So, Yeah, I Did Sleep With My Ex For Two Years…

Mr. Possibility and I broke up in one of those super-dramatic ways that you’d expect to see in cheesy romantic comedies that we all love to hate. Short summary: He couldn’t give me what I wanted emotionally, and even though I probably loved him more than any of my past boyfriends combined, I knew that settling for a half-hearted love would never be enough for me in the long run.

So after handing him his key back at a sushi restaurant while ‘If You Don’t Know Me By Now’ played in the background, I stepped out into the rain, hailed a cab uptown and cried my eyes out. I wish I was kidding.

A week later, he was whispering he loved me in my ear while going at it from behind so hard I orgasmed twice.

Continue reading

You Can Fall Apart

A few weeks ago an article went viral on how to cry in New York.

Like anything that makes fun or sheds light on the city, I opened it, knowing I’d relate to whatever it said. I laughed at the tips – wear sunglasses and have a good song to really get you in the sobbing mood – and I liked the link my friend shared on Facebook.

And then on Friday, after a particularly stressful day, I found myself overwhelmed with my ever growing to-do list and as I talked to my mom (our nightly ritual on the two block walk to the train at night) – and I felt them.

The tears start to well.

I pressed into the receiver, complaining about the stress of doing taxes and how freelancing makes everything complicated and expensive. I expressed my anxiousness over the half-marathon I was running on Sunday (that I ended up rocking!). I talked about how guilty I felt about being jealous of my friends and their sweet boyfriends that surprise them with dinner reservations and a night out dancing – just because. I basically screamed into my iPhone that it wasn’t fair that for the past two and a half (and counting) years, I haven’t felt a lick of any emotion toward any man. My list went on – far too melodramatic to continue here – and as I kept going, I couldn’t hold back the sadness anymore.

I stopped in front of a party supply store and turned away from the people passing me on the street to hide my embarrassing, splashing drops, and my mom tried her best to comfort me with euphemisms and words of encouragement.

I got off the phone, finding it too difficult to talk, and stood there, collecting myself in the cold weather, praying no one I knew walked past me. I had cried in New York – like I have many times before – but I didn’t have sunglasses this time. Or a song to listen to. Or even tissues.

I avoided eye contact and kept my head down on the train home, willing myself to just make it to the UWS before collapsing on my bed, Lucy greeting me with her worried face and diligently licking away the salty mess. And though the article was right about ways to go about crying in New York, I’ve always found it hard to fall apart.

Certainly in public and often times, not even alone.

Somehow, letting it all come pouring out feels like opening the flood gates to something I don’t want to reveal or even see for myself. Why open the doors when denial feels so warm and protective? If I let the stress build and then I admit that it’s heavy, I fear I won’t be able to pick it up again, paralyzed by the thoughts themselves.

Falling into negativity doesn’t wash away the despair, it just heightens it.

And so, I mostly keep it together. I sing little mantras in my head for when I’m nervous. I remind myself that most everything is temporary and the best thing about life is that it always changes. I hold my head high and I try to count the things I’m thankful for instead of rhyming the things that make me bitter. I believe in the great tapestry of the universe and that I will never be dealt a hand so bad that I can’t handle it. I try to place my faith in the goodness, the boldness, the kindness of the world – and of this city – and thus, by merely having hope, I have strength in my heart.

But sometimes, like on Friday, the best possible thing I could do for myself was to let it go. To allow the thoughts to race through my mind, dangerously close to the edge of reason. To watch myself spiral wickedly out of control, witnessing my emotions like an outsider, seeing the adult tantrum take form, and eventually, end.

Because the thing about falling apart is that once you do it, you feel lighter. Those damning feelings don’t read as threatening anymore. Anger, jealousy, fear – whatever was building within you – go from boiling to simmering to frozen. Sure, there may be messy tissues and mascara-stained pillow cases, but once you’re finished, once you really release it, you’re you again.

And the world can see it.

Everyone around sees the weight that lifted. Your eyes are clearer, your head is not as cloudy, you’re smile is more generous. And perhaps, you attract something – or someone – just by releasing the tension you were clinging to for far longer than you needed to.

So you can fall apart. You can let it all hang out. You can lose control and have a meltdown. You can curse the world and fear your future. You can watch everything crumble and break, and you can bend yourself to the negativity. You can cry your eyes out like you have so many times before.

But then, you have to get up.

And though you may fall apart again and again and again – what’s more important is how many times you pick up the pieces and put yourself back together. The mark of a person is not how many times they have suffered or failed or been disappointed, but how many times they have said, “Okay, I’m done. Now what?”

So go ahead. Cry. Let it out. Let it go. And then figure out what comes next. Because trust me, there will always be something more – something better – to come.

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.

The Way I Heal

Months after I officially ended everything with Mr. Possibility, I still found myself responding to emails and text messages, analyzing the intention between the lines, and keeping myself awake long enough to wait for him to arrive at my door. Allowing him to stay in my life – and yes, in my bed – felt easier than ceasing contact.

But even as I held him at an arm’s distance, my heart was already much closer, so letting him hang around and inviting him into my life wasn’t a healthy tactic. Procrastination though, tasted better than swallowing the bittersweet prescription I knew was coming. After many failed attempts to make him want me how I wanted him to desire me, after biting my pillow so he wouldn’t hear me cry at night, after convincing myself that being around him would awaken something that never lived inside of him to begin with, after lying to my friends about where I was and avoiding my mother’s phone calls – I finally got the message loud and clear.

From him, on Gchat.

It was straightforward and blunt, without a hint of consideration or kindness, and worse, void of love. Or at least the kind of love I want and deserve. When I couldn’t make meaning out of emptiness, I signed off and deleted the evidence of the relationship. I finally totally severed communication and packed away anything that took me back to better days so I could finally face the day I was living. And though the art of getting over someone is something I’ve yet to master or totally understand, I set my mind to letting go and moving on, no matter how badly I wanted to reach for the phone, type an email or share a bed with a man I once was in love with.

While I can talk about most anything on this blog, sometimes revealing a bit too much — forgetting that the Internet is truly an irreversible medium — writing about Mr. Possibility and what really followed our dramatic demise has been incredibly difficult for me. The final post of a year of writing – where I valiantly headed out on my own, telling him to go where the sun didn’t shine and standing up for myself, was a true story. I felt empowered in that moment: ready to conquer heartache and eager to be alone.

But if I’m honest, as I always have been in this space – I wanted the chase.

I watched and helped him attempt to win back his previous ex (who is now one of my closest friends and the best dose of reality on the topic of Mr. P), and I listened to him mull over the past he regretted. I heard all of his past love stories and I wrote the one I thought we had, post after post, day after day, praying that I would be the girl who changed the unavailable man. And even in my grand departure, even in that yellow chariot that sounds entirely more fabulous than it really is, a part of my heart was still holding onto the hope that he’d come running. That in my silence, he would find that same ache I’ve had since practically the day I met him — that lingering longing to capture the attention of something that’s unattainable.

But he didn’t come to my rescue.

He didn’t shower me with hand-written letters to why I should give him another chance. There was no romantic gesture, no fight for my love. There wasn’t even much of an apology for the ways he had been cruel when we were together. He happily accepted my offers for companionship and was careful to remind me how amazing I am – but that he still wasn’t in the market for a relationship. A year-and-a-half later I’m in a totally new part of my life, and he’s still almost exactly where he was when I met him: uncertain for the future and unwilling to compromise for anyone else, but sexually inclined to see what this city has to offer.

I didn’t want to admit that I went back to him, thus causing myself more  disappointment than if I had ceased contact in September. I had been down this road before and I knew where it led, but I ventured on the path anyway, fooling myself into thinking the destination would be different.

And when it wasn’t – I was ashamed to confess that still, even after all this time, my heart still hurt. It felt weak and silly to be someone who writes about such topics for a living and can’t take her own advice. To be someone who is mainly open and candid about everything, but unable to reveal that underneath the clever themes and rhythmic sentences, there’s a woman who sings along to Adele and runs to Kelly Clarkson, who wears big sunglasses to cover the tears, concealer to hide the dark circles, and still has to block Mr. Possibility on every social media channel so I don’t draw conclusions from things I can’t confirm. Behind the blogger who dishes on everything, is a woman who had a hard time letting go of a relationship that was one-sided from day one.

But in every bad situation, there’s a turning point. In every dark room, there’s a light. In every corner, there’s a chance to change. And for me, it came two weeks after I stopped responding to anything from Mr. P – even his drunken phone calls and messages – and gave myself a break.

Because while we all experience pain, we process it differently. Because while we all want to not be bothered when the other person doesn’t seem to be upset, you can’t release the pain if you don’t let yourself feel it – or in my case, write it. Because while love is never quite equal, everyone we’ve loved – be it for three years or thirty – affects us in someway, positive or negative. Because while our friends buy us a drink at the start of the end, we buy them drinks at the end of the end, thanking them for their patience with our stupidity and our ability to obsess, even months after the fact. Because while we want to be brave and strong, resilient and uncompromising, there is nothing that dies slower or more painful than a dream – especially one that involves someone you really cared about. Because while the wrong person can seem like the right, the person who matters the most isn’t the one who got away or the one who stays, it’s the person you are after you walk away.

There is no race to finish the moving on process or a correct way to go about it. There is no way to skip the anger and the tears, the late-night words you want to take back or the bed that feels cold at first, but grows warmer. You don’t get better at breakups the more you have them, and you don’t have any better luck or built-up tolerance to letting go because you happen to write about your personal life.

This time isn’t about Mr. Possibility, or how he misses me or how he doesn’t. It’s not about the fact he didn’t turn out as I had hoped or that I didn’t kick him out of my life sooner than later. It’s not about who moves on first or last. It’s not about the relationship that was or the relationship that I wanted. It’s not about how I feel right now, how I felt six months ago or two weeks ago. It’s not about how I’ll feel tomorrow. It’s not about the fact that it hurt – or that at times, it still hurts.

It’s about the fact that I’m letting myself feel it. And by feeling it, but forgiving myself for my tardiness and my endless optimism in love, I become a better me than I was before. While it may make me feel incredibly silly, naive and immature to have a broken heart that lusts after the past – it’s really not about how I feel, it’s about how I heal. Or rather, that I am.