Dating Advice when You’re Terrified to Love Again

Are you scared you’re going to get your heart broken again?!  Well then you are in the right spot!!  Check out this latest post for dating advice when you’re terrified to love again and how to bounce back from that painful breakup!!

Before, we dive deep into the dating advice when you’re terrified to love again, let me tell you a story.  

A story with a happy ending.  

If you’ve been around Pails of Love for longer than a hot minute, you will know that I went through a pretty bad breakup.

He was my first love and I thought that I would never be able to get over him.  

I spent a long time dabbling in dating apps and a lot of guys were interested.  

But, after a while I noticed that a pattern was developing.

I would be vulnerable with them until they started to like me back and then I would subconsciously or consciously, or maybe a bit of both, do something to jeopardize the relationship. 

And every time it worked.

At the beginning of this year, I met a guy who I connected with on a friend level.  

We tried dating for a short while but I felt like I was being pulled into a relationship before I was ready.

I didn’t feel comfortable and didn’t want the commitment even though I liked the attention (that makes me sound super shallow but……) but I didn’t trust my intuition and needless to say the relationship didn’t last long.  Maybe a week or two.

And then I just couldn’t do it anymore.  

You can read more about my dating adventures and lessons here:

My ex moved on too fast

How to tell a guy isn’t actually into you

How to tell if a guy’s the real deal.

But if I am being totally honest with you right now every relationship or conversation with these guys on all the various dating apps left me feeling unsettled.

I just had a feeling of being unsafe.  

Not unsafe in a physical manner but unsafe when I thought about an emotional and mental connection with them.

Really I just felt like no one measured up.  

And, I was starting to question if I would really ever find someone who I had the emotional, mental, and physical connection with that I was so desperately seeking and wanting.

It seems pretty bleak doesn’t it??

Well just wait because I promise the story gets better.

Randomly, a couple of weeks ago I signed up for a paid dating app.

And I felt like I was striking out again, and again and again.

Then I decided to respond to a message that had been sitting in my inbox.

It was Farmboy.  

Farmboy and I clicked right away.

The conversation was easy, he asked me on a date quickly, and he has consistently followed through with anything I have asked him to do.  

And just like that my patterns of sabotaging the relationship were gone.  

I was ready to commit.  I was ready to jump in with both feet and not look back.  

Just like that Farmboy stole my heart.  

So what made the difference??

Well to be totally honest, I’m not entirely sure.  

His standards match a lot to mine.  

He has constantly accepted me for where I’m at for who I am right now.

We just kind of clicked right away and I finally feel ready to enter a new stage of life to see where this new road is going to take me.  

And I am pretty sure it is going to be an amazing ride.

But please believe me when I say I was absolutely terrified to enter into a relationship again before I met Farmboy.  

So if you’re here for this dating advice when you’re terrified to love again don’t worry cause I won’t steer you wrong.  

This post is probably going to bring up a lot of emotions and periods where you will need to self-reflect so if you need to bookmark this post and come back to it I totally understand.

Sometimes, we just aren’t ready to move on or accept the truth.

But Girl I have faith in you that you’re brave and courageous and can bounce back from any relationship that broke your heart.

Because I’ve done it.

Others have done it!!

And you will too!!

Okay, ready??  Let’s get into it…  

The first question I need to ask that the great Matthew Hussey brings up when we get our heart broken is this:  

What is your go to pattern that keeps you from being hurt??

Hussey says that most people usually fall into two categories.




I fall on the second one.  Everything for me was a joke.  

I made jokes to keep everything from becoming too serious.  And when I viewed the relationship like a joke it kept me from getting too attached and hurt.    

So tell us in the comments below which pattern do you think you fall into??

This will be important to reflect on as we give the dating advice for when you’re terrified to love again.

Because we have to talk about honesty, vulnerability, and letting your guard down.

Which can be really hard to do.

The first thing to get over heartbreak is this:

GET BACK OUT THERE and GO ON DATES (even if it is just a FaceTime or Zoom Call)

When you take the opportunity to go on dates it allows you to feel reenergized and reminds you that you are an attractive person and that there are other men who are interested in dating you and getting to know you better.

But hey!!  

Don’t worry if you don’t feel like dating someone long term.  

It’s totally okay if you just  are dipping your toes in the water to get back into the dating game.

Because that date you go on…

All you need to focus on is finding immediate and spontaneous connection with someone. 

 It’s not to focus on a long term relationship but rather just strenghting your dating muscle again.  


A big part of being ready to get back into the dating game is being able to let your guard down.

TO let your guard down you need to be willing to truly be sincere in the conversations that you are having with others.   

A way to start being vulnerable again is to talk about something that you are passionate about without any sarcasm or jokes that offset an opportunity to be vulnerable.  

Another opportunity to be sincere and vulnerable is to compliment that person sitting in front of you.   Compliment in sincerity not with sarcasm.

And then talk about your weaknesses.  

Not those skeletons in the closet that you just share with anyone but things like…

Leaving your eyelash falsies around the house after wearing them and your family calling them caterpillars…

Those kind of weaknesses…

When you are ready to be vulnerable and sincere you show another person that you are still human.  

These human vulnerabilities can come even in the small things that happen on a date like telling the other person that you are nervous.  

I know that the first date that Farmboy and I went on he did this.  And it made me feel more comfortable.

Because I was liking him and feeling just as nervous as he was.  

And I am really really happy that I didn’t shut myself down to the new experiences that have come with meeting and getting to know Farmboy.


Remember when I told you that one of those guys I met on a dating app was really pressuring me to be in a relationship with him??

Well know that it is absolutely okay to just casually date!!

Other people might try to rush you into a relationship but it is absolutely fine to not want to jump into a relationship with anyone.  

It’s okay to trust, know and accept that a relationship will grow organically just like it did with me and Farmboy.  

Although things happened quickly it has felt very natural and everything is moving at a comfortable pace.  

He wasn’t begging me to be in a relationship with him.  

He has always been willing to give me space and time just to be me.

And I love that this is his attitude.  

He hasn’t been holding on too tight or moving things faster than I am ready.

And that’s what it means when you allow the relationship to happeN at a normal and comfortable pace that you and the other person feel comfortable moving at.   

You never should have to beg someone to be in a relationship with you and someone shouldn’t have to beg you to be in a relationship with them.  

The right person is out there.  Don’t rush it.  Take your time.  Your patience and perseverance to find the right one will pay off.  

So, it’s alright to accept that you no longer need to put your life on hold and now is the time to start creating new experiences.

One of the hardest things about a breakup is feeling like we need to place our lives on hold just in case…

Just in case… that person we loved and are mourning the loss of decides to come back.

But the greatest gifts that we can give ourselves is the gift of creating opportunities to be a part of something bigger.  

A part of bigger experiences and opportunities.  

To create new memories and experiences.

Because when we see others and are seen we can create beautiful meanings in our life from the interactions that we come to have.  

And we will also create meaningful experiences that we can learn from.  

These experiences can teach us not only more about others but a lot about ourselves and just who we are and who we can truly become.  

It’s a constant lesson for me that life is short and I can’t put it on hold waiting for the things of yesterday.  

Now, it’s time to reflect and learn from the past; What Lesson can you take from your breakup??

If asked at the beginning I would have said well he taught me about healthy relationships and about what true love looks like.  What healthy commitment and attachment looks like.  

And yah that is the logical answer to the question….

But is that really what I learned if we broke up?!

Well yup that is the logical lesson.

Along with this:

If someone is questioning the relationship let them go the first time. 

Don’t keep begging for them to stay.  Don’t keep trying to convince that person that you are right for them.

  It is super degrading to try to explain to a guy why you’re good enough to date him…

It’s a super disempowering place to be in and it leaves you feeling pretty yucky…

And you never fully bounce back from that conversation.  

I also learned that I needed to voice my concerns about those yellow flags that I saw… or maybe lets be honest they were probably red… but I don’t want to talk about that right now…

Now, you are probably wondering what is the emotional lesson I learned…

My behaviour before starting a relationship with Farmboy would be that I was not going to invest because I’ll get hurt.  

Remember, that I would do anything to jeopardize the relationship.  

So my man Matthew Hussey taught a mindset shift that really helped me to empower my actions and reflect on what I needed to change. 

And this is what he said…

WE have the power to change how we view our past and the lessons we take away from it. 

WE can’t change our past and what happened yesterday but we definitely can go back reflect and take a new lesson away from a painful past experience.  

It is time to create a new meaning about that past experience that hurt us.   

It’s okay to accept and realize that it is sometimes important to take a risk when we don’t actually know what the result is going to be. (. Really this needs to be a post in itself)

And recognize that there will need to be times where you communicate more, and know that relationships on any level create some pain and pleasure. 

The only difference between dating someone and someone you are friends with is the level of investment that is given. 

I am sure you can think of times where your best friend has fallen short and you have forgiven her.  That friendship probably causes you pain and pleasure and that’s okay.  That’s how it is supposed to be.

It’s important to know that rather than trying to avoid the pain of a romantic relationship you can learn from you past relationship by looking at it with new meaning.

The lesson to take away from your last relationship is that is it possible to recover.  

And it is okay, absolutely okay, more than okay to trust your intuition know when something isn’t right for you and have the power to walk away from it and leave.  

What keeps you and me in the stage of I am scared to love again is being scared to invest because we feel like we aren’t strong enough to walk away.

But girl, you and I both are strong enough to walk away from a relationship that hurts because we have done it before.  

And if this is your first heart break… we’ll then welcome to the breakup club.  

Grab some ice-cream, put on your jimmies, watch a sad movie and cry.  Get those feels out and then pick yourself up and get ready to move on and meet new people.  

I know easier said than done…

Now I am not saying that we should just throw caution to the wind and jump into a new relationship any time a guy shows interest with us but we can match their level of investment.  

You can invest and you can get close.  

But always remember… you have the strength to walk away when a relationship is not right and doesn’t validate who you are right now, what you need, and who you are trying to become in the future… (again this would make an amazing blog post that I’ll have to come back to!!)

 This leads beautifully into our next topic.  When our heartbreak has stemmed from abuse and cheating it can make it even more harder to be vulnerable and let our guard down.

Been there done that… and it really hurts.

So this is the time to ask yourself who do I truly want to be in this life??  

And then think of who you love the most in your life, and then ask yourself:  Am I setting the best example that I can for this person or the people that I love the most in this life??

Become empowered and allow your example to teach others that you are bigger than any pain that you have been through.  

Let’s be honest actions speak louder than words.  

So if you want to get that degree go for it, you want to take that art or photography class go for it…

It’s okay to validate how you are feeling.  It’s okay to be better than you were yesterday.  And it is definitely okay to move on and not wait for your ex to come back if he was a good one or trust that a new man in your life will treat you better than your past ex did.  

Please remember that you are worth it and you have the power to change and make a better future for yourself with a new man because you are worth it.

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