Real stories about dating and relationships in New York City. Truth is more interesting than fiction.


Main Entry: mile·stone
Pronunciation: \ˈmī(-ə)l-ˌstōn\
Function: noun
Date: 1662
1 : a stone serving as a milepost
2 : a significant point in development

I’ve been thinking about (and writing about, but that’s for another time) milestones and the passage of time.  I’ve always tried hard not to get bogged down by the shoulds of life – I should be married, I should make more money, I should own my own home. But, and it’s a big BUT,  it’s hard for me to move through life without marking time and acknowledging the milestones.  Which I try to do non-judgmentally. Not being hard on myself. But we all know how that goes.

Anyway, I guess, since I don’t have the traditional ones (marriage, kids, house) I look to other things. For other things. Signs that I’m moving forward.  Moving somewhere. Somehow. Not standing still or going in circles.

And yeah, a lot of this has to do with the fact that my 40th birthday was just a few weeks ago.  And that I’m a hell of a lot less “settled” at 40 than I was at 30. Which is really pretty freaky when I think about it.

I probably should’ve warned you up front, this is one of those lame-ass posts that’s barely a post.  Just a bunch of thoughts, cobbled together.

I’d love to know what you think about the whole milestones thing.  Do you think about it?  What you’re accomplishing, what you’ve accomplished and where you are in your life?

Random sidenote – I’ll be dating again soon.  Just as soon as I’m back and able…

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9 to “Milestones”

  1. E, Seantrice says:

    I’m thirty-one and I’m in the middle of breaking off a two year relationship. I would’ve loved to be married at thirty and have kids by thirty-three. My plans didn’t work out but I’m going to make new plans that involve making me happy. My accomplishments won’t have anything to do with marriage and kids it’s all about happiness. We all know people who have the marriage and kids and are miserable. Apparently it’s not my time and I’m not going to rush it or make myself feel bad because I’m alone yet again. I started my own blog this year and that’s huge accomplishment for me, I put it off for years. It’s off to a slow start and it’s an internal struggle to continue. Your blog helps keep me motivated. Keep up the good work and don’t worry yourself about time just use it wisely.

  2. Terry says:

    I am 53 – my wife is having my first kid. Is that a milepost or a milestone? Probably. But not something I think about – .

    I guess I didn’t think I would be alive this long- so maybe that is one in itself. But just that I was luckier than some of my friends – that doesn’t seem like a real reason to celebrate. I’ve also been lucky that I’ve accomplished just about everything I’ve wanted to accomplish – but still, that’s more akin to checking off a list at the grocery store.

    I wish I had one of those great inspirational quotes that the late John Wooden had – but I don’t.

    Its not a “is that all there is?” sort of thing– but I’m finding milestones to be more of a great cup of coffee, a good conversation, and sitting in my backyard with a fine cigar and a cup of something. They are moments, not milestones – that I enjoy.

    • Simone Grant says:

      Your thoughtful post reminds me of a conversation I had recently. Someone asked me if I was striving to be happy (an odd question, I know). My reply was that I tried to appreciate the joy in my life. As much joy as I could find.


      So simple. And hard to measure. I guess I should try harder to live in the moment, eh?

  3. j@nycandlove says:

    I think concept of a milestone is something you can look back at as a life changing event, good or bad. They’re the times when you’ve risked it all and taken a chance on something or someone. When I look back at the things I’ve achieved they’re all defined by points when my life has changed in some drastic way, for example moving to new york, starting a new job etc…

    My biggest concern is that as I get older I’m becoming more risk adverse as I have more to lose.

    I definitely think about the milestones in my life, some of my friends would probably say I obsess about them far too much, but I think it’s important to keep your eye on your goals.

    • Simone Grant says:

      I can’t stand when anyone tells me I’m thinking too much – about anything. The truth is, some of us are very cerebral and stay hyper focused on goals and outcomes.

      Whether that’s ideal for our mental and emotional health? That’s another issue.

  4. Ian says:

    As John Lennon said, life is what happens while we’re making other plans.

  5. Jolene says:

    NOT a lame post, first of all. And I’m always thinking of milestones that are coming and milestones I want to create. I think it’s a great idea.

  6. Sandyvs says:

    I have trouble with time conception. Some good, happy events that occured many years ago seem like they happened yesterday, while some events (the bad memories)never seem to be far enough away from now. I have never been a goal oriented person, but every single thing that I have really wanted in life, I’ve gotten. What I have learned more and more as time passes is that it’s best for me to just kick back and let the universe make my life happen. I plan for the future, but I don’t worry about it. Because I’ve found that whatever I think will happen usually doesn’t, but the most surprising things do!

  7. Some say the purpose of life is to just be. We leave milestone markers for others to find after we are gone, not for ourselves while we’re alive. So think of every blog post as a marker which you are at once experiencing, building AND sharing with others around you. It is more sharing with the living than most people do their entire lives. And it builds more mile markers than most people will have after they are gone.

    My mile marker pondering, which I hope you enjoy as much as I have yours. :-)