Starting Over


I was 11 weeks into seeing this guy who I really, really liked. I loved his kids. Our kids loved each other. My kids liked him. We had fun together. It was the first time I liked someone enough to start fading them into the melting pot of my domestic life, and while it was crazy having 5 kids at the dinner table and watching the frenzy of children on bikes riding around my cul-de-sac with the dorky “Kids at Play” sign at the end of the street, I thought it was something I could definitely get used to.

I realized you could really, really like someone and still notice the red flags. I lacked this ability in my 20s. Or if I saw them, I certainly ignored them. That led to a cascade of painful experiences I could have circumvented. Now a widow in my 30s (with more clarity and experience), I expect myself to freaking heed those red flags. If not for me, at least for my children’s sake.

That’s the thing. With children, everything weighs more. Concerns and fears and what-ifs sit like boulders in the pit of my stomach while I dither over decisions that will impact the household. I’m their only parent and they trust me unconditionally. I do not take that role lightly. I also know how limited and precious our time on this earth is, and I want to make sure I maximize my own experiences.

It just wasn’t going to work with this guy and his current circumstances. Those wonderful 11 weeks came to a screeching halt.

I am still bummed out about it. I loved his kids, truly, in a would-give-them-the-shirt-off-my-back kind of way. My son told me that the guy was “so nice to us, he was never fake nice.”  My little one told me tonight, “Can’t you just like him a little bit?” It sucks to let yourself get invested for what feels like nothing.

I am a ruminator. I go over details again and again and try to analyze whether it was the correct decision.

Should I have kept my mouth shut and just enjoyed the fun we were having? Should I have pretended those red flags did not exist? Should I have given it more time? Am I overreacting? Am I making up concern where there shouldn’t be?

Ultimately it ate away at me. I felt that I might be steering my ship (the one with me and three small children onboard) toward a situation in which I would continue to get invested and the circumstances would indefinitely be unresolved. I was scared there would be a lot of people with hurt feelings. I did not feel secure in the relationship, and I worried I was maybe wasting my time. Whether that was true or not is probably up for debate, but it’s how I felt, even when I was also feeling simultaneously very happy with him.

But that’s the thing.

How do we know if we are wasting our time? How do we know hurt feelings weren’t worth the risk? How do we set aside our concerns to allow ourselves to just be happy? Where is the line drawn?

It’s one of those things we can’t fully know ahead of time. It’s all a gamble.

And I am a terrible risk-taker.

So here I sit with my decision, not sure if it was a good one, mostly confident it was the practical one, but still feeling crappy about it. It doesn’t feel good to end things with a person you actually really liked.

But is “really like” enough?

I learned in my marriage to my late husband that no, it’s not. You need to really like a person AND feel secure in the relationship. That takes solid communication and the ability to follow through with action.

I keep telling myself that I can’t be afraid to start over. Start from scratch. Back to square one.

THIS is really what we fear the most.

Starting over.

Sure, we miss the individual. But it’s so much bigger than that. It’s having to confront the daunting task of letting everything go and doing it all over again from ground zero, even when it hurts. Even when it hurts so much you just want to go crawling back to the safety of what once was.

It also opens up other cans of worms. Like, maybe there is something defective about me? Or maybe I’m just not the type of person who deserves to find someone? Or…or…or??

I remember going through all of that when my husband unexpectedly died. I distinctly remember thinking: holy shit, I’m single. What do I do with that? You get in the habit of wearing yoga pants all of the time and not caring what you look like first thing in the morning next to him, and you just take it for granted that this kind of comfort will always exist.

Until it’s gone. The security evaporates, and out comes the mean voice inside your head that tries to convince you that everything is hopeless and dire and that you will never deserve to be happy again. Maybe you will never find someone else. Maybe that is the card you drew in life. Maybe you should resign yourself to unhappiness.

And you start to get scared. You begin to guard your heart more fiercely. It’s hard to know when to risk allowing yourself to let your guard down.

Kenneth’s death shoved me into the deep end of that kind of insecurity. I’m still learning how to swim. But I know that I can swim. I didn’t sink.

And I won’t sink this time either.

You can know something but still feel sad about it. I know I will most likely meet someone really cool who will effortlessly slide into a relationship with me and I will trust him. I know one day I will be so happy it will feel like I discovered a new kind of happiness that I had never tasted before.

I can start over.

I will start over.

In anything that I do: relationships, work, projects, ideas, adventures, learning. I can start over. I have that resilience. I can start over even when it is scary as hell, and not only will I start over but I will do it better than before.

We stupid humans get attached to possibility. We let our expectations run rampant. When life doesn’t go as planned, we don’t know what to do with that disappointment and we tend to wallow in our anxiety when we are forced into a place of pain. We want to cling to the version of what was supposed to happen in our heads because that was the safe version.

I am in the process of detaching.

I am telling myself the story of how much I deserve to be happy. I will tell myself this story until I fully believe it. It might always be a work-in-progress.

Those short 11 weeks that I spent with the guy were some of the happiest summer weeks I have had in a long time. It gives me hope that there are more happy days and weeks and years in my future.

But first, back to square one.

I’m ready for it.


  1. I’m five years into widowhood. Three kids too, 15, 12, and 9. I have gotten engaged only to break it off and now am dating guy #2, a year in. It sucks dating with kids. Way too much responsibility and people depending on one’s choices. And like you say, now I see all these red flags I never noticed before. I wonder if being married so long let’s one see the pitfalls we didn’t see before being married, or if being older and wiser makes it different, or if the kids in the line is what makes us more cautious. Or is it that over protection of our hearts that’s holding us back. Either way, I don’t feel secure in this relationship either. He’s a nice guy,but… you know how it is. But I haven’t broken it off yet. I just know I need to, and like you say, it a hard to let go of decent, to hopefully find great. Good luck. Thank you for always sharing your experiences. Nice to know I’m not alone out there!

    Liked by 1 person

  2. Sorry to hear about your loss. I’m new to your blog and you seem to be not only gifted with an awesome view of life but that you can express it quite well. Looking forward to seeing more of your posts.


  3. You write SO VERY WELL, I enjoy each and every post. And I am a 64 year old woman in a forty year marriage. Different life than yours for sure, but I can relate to you easily. Keep it up!😊

    Sent from my iPhone



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