300 Writing Prompts #3: Dear Diary | Side B

Sometimes, a topic is so good that it makes you want to write more.

And to that, I ask… why not?

Write a diary entry dated 10 years in the future.

Friday, November 16, 2028

You know the good thing about Fridays? It is the benchmark of a job well done if you have the weekends off, which I am so fortunate to have. The last day of work before you can relax from the daily stress of your occupational job and move all that attention to your other job. In my case, I get to focus all of my attention of the lovely lady that awaits me when I get home. Hopefully, her bags are packed (and she didn’t pack too much) for our getaway to Maui.

It has taken me nearly a year to secretly save up the money, plan the trip, and arrange everything with her job without her knowing. She nearly caught me several times because of my careless joking but I managed to spring it on her only to be hit with the most brilliant smile I feel a person could make… following by several heavy hands blows out of disbelief… and finally a huge embrace that made all that time planing totally worth it.

Oddly enough, it wouldn’t have been hard to find this out. I kinda pushed us into watching Moana several times this year and has been playing the soundtrack to her annoyance. I mean, what I can I except…

giphy (2)

But I am really glad she is excited about going.

And I am equally terrified about the trip itself. See this lovely paradise we are traveling to is suppose to be the spot where I am going to ask for her hand in marriage and my head has been constantly tearing itself apart in anticipation. Anxiety has never really been a concern until now. Having been traveled all around the worth with this woman for nearly ten years, you would have thought I would have locked her down long ago but past relationships and issues has always made me hesitate.

Don’t get me wrong, I am not against change. I actually for it and I love pushing myself in uncharted territory. However, I can admit that I don’t like losing things. I don’t take it very well. So though I am perfectly willing to take that leap of faith and will probably do so without hesitation, at the same time, I fear the outcome and it weighs heavy on me.

But before I dwell on this any more than I should, I am going to stop here. I have written about these fears more than enough in other entries. Just know future me, when you go back to read this, regardless of the outcome, I supported your decision.

This time, you controlled the narrative and took charge and that in itself is an accomplishment considering our past. If you don’t remember, take a peek back.

Here is my message to you though. Whatever it is you are thinking about it, don’t wait like I did. Go for it. You have nothing to lose and you won’t be able to move on to that next great idea until you do it. I wish I could our younger counterpart that bit of wisdom but I will leave it to you just in case you forget.

Push forward and try all the things you want. At best, you fail and it was fun. At worst, you don’t and you regret not trying.

Winter at 37.

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