How To Move On From The Past When It’s Right There In Front Of You

Q. Dear Jordan,

I have a question that I feel like you might be able to relate to.

I fell in love with [a famous musician]. Without going into telling details, I helped shape his now incredibly successful and lucrative career. 

We’ve lost touch and he’s only gotten more successful. He has children now, and I am a relatively new mother. Mutual friends keep me informed of the goings-on but it only takes the laziest of Google searches to see that he’s still traveling the world and making music.

I’m happily married and living in a quiet, midsized city now. Lately, simply thinking “what if” has now snowballed into thinking of him somehow every day – a lot of which is prompted by just turning on the tv or going on the Internet. I feel a great deal of guilt sometimes. Luckily I am with an incredibly confident and secure man, but I do feel like this burgeoning obsession could eventually be not great for us.

For what it’s worth, I would never be with this man again. I know we were not meant to be. But I feel like I need closure; some sort of real conversation to move on.

I feel like you could possibly relate – what with your relationship with Rob McElhenney and the fact that you are in a happy relationship now. We wouldn’t be where we are were it not for our past, right?


A. I think this is a really interesting question, and the reason that I wanted to address it here is that while it may seem like a very specific situation, having dated a person whose life events continue to be something that you’re aware of because they’re a public figure…it’s actually a problem that I think comes up for almost everyone at one time or another. Everyone has people from their past – exes or coworkers or friends – with whom they could have made different decisions, and it’s always possible that those decisions could have significantly impacted their life in one way or another. And everyone, from time to time, wonders “what if?”

Nowadays it’s not just the memories that leave you wondering: thanks to the Internet, these people from your past often end up right there in your line of vision, making it difficult not to dwell – especially if things don’t feel like they’re going perfectly for you at the moment. The problem, of course, is the one you pointed out: that it’s easy to construct a fantasy version of events, and easier still to get bogged down in bitterness, anger, or jealousy when you see these people rising to become stars in their fields, or going on glamorous vacations with their seemingly flawless families, or even just existing in a world that no longer includes you.

The question: how it possible to ever truly move on from your past when it feels like it’s always right there in front of you?

Facebook and Google have given us handy-dandy ways to check in on – and yeah, sometimes even obsess over – everyone from ex-boyfriends to frenemies to that girl who beat you out for that job you really wanted. But – and this is a big “but” – it’s important to remember that 99% of the time what you’re seeing is an extremely sanitized version of reality that has been presented for public consumption. And that’s not slighting anyone, not at all; it’s just the nature of social media: most people put up photos or status updates that speak to the things that they’re proud of or excited about. And so when you decide to check out what’s going on with someone who used to be in your life and isn’t anymore it’s very easy to slide into a pit of wondering what could have been…if only because man, what they’re up to looks so great.

Sure, your situation is arguably more extreme, and I get why it can feel overwhelming: you see your ex on a show, or accepting an award, or generally being fabulously wealthy and world traveler-y…and even though, as you say, you know you could never be with this man for your own reasons, it hurts. He has a lot of things that are very easy to romanticize, and very easy to want…and of course it’s difficult, feeling that you played a part in his success and aren’t reaping the rewards that are now coming his way.

I understand entirely where the negative feelings come from: in the months following my exit from Rob’s show, I was fired by my management team, downsized from my agency, and forced to completely reconsider what I was doing with my life while simultaneously watching my friends – friends whom I had worked with for years, whom I had loved and trusted – going on to do awesome things, career-wise.

Not fun.

But it would have been the same thing if, say, I had lost my job at a magazine and then watched a former coworker rise to become editor-in-chief. Forget the whole “money and fame” thing: when you want something that someone else gets, it can feel unfair. It can hurt. While of course we all want to be happy when others experience success, sometimes – like when the success involves something you feel that you want and need and deserve – that can feel almost impossible.


If there is one thing that my experience taught me, it is this: dwelling on the past and wondering how things could have turned out if only you had done something differently is a toxic way to live. Trust me, because I was there: I lived in bitterness for years, and it did nothing but make me sick in my body, in my mind, and in my soul. And what I learned at the end of it all was that living in the what-if does does nothing – nothing – positive for you, or for those around you. Hard as it may be to get past these feelings of jealousy and anger and sadness…it’s worth the work.

I spent a long time feeling angry that I had contributed to someone else’s success and hadn’t been “rewarded” for it…but I was not responsible for my friends’ successes; they were. They were not responsible for my happiness; I was. That was a difficult thing to come to terms with, but it was also one of the most valuable lessons I’ve ever learned.

I talk about this particular episode in my past on RG from time to time because the lessons that I learned during that period in my life were valuable ones, and because I know that things like career struggles and major breakups can be heartbreaking and make you feel completely at sea, and I want to offer advice and encouragement to whatever extent I can…but I can promise you that there is a time when you will feel that what’s done is done, and be glad for it. My own “what ifs” went away long ago, in large part because I made a conscious and active decision to learn from, accept, and then move on from what could have been, and that decision gave me the ability to focus on the present and reexamine what I truly wanted. And I mean it when I say that there is nowhere – nowhere – I would rather be than exactly where I am.

So let’s talk concrete advice, because it’s not always as easy as “focus on the present”. My honest opinion is that you should not be listening to your ex’s music, or seeking out his videos, or searching for him on Google. You should not be making him a part of your day-to-day life…because he no longer is, and that’s just the truth. As fun as it is to gossip about famous people – hey, I subscribe to US Weekly – in your life, he’s not a famous person: he’s your ex-boyfriend, and just because a photo is on the cover of a magazine doesn’t make it “funny” instead of “painful”. You need to ask your friends to please stop updating you about your ex’s activities, the same way that you wouldn’t announce to them that you saw their ex on Facebook and his new girlfriend is just gorgeous.

And while I completely understand the desire for a conversation that will give you “closure”…I have to tell you that I don’t believe that this is the solution. Think about what it is that you’re hoping to hear him say (that you contributed to his success? that you are the love of his life? that he’s miserable?), and then be honest with yourself about the chances that those words are what you’re going to hear.

This is not about him, and nothing that can come out of his mouth will be a magic pill that makes everything different: you are the one who needs to say whatever those words are that you need to hear to yourself. If what you need to hear is that you were important to him and that you contributed to what he has achieved, say that to yourself. Know that. And then move on.

I read a review in People the other day about some “how to be happy” book or another, and what stuck with me was a quote from the author when she was asked whether money made you happy. And her answer – in essence – was that you need a certain amount of money to not be unhappy (in other words, enough money to feed yourself and your family, put a roof over your head, etc), but that beyond that point human beings very quickly adjust to their circumstances, after which their happiness levels return to their original baseline level. All those things that you see your ex having and doing and experiencing are lovely, I’m sure, but they are in no way superior to what you have: a family who loves you, a home, and a life. I mean that.

Moving on from the past and focusing on your present and your future isn’t just a good thing…it’s a necessary thing. And I promise you that you can do it, but the answer doesn’t lie with a phone call or a conversation or one last Google search that turns up something that reveals that your ex’s life isn’t picture-perfect: the answer is with you, and your recognition that there’s no better place to spend your time than right here, right now.

*Question edited and reprinted with reader permission.

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