Ask the Addict: How to Know When It’s Really, Really Over

Each week, I’ll be publishing a reader question about anything – love, dating, being a 20-something, New York – you name it! If you have a question you’d like to ask, please email me (you can read more about Ask the Addict here).

Y: How do you know you’ve really let someone you loved go and that you’re ready to move on? Is there a time frame, a sign or something?

My take:

When I received this question my initial reaction was: that’s a fantastic question, I’m still wondering the answer myself. But after mulling over it for a week or so, I realized that though I’ve had trouble letting go of exes (cue Mr. Possibility’s dramatic plotline), I have learned a lot in the past few years about the moving on process.

For me, I knew I had finally let go of Mr. Possibility when I no longer felt the need to contact him when I was in trouble. It sounds silly but I kept him tucked away on a comforting shelf where I could pick him up and hold him close if I was ever stressed out. And honestly, for more than a year after we officially called it quits, I would still text him when I was upset. Or sad. Or frustrated. Or needed advice. Or simply to be held or told that I was truly fantastic.

Then one day, when something terrible and scary was going on, I didn’t want to call him. I didn’t want to text him or unblock him on Gchat just to see if he was there. I didn’t feel the need to have him in my life to fix anything or to rescue me from something that felt bigger than I could handle.

Instead, I convinced myself (and actually believed) that it was within my control. And that I had an incredible support system of friends and family that would drop everything to be there for me, so why would I want to invite this toxic relationship back into my life? No matter how handsome Mr. Possibility is or how much I depended on him when I first moved to New York, I’m not that girl anymore and we don’t have that connection any longer.

And for once, that was okay. In fact, it felt really, really good to not long for him anymore.

There is no definite time frame or a period that’s long enough to get over someone – it is really up to you and determined not only by the length of the relationship, but the importance of it. I didn’t date Mr. Possibility even half as long as I dated Mr. Faithful – but Mr. P meant more to me than any other man I’ve met, apart from my father. Letting go of him wasn’t just about getting over the relationship and the love we had, but also releasing him from the best friend role and finding my way in the city, without his guidance and support (even if his advice was often manipulative). It wasn’t easy and it took probably a little longer than I (and everyone who knows me) would have liked, but I did it.


My best advice is not to rush it but to also to not drag your heels. As long as you’re still talking to an ex (and let’s be honest, sleeping with your ex), you’re never going to let go. Even if you think you can have no strings attached and one day be friends, until you cut the chord for a while, you never will.

Try not talking to him for six months and even harder, not talking about him. The more you invite the conversation of a past love into your life, the harder it is to find a new one. Don’t keep reminders of him around your apartment or home, and utilize the block feature on your iPhone that not only keeps you from knowing if he contacts you, but prevents you from reaching out, too. Ask your friends to keep you balanced and level-headed and put things in perspective when you get lost in the what-if thoughts that plague you. (Because I assure you, they will.)

If you can put him out of your present, he’ll stay the past – as long as you let him. And then you have a chance of really moving on and finding that future that you so dream of. Your sign might be different from my sign – but you’ll know when it comes. How? Because the freedom is so, so incredible.

It’s like riding in a car in the hot, but not-too-hot summer, your hair whipping behind you and nothing but an open road — and an open heart — before you.lips-no-background

How to Love

This is probably the last time I’ll wake up with him, I thought watching the sunrise over the brick buildings on Amsterdam. It was a slow, gradual morning for the sun, just as it was for him. He didn’t move in the past two hours I was awake, other than to squeeze my hand and sigh silently into my neck, grazing his lips so slightly I could barely feel the tenderness on my skin.

I couldn’t sleep; my mind wasn’t interested in being anywhere but in this moment. I’m not sure what I was thinking when I responded to his text message after ignoring them all for over a week. Maybe it was because it was March and still a little cold outside. Or maybe I felt the sting of being lonely a little too deeply, and the thought of a warm body – especially one I knew as well as my own – was comforting. Nevertheless, I found myself waiting in bed, smooth and fragrant in a skimpy I swore he’d never see.

I asked him to call me when he arrived on the Upper West Side instead of ringing my apartment – I didn’t want my roommates to wake. I didn’t really want them to know, just like I was ashamed to tell my friends. And my readers. How could I preach one thing, promise another and then invite the shadow that was haunting me back into my life? Even if it was just for a night, the aftertaste always lingers much longer. And once you try it once, it’s easier to go back for seconds.

When I opened the door, he smiled that same sad grin I’d known for so long and tried so desperately to forget. But there was no wine, no girl’s night out, no one night stand, no anything that could really make me move on. I knew that challenge was up to me, and that I had been delaying the process by believing many wonderful, lofty things that really, I knew would never be. Especially with his hand massaging my back on the 10-step walk to my bedroom. Maybe it’d be like those dreams you wake up thinking about, but then  disappear from memory ten hours later. If no one saw him here, then maybe I could pretend it never happened.

But it did. And I didn’t hate it, I sighed as I slowly turned over to face him, trying my best to keep him asleep. He never drifted away easily and I didn’t want him to leave before the alarm made him. I studied his face as I thought about all the space between us. No matter how far we got or how much time we spent together, there was always a gap I couldn’t bridge. Now, we’re lying as close as two can get, and yet, I know I’m still nowhere near his heart. He used to tell me that organ didn’t work for him, and then he said he’d try to make it alive again, and now we’ve just stopped talking about it. Have I settled to being his sex buddy? I wondered, terrified of the truth. I placed my hand on his chest and curled into the nook I used to sleep in nightly and reassured myself: No, you’re just now the backburner. Not the frontrunner. Without making a sound, I let a tear get away, and realized that honestly, being on hold was worse than being used for sex.

He felt my weight against him as I sank into his side and he murmured something inaudible as he kissed my forehead and pulled me closer. I heaved a sigh of total confusion – knowing he would always want to be beside me like this, but never beside me in the ways that mattered. The ones that counted in any book I’d ever read. You’re awake, Tigar? he asked, nibbling at my ear. I nodded to where he could feel it but didn’t slip a word, knowing if I did, I’d say things I’ve said a hundred times. Things that have lost their meaning because nothing has changed. Because nothing will.

We cuddled silently until it was time to start the getting-ready routine – something we mastered in small spaces months before. I snuck him into the bathroom, wishing I lived alone just this once so I wouldn’t have to worry about the shocked faces or the disapproving glances I knew I would get, I knew I’d deserve. As I rinsed his touch off of me, wondering if he’d ever stay with me again, he started rambling about work and the week ahead. He asked me questions so casual you’d think we talked all the time, that we had never broken up, that I hadn’t been attempting to get over him for six months. He asked me about my plans and upcoming events, and I gave him simple answers to match his simplistic attitude that I felt weren’t nothing compared to my conflicting thoughts.

And then I dared to go there: Mr. Possibility- what did I teach you? Did I teach you anything from dating me? I asked with the shower curtain spread open, the water falling across my back. I didn’t care that my face was bare, that my body was exposed and my heart was vulnerable, standing before this man I couldn’t understand.

He didn’t miss a beat and answered: How to love. You taught me how to love, Lindsay. And he left the steamy room just as it was getting hot.

Months after this incident, where I’m dating and rediscovering the city through my lens instead of his, I find myself coming back to that moment. Back to those three words: how to love. For a while, I was convinced if that was the case, I must be a horrible teacher if that was his idea of true love or loving someone. Then I cursed my heart (for the first time ever) for being so unconditional, so understanding, so patient and forgiving. I let myself feel so many extraordinary things that weren’t felt in return, and in the end, I never got the apology, the answers, the anything I really needed.

But I did get a lesson. One very important, overly-dramatic lesson.

I learned there’s no course to study or class to take. There are many tests but never any measure of success. There are many words to write, but no rubric to follow. There are no answers to any of the questions or a correct bubble to fill in. The choices are endless, but the options seem limited. No matter the experience you endure or the hours you put into studying — there will never be a tried-and-true way to know how to love.

Maybe someone can teach you – the best anyone can teach something they’ll never fully comprehend or have the ability to describe. Maybe there are people who are shining examples of how to care for another person, and others who are quite the drastic opposite. Maybe the love is different depending on who wears it and who wears on you – but the thing about love is that it’s just a word until it’s put into action.

I may have taught him how to love but he never could translate it into something that meant something more. Into something that mattered in the ways that are significant. Those three words, where they be I love you or how to love – are meaningless until there are gestures and evidence there to support them.

So if every relationship teaches us something – as I have always believed they do – then that’s Mr.  P’s contribution. He’s made me see that love is so much more than words, no matter how often they’re spoken or sincere they can seem. And if he could never show me what they really mean, I know there must be someone out there who can.