Ask Casey #1: Emailing My Ex

A new advice column. 

By copy casey



Thanks so much for doing this!

So, I’ve been pondering over reaching out to an ex of mine.

We went into no contact about a year and 2 months ago and I haven’t reached out since (actually I tried to email her a “hi how have you been” because she sent me her boundaries via email 😬 #goingcorporate).

Okay anyways, I really want to reach out not because I’m desperate but because I truly see her in my life. We align on a lot of values and she inspires me to be a better person. I feel like every time I’d talk to her I could breathe better because she’d just get me. You know. And before reaching out I decided to make a promise to myself. That I’d feel good by myself first, and then reach out if I felt like I wanted her, rather than needed her. I think that time is now, and I’m so terrified of making her uncomfortable because she’s the one who set these boundaries. She’s been very different since our relationship (and I respect that because people change and evolve 👏) but I still don’t know if there’s a specific reason to her acting extra cold towards me. Is she just trying to go cold turkey? Or is there something beyond that? Are there any suppressed feelings there?

I guess it’s weird to still feel this way but I want her to think that I’m a cool, fun, ambitious and all round good person so badly. I don’t want to walk on eggshells every time I think of reaching out. I want it to be simple, it’s so nice when it’s just simple.

Maybe it’s too early to say. But after our three year relationship, I feel like she’s one of the most important people in my life who I’d love to spend the rest of my life with.

So. If she set those boundaries. And said “see you in the future” at the end of the email, what do you think about me reaching out?

I’m not one of those traditional thinkers that go, “once an ex, never again” or some crap like that. I feel like two emotionally mature people can continue again and celebrate brand new versions of one another.

So. Whatchu think?


a potentially very desperate person simply trying to get over their ex but seeing this as a soulful connection that means more than it actually does 😁🥲

P.S. This is how she made me feel-

“It's that thing when you're with someone, and you love them and they know it, and they love you and you know it... but it's a party... and you're both talking to other people, and you're laughing and shining... and you look across the room and catch each other's eyes... but - but not because you're possessive, or it's precisely sexual... but because... that is your person in this life. And it's funny and sad, but only because this life will end, and it's this secret world that exists right there in public, unnoticed, that no one else knows about. It's sort of like how they say that other dimensions exist all around us, but we don't have the ability to perceive them. That's - That's what I want out of a relationship. Or just life, I guess.” - Greta Gerwig,
Frances Ha

Dear a potentially very desperate person simply trying to get over their ex but seeing this as a soulful connection that means more than it actually does 😁🥲,

After I gave my first blowjob, my then-boyfriend told me, “Not bad!” We listened to a Vampire Weekend vinyl record the whole time. He was my First Boyfriend, so I let him play whatever music he wanted. First Boyfriend always chose the music, the food, the activity. It terrified me to think I could ask First Boyfriend for anything.

That summer, I worked at a children’s science camp, and my little students often produced gadgets, drawings, and doodads. Almost every day, I would collect something the kids made so that I could give it to First Boyfriend. I would drive my parent’s car to his house, kiss him once he sat in the passenger seat, and hand him a twee mirror box made from cardboard that looked like it was put together by a third grader (because it was). He would thank me with a half-enthused “Oh, thanks!” and my heart would dry into a raisin. I kept bringing him more and more little gifts in the hopes they would make up for what I believed to be my horrible body, annoying voice, and insane hair. He (a tennis player and rock climber) had no business being with me (a goblin with an eating disorder).

The rest of the story unfolds predictably. First Boyfriend and I dated until we didn’t. It was a drawn-out, painful breakup in which no one left happy. I was heartbroken. I made a whole Tumblr page just for angry journal entries. I kissed other hotties of various genders. I attempted to forget First Boyfriend.

Years later, along came Second Boyfriend. So tall. Such thick legs. God/Flying Spaghetti Monster is good.

Sadly for me, I had not yet gotten over believing I was a hideous sea creature. You wouldn’t have known this from my general positive attitude, but deep down, like most of us, I believed I was a fraudulent narcissist with less-than-perfect teeth. Predictably, this caused problems for me and Second Boyfriend.

Second Boyfriend stayed around a lot longer than his predecessor. We never fought—not once—over the many years we were together. He brought this up a few times as if to say, “I don’t think we’re being real with each other if we’re not able to express frustration.” I would shoo those concerns away with a flick of my wrist, insisting to him that there was nothing to fight about. Why would he seek out conflict?

That relationship ran its course. We broke up. Again, I was heartbroken, not only because it was over, but because I felt like I never got close to him. I never let myself be seen because I was terrified that if I did that, I would lose the only person who I could con into loving me. I deeply believed that our partnership was an unfair bargain for Second Boyfriend, so I made it my mission to be as perfect as possible. It didn’t matter that he asked me, time and time again, to take down the walls. I refused to do it.

What do you think happened when Third Boyfriend rode into town? Can you make a guess about Fourth Boyfriend too?

The walls stayed up because I was sure Pandora’s box would unleash on these poor men if they came down. I couldn’t bear the thought of losing these boyfriends, but I also held the belief that if they knew me, they’d leave. The logic followed that they were the only ones who would ever let me trick them; no one in the future would be so gullible. The story would have it that they left anyway. I do not think my story is unique, but it is illustrative. When you believe that what you have is as good as you’ll ever get, you end up running on fumes.

I once had a friend describe romantic love as the Olympics of Being Alive; all of your weaknesses are tested until they either burn away in the bright sun of change or drown you in the sea of stubbornness. That metaphor is maybe a little harsh, but the point stands. You can’t expect to thrive in that kind of relationship if you’re running on an engine that doesn’t believe in its ability to be an engine.

Let me be a little more direct: when you say in your letter, “I feel like she’s one of the most important people in my life who I’d love to spend the rest of my life with,” I get worried that underneath your desire to have her in your life is the belief that she’s the only one who would be willing to be your partner. Even without knowing you, I know that belief is far from the truth. You’ve written a tender, funny letter, and that’s proof enough that there will be someone else. There always is.

Maybe I’m wrong and you’re not afraid she’s the only one. Maybe you’re an extremely confident sexual dynamo who just can’t get over this one previous girlfriend, but I get the sense she’s creating a bit of a hang-up for you. Are you dating other people? Are you taking yourself out to do stuff you like? Are you laughing at your own jokes? Are you buying new sex toys for solo time? Are you pursuing romantic and non-romantic connections with the splendid voraciousness of which your letter suggests you are capable? If the answer to any of these is “no,” then I beg you to try, if only once, if only for me.

What I love most about your letter is that you begin by clarifying that you’re not desperate, and then in your sign-off, you call yourself “potentially very desperate.” You also say you “want her to think that [you’re] a cool, fun, ambitious and all round good person so badly.” What if you’re already that person? Or, even more importantly, what if her recognition of those qualities means nothing? It matters less to me that you are or are not desperate; I’m more concerned about you living in fear of appearing desperate.

My friend, I do not think you are desperate. I think you’re a human being who happens to be having desperate feelings. In order to land that distinction, let me briefly take you into the wonderful world of etymology.

The word “desperate” comes from the Latin dēspērātus, which is the past participle of dēspērāre. That infinitive, dēspērāre, is made up of the classic de- prefix and spērāre, which means “to hope” or “to look forward to.” Put them together, and dēspērāre means something like “un-hope,” “anti-hope,” “de-hope.”

Put that infinitive state of un-hope into the past tense, and you get dēspērātus. We can then understand our modern English “desperate” as two things: 1) completely without hope and 2) fossilized, forever, in the past.

You, dear one, are not without hope or fossilized in the past. If you were, you wouldn’t have written me a letter. There is a part of you, however, that longs deeply for the connection you experienced with your ex-girlfriend. That part of you is the battery of your heart—almost literally—the thing that will propel you towards greater life. What an incredible gift it is to feel that tugging towards closeness that rings through you. That is not dēspērātus; it is precisely the opposite. It is humanity. It is sparkling, bottled faith from the mountain spring of life on Earth. I need you to trust—to be filled with MUCH HOPE—that there will be another lover (and perhaps multiple others) in your coming years who will provide you with the empathy and ease you long for. While your ex may have been the First or even The Best on your Game-of-Love Scorecard thus far, that doesn’t mean someone or something else won’t steal that spot. Lest you think I’m telling you, “There are other fish in the sea,” let me be clear: she might come back into your life! She might be the fish for you! But you will do both of you a favor by allowing her exactly as much space as she requests, even if it takes another decade. Think of the person you could be in the future if she does decide to return to your orbit—friend or otherwise. What kind of kick-ass, illuminated hottie will you be once you’ve spent that time reading the best books, smelling lilac bushes, cooking with garlic, and taking new, sweaty lovers? You can’t do any of that from your email drafts folder.

On a practical level, I do not believe you should reach out to your ex-girlfriend. Would she respond positively? Would she respond at all? I don’t know, but I hope you now understand why that’s beside the point. It’s beside the point because she is not your last opportunity at splendid, multi-dimensional love. You will have your Frances Ha fantasy, and not just with another romantic partner. Your friends, your passions, your family (whoever that may apply to) are on this Earth to open those precise dimensions for you. The sooner you stop deliberating over “to reach out” or “not to reach out,” the sooner you’ll be on the Yellow Brick Road to the very nirvana you think only she can give you.

I agree with you that “once an ex, never again” is juvenile. I agree that two mature adults can be friends after a break-up. I do think, however, that these things take time. A cliché, I know, but there’s truth there. She might need five years. She might need ten. You reaching out, especially since she was clear about her boundaries, will likely expand the amount of years she needs to be out of touch. A friend gave me similar advice once, shortly after First Boyfriend and I broke up, and it enraged me. She had no idea what the fuck she was walking about.

Except, of course, she did. I’m glad I listened because, after six years of no contact, I got a text from First Boyfriend. He had seen a picture of me on Instagram and thought I looked happy. He just wanted to reach out to say hi and that he hoped all was well. He was living many states away, so there was no ulterior sex/romance motive for his contact. We texted back and forth a few times, and that was it. It took maybe 180 seconds of my life, but the amount of closure it gave me was biblical. I’m so glad I didn’t try to facilitate our reunion because I would have wanted coffee. I would have wanted a FaceTime. I would have wanted a hug, of all things. What I got was so much smaller and so much better. I believe a similar closure is in store for you, but you may have to wait. In the meantime, it’s okay to have desperate feelings, just as long as you promise me not to go full dēspērāre.

The battery in your heart has a lot of juice left. Go find your Frances(es).

xo Casey


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