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

If I Only Knew

Looking back over my weekend I realize that the same theme kept popping up in conversation. First on Friday night with Lostplum and our friend from Thrillist and then today at with KB_in_NYC.

The topic was, if only I knew then what I know now (suprisingly, I wasn’t the one who brought it up either time).

The truth is, I can’t imagine what my life might be like now if I knew at 21 what I know now.  I was so utterly clueless then.  Clueless.  And of course I thought I knew everything. I am not in any way suggesting that all 21 year olds are clueless.  Just saying that I was.

I’ve been thinking about this for the past hour or so, and here are a few concrete things I’ve come up with:

  • I’m pretty sure I wouldn’t have married any of the men I’ve ever dated.  None of the knowledge I’ve gained about dating, men or relationships would make that play out any differently.
  • Back when I was 21 and the hot pilot I’d met in Paris told me to stay with him for a while/indefinitely (blowing off my final semester of college), I would have said yes.  A girl only gets one chance to be 21 in Paris.  I could’ve finished college a semester or two late.
  • I would’ve ended a couple troublesome relationships earlier.  Especially the one that seemed to eat my twenties.
  • I would’ve been a better breaker upper.  I used to be really back at it.  Nasty calls and emails and all kinds of ugly.  I’m much better at it now.
  • I would have travelled more, taken more chances, given my heart more readily.

I’m sure there’s more, but this is what comes to mind.  What about you?  What would you do differently, if only you knew then what you know now?


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9 to “If I Only Knew”


  1. OpinionatedGift says:

    For the record, all 21 year olds ARE clueless. I think we remain clueless until we are around 30, when we admit to ourselves we are clueless. I don’t think the clues start coming til close to 40…and at 47, I’m not too sure that’s true.

  2. Singlegal says:

    I would have still gotten married, but ended it much sooner. I probably wouldn’t have moved across the country to a place I never should have been in. I would have learned to control my diet MUCH earlier on. And I would have stuck with the Spanish lessons so I could be fluent now. Goddamit – I was good at it (still am, in some respects)!

  3. drumdance says:

    I believe that most of life is realizing that what you know now would’ve been really useful five years ago. Starts in high school and continues through, oh, maybe your seventies?

    In five years I’ll probably realize this was a stupid comment. :)

  4. Dont Be a Slut says:

    I would have said no to sexual overtures much more often than I said yes, and I would have valued myself a lot more.

  5. Jennifer-from-NY says:

    Hi, thanks Simone for the italicized bit. And thanks OpinionatedGift. I’ll write back here in 20 years and we’ll see (I’m 20). Life is about experience and learning so of course we all have to take chances to do anything at all and it seems most people regret not taking them. I’m a cautious person in general but I try to weigh possibilities while still taking chances. My parents say I have an overactive superego but I’m trying to bring out the id occasionally :)
    I loved seeing “given my heart more readily” as one of your things Simone. I’m still a little burned by the end of my first relationship so I’m trying to both accept it and be able to let someone else in at some point.

  6. starangel82 says:

    What a loaded questions. Twenty-one year olds are clueless. It’s just a fact of life. I really don’t think we’ll know everything until we’re in our 80s or 90s… then no one will listen to us because they think we’re crazy old ladies. Such is life.

    I have very few relationship regrets, but there is one. I wish I had told a certain someone how I felt many moons ago. I might be happily married now. Then again I could be miserable and broken hearted. I’ll never know and that’s what kills me.

  7. Simone Grant says:

    -OpinionatedGift
    A dear friend of mine (who is 51) keeps telling me not to trust any man younger than 40. He says that’s when you guys start to mature. :-)
    -Singlegal
    Oh god yes, the Spanish. I’ve spent so much money over the years working on that (including spending time outside of the country). And yet I never practice. Can we get a rewind on that?
    -drumdance
    And so, anything specific you’d like to change?
    -Dont Be a Slut
    Interesting that you equate valuing yourself more with rejecting sexual overtones? Last night a friend on Twitter responded to this question by saying she’d remain a virgin. Whereas I don’t have big regrets in terms of my sexual experiences. There were a few guys that were mistake, but I figure – you live/you learn.
    -Jennifer-from-NY
    Like I said in my post, I can imagine what the 21 year old me would do with the knowledge I have now. But I do know that I would have gotten out of bad relationships quicker, and moved on quicker and loved more. I spent a lot of time nursing my hurt and anger and disappointment. A lot of wasted time.
    -starangel82
    Yeah, those never knows do kill us. But I would like to think that things work out the way they’re supposed to. In the long run.

  8. BetterNow says:

    I am 24 and from Monday-Friday 9-5:30 I keep myself very professional for work because it is very hard to gain respect being so young…however after 5:30 and the entire weekend I enjoy making all the choices my parents warned me not to….I know the difference of right and wrong but at 24 I much rather make all the wrong choices (they are way more fun). I just dumped a guy that was “too nice”, I should feel bad but I dont because I dont want nice right now, I want fun and exciting. He deserves a girl that can give back what he can give to her and right now, that is not me . I am in no rush to be in a serious relationship and get married. I want to make and spend my own money, laugh, cry and travel with friends and network all over the place. I want to look back in years to come and say I did everything I wanted to and have no regrets. So many people I look at regret so much, I dont want to be those people.

  9. Simone Grant says:

    -BetterNow
    I love your attitude. Regrets suck.