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Should you text your ex before Yom Kippur?

It’s traditional to reach out and apologize to those we have hurt before Yom Kippur to ask for forgiveness. Does that extend to your ex?

Few relationships are as inherently intimate or emotional or painful as our romantic ones. While friendships run deep — and I think we would all be better off if we sought out friendships more deeply — who else are we more likely to have hurt, or been hurt by, than an ex?

Breakups lay bare the inherently strange social contract of relationships. One day, somebody could be the first person you call when your tire goes flat or your boss gives you a raise or you see a cute dog. The next day, it is all over. The person with whom you might have shared a bed, an apartment and a life suddenly has no social obligations to you at all, and you have no obligations to them. It’s weird!

Before figuring out whether or not you should text your ex, it’s important to examine where the impulse is coming from.

The temptation to reach out might be pious, but it is likely also just that: a temptation. The temptation to feel like a good person by offering another round of apologies; the temptation to revisit hurts in a religiously-approved moment; the temptation to showily take the higher ground, or reestablish contact with someone who has long ago lost interest.

If you miss them, want them back in your life, or are desperate for any way to be in touch — or hope that your apology will prompt them to realize they are the ones who are truly at fault — then you’re in a situation no Yom Kippur message, however beautifully crafted, can solve.

If you have broken up with someone this year, whether by choice or unwillingly, and find yourself asking, “should I or shouldn’t I text them before Yom Kippur,” here are three questions to consider before reaching out:

Why do you want to connect?

What do you hope to achieve with your message?

Do you — honestly — think your message will achieve this?

Maybe things ended poorly. You were callous or even cruel, and you want to let them know you are sorry.

Yom Kippur can be the right time to bring this up, provided it is earnest and you’re willing to truly own up to the way you acted.

But be clear with yourself. Do you want to ease their pain, or do you want to defend yourself?

Think about your message and imagine them reading it. Will it truly make them feel comforted, grateful or moved?

And more importantly, what conversation will the message prompt? It’s deeply not cool to write a long apology in order to get this whole mess out of your subconscious and then refuse to deal with any of the emotional fallout from the feelings you just whipped up. Don’t be a Yom Kippur coward.

If you do text your ex, then undertake the task solemnly and seriously. Send an email, not a text, with a clear subject line that will prepare the person for the contents, so they can choose when (and whether) to be emotionally ensnared.

If things are currently so sour between the two of you that you worry your name in their inbox might ruin their day, I’d consider sending an actual letter, either typed or handwritten, which gives the person even more control over when to read it.

In the letter itself, be brief but specific. Explain that you are sorry for how you treated them. Don’t worry about seeming too dramatic. Emotions seem more muted in letters, so spell it all out.

I wouldn’t outright ask for forgiveness. Lead with the apology, your understanding of your role in causing them pain and your deep regret.

If you are the wronged party, or you want to reach out to let the person know they are unforgiven, then I’d be even more cautious.

You don’t get a lot of shots to explain to someone that they are a terrible person who treated you terribly and should be wracked with guilt and horror, and so you want your message to be effective (and true).

Such perspective takes time and healing to deliver with maximum impact. For a more casual relationship breakup, there is no shame in a simple, “hey, there were some aspects of how we ended things that I don’t feel great about, and I’d appreciate an apology.” But for something more serious, and complex, I’d wait for the urge to vindictiveness to pass into an urge for self-knowledge.

Sometimes the urge is just to share your emotions with someone with whom you often shared intimate emotions.

And it makes sense: the High Holidays bring us back into family and community — and experiences we might have shared with an ex.

For recent breakups, Yom Kippur might prompt some healthy reflecting on the less than desirable actions that often are brought forth in these messy moments. But relationships have their own, internal rhythms of heartbreak and healing, and you don’t want Yom Kippur to mess with that process.

It is natural to think about exes during this time, and to miss them, and to feel guilt and tenderness and anger and sadness about the breakup. If you and the ex are in a really strong place, then you can share some of these feelings. Otherwise, think about who else in your life can be the person with whom you can now be sweet and sappy. You’ll need them going forward, anyway.

Shira Telushkin lives in Brooklyn, where she writes on religion, fashion and culture for a variety of publications.

To contact the author, email [email protected].


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