How Many Times Can You Break A Heart?

It is the question you knew or know is/was coming from your kid or your nieces/nephews but knowing is far different from answering.

That is because the experience is different for different people and the depth is rarely if ever the same. People like to say that your first heartbreak is the hardest but it is not always true because the way you love and are loved by that other person isn’t always the same.

People like to say that your first heartbreak is the hardest but it is not always true because the way you love and are loved by that other person isn’t always the same.



Sometimes you get lucky and find someone who truly completes you and sometimes it is qualified by words like mostly or almost.

The mostly and almost loves are just as real as the truly but the parts and pieces that prevent them from being the same also tend to keep the heartbreak from hitting that same depth of ache and loneliness.

How Many Times Can You Break A Heart?

The question caught me off guard because I didn’t expect it to come from the girl who used to sit on my lap and ask me to read her stories, at least not yet.

I didn’t expect her to ask because she had asked how many girlfriends I had besides mom and I said 10,000. She had rolled her eyes and told me to give her a serious answer and I said maybe six or seven.

She had a couple of follow-up questions but none were particularly detailed and most were in regard to how old I was when I started dating or first kissed a girl.

The big follow-up came days later and since I was lost in thought about other things it took a moment to register.

I said I thought it was maybe five times and she asked if that meant it was five different girls and I told her it didn’t.

“Dad, did someone break your heart more than once?”

I just smiled and shook my head yes.

“Why did they do that?”

“I don’t think they meant to, it just sort of happened that way. Sometimes good intentions go bad.”

She scrunched up her face and I could tell she was thinking about it.

“Someday I might have to punch a few boys in the nose.”

She shook her head and said no.

“I might be the one who breaks their heart and even if I am not. I’ll be able to take care of it on my own.”

I might be the one who breaks their heart and even if I am not. I'll be able to take care of it on my own.Click To Tweet

I smiled and told her I was certain she would be able to take care of whatever she encountered and reminded her that sometimes it is not just ok, but important to ask for help.

“You don’t always have to carry the load on your own.”

“Dad, you never ask for help, why should I?”

I smiled again and told her that just because she had never heard me ask for help didn’t mean that there weren’t times I had.

Maybe I ought to blame middle school or Disney TV for this line or maybe I ought to just accept that some questions come no matter what we do.

The part that bothers me more than anything else is the question is proof that time is moving faster than I want it to, the kids are getting bigger at breakneck speed.

What Advice Should I Give?

The interpersonal issues that are cropping up now are far more challenging than the ones they used to lob at me. There is less talk about how to share and more about what not to share and with whom it is ok.

That is the influence of social media and the conversation that has to take place because kids don’t always recognize what could happen if they post certain things online.

But it is also trying to deal with and explain who is being friendly and genuine and who is a snake. Some kids at school smile while they stab you in the back, same as adults can and do.

People can be great and they can be awful.

It is hard sometimes helping the kids navigate these things because you have to let them figure it out on their own. You have to give them the chance to learn so they can do it without you and you do so knowing that means that some people are going to be awful to them.

It is not easy and it sucks, but it is necessary.

The heart wants what it wants and I know one day the kids will learn firsthand what it means from this angle too, but you’ll forgive me if I say I hope it takes a while for them to learn that particular lesson.

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  1. Daniel September 3, 2015 at 8:22 am

    Love this post! My oldest is 14 and she’s navigating the treacherous waters of relationships and recently dealt with the heartbreak of telling someone she was big time crushing on, that she was tired of him toying with her emotions and jerking her around. It’s a sucky thing to have to sit back and watch, as a parent, but it’s good that your kid is comfortable enough to ask you these things.

    • Jack Steiner September 4, 2015 at 9:52 am

      It is hard, so damn hard watching the kids go through this. But it is important for them to learn so that they know how to deal with it all when things get nutty and or go to hell because they will.

      The thing is once they figure it out they learn they can stand on their own or so we hope. 🙂

  2. Janine Huldie September 2, 2015 at 7:32 am

    I am truly hopeful that I have more time still for this with both my girls, but still I am with you on having had my own heart broken in the past and also like you one person in particular was guilty of breaking it more than once (actually a few times to be honest).

  3. Larry August 31, 2015 at 6:38 pm

    My older son is the same age as your daughter. I can’t imagine him asking me that. He has no interest in such things, and his focus is elsewhere . So, I don’t think you or your daughter will have to break his nose – well, at least not for a while.

  4. Chloe Jeffreys August 31, 2015 at 12:08 pm

    Sadly, lovers are not the only people who can break your heart. The worst heart break I’ve ever experienced came from a snake masquerading as a friend. I didn’t recognize until the knife was deeply lodged in my back.

    I wish heart break wasn’t such an essential part of maturity, but they are. And one day your daughter might find gratitude for the snakes that come into her garden. I think those snakes have more to teach us about ourselves than our friends and lovers ever do.

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