next, you have to be Willing.

Don’t rush the Festival of Sludge. It’s where you become the person who is finally, truly, Ready.

See you in the next one,

Lemon Capy 🍋