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Writer's pictureAshley Bugge

The Dating Conversation

The elephant in the room. The burning question. The time to start “moving forward.” The dating conversation. Whatever we want to refer to it as, it’s time for it and it’s here. There’s no comfortable way to go about this, to admit to all of you, that I’m ready to start moving forward and seeking happiness in this area of my life as well.


The honest truth is, I have been on dates. I’ve been dating. I’ve let my heart open to the idea of a relationship, to love, to a new vision of what happily-ever-after might look like for the kids and I, as a widow and as a mom to kids who miss their dad. And in the process, I’ve met some really incredible people, each on their own journey seeking their own version of happily-ever-after, but with their own set of complicated past relationships and baggage.


You all know my baggage, you’ve seen it played out through this blog and on social media over the past nearly two years. But you don’t see the guilt I feel inside, the fears I have when it comes to dating and love, or the awkward things that go through my head.


I’m used to being married, happily married at that. I’m used to a husband who runs to the store for a few things and brings home flowers because he knows they will make me smile, I’m used to inside jokes and taking turns watching each other’s TV shows, of knowing what to expect, of having a shared calendar and of being able to make plans for the future together. Because I’m used to this, and it’s what I’m comfortable in, I find myself expecting that of my date-ees. Instead of “tell me where you see yourself in ten years” I’m already planning out where our combined four-or-five-or-six-children will sleep, of if I would ever officially get married again, if they’d be a good step-dad to my children, if this is somebody I could see myself with long term. Before I’ve even met their family, I’m envisioning the combining of our own and deciding if it would work – or not. It’s an odd thing to admit, but it’s the truth.


It’s excruciating, but I feel this weight on my shoulders of needing to make sure I make the right decision, just as I’m sure a lot of you in the dating pool do as well. I don’t want to casually date, I want to find the person who will make me laugh, who has a kind heart and a great smile, who will love my children and hold my hand as I recount stories of their dad, who understands I will always love Brian, but that I’m capable of growing room in my heart for more love – just as I did when each of my babies were born. Who wants to love me, and let me love them in return.


In the vain of being completely transparent through all of this, I thought I had found that. I met a man from a former life of mine, who met all of those ‘checkmarks’ and wanted all of the same things as me. A very special human with a heart of gold, with his own baggage in tow, who, if the stars or timing or life circumstances had aligned, would probably be my post-Brian-happily-ever-after. However, due to circumstances outside of my control, we just couldn’t make it work, and I find myself back at my computer, a fresh set of tears on my worn keyboard, this time mourning the loss of something and someone else. Not just the loss of this recent relationship, though my heart does have a fresh wound in it, but the loss of the tight grip I had on my marriage with Brian. If I’m able to move forward with somebody, if my heart is able to feel this heavy towards the loss of a relationship with another man, I feel like my attachment to and with Brian is slipping, and that’s a loss in and of itself which is hard to explain to anybody who hasn’t lived this. That has very little to do with the reason this relationship didn’t work out, but now that it’s over and I’m having to go through my first break-up, post becoming a widow, it’s stirring up a lot of emotions and memories and questions and concerns. I’m a stubborn, independent and determined woman who has quite literally spent the last almost two years fighting for my life, and I’m used to doing this all on my own now, so I find myself at a disadvantage when it comes to figuring out how to “just date."


This post is all over the place, I just needed to say that today, I’m sad. I’m sad for what was, what could have been, what I had hoped for, and what I had envisioned. I know, without hesitation, that I will get through this, that I will learn from it, make a plan and come out better, stronger, more resistant than ever before, but today I am sad, and I wanted to share that with you.



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