Texting Your Ex Today Would Be Chaotic Evil — But Should You Do It Anyway?

Photographed by Anna Jay.
In the U.S., we have some pretty moronic “national days.” There’s National Bubble Wrap Appreciation Day. National Feral Cat Day, which just passed on October 16. But perhaps the most egregious of them all is happening today. It’s National Text Your Ex Day. Whoever came up with this “holiday” definitely had a penchant for stirring the pot.
I spoke to a few relationship therapists about this dubious day, and they all said that texting your ex is a bad call more often than not. Yes, there are exceptions to every rule, but, most times, you are not that exception (as we learned long ago from Gigi in He’s Just Not That Into You). “Overall, I would just say: Don’t text your ex,” says Moraya Seeger DeGeare, licensed marriage and family therapist and the co-owner of BFF Therapy in Beacon, NY. It's a recipe for drama, awkwardness, and anxiety, she says. Leave it alone.
On a logical level, there are about 1,246 things I’d suggest you do before you participate in this day. Adopting an actual feral cat is one of them. In the deepest recesses of my heart, however, I admit that I get the temptation to "paperclip" an ex — even though I know that's my "chaotic evil" side talking. I've been there, I've done it, I've regretted it, and I've done it again. So if you can’t shake the idea of pulling up their contact in your phone, I've got you: I asked my trusty relationship experts when it's okay to text an ex.
Every situation is different, so before texting, you'll want to do a deep dive into your motives to figure out why you want to reach out. Do you really just want to see how they're during during these ~surreal~ times? Or are are you actually trying to get back together, or sneakily see if they'd be down for a holiday hookup? Do you just want to drop that you're dating someone new? Or are you hoping that your new boo gets a little jealous when you mention you were texting your old flame, asks Damona Hoffman, a dating coach and host of The Dates & Mates Podcast.
Listen, these questions aren't flattering. But you have to know! If you've got ulterior motives, you may end up getting burned.
DeGeare suggests making a pros and cons list before sending that feeler text. Easy enough — but then she sneaks in this sucker punch: Also, check in with a friend before texting. Ideally someone who you confided in when you were in this past relationship, or going through the breakup. They’ll be able to give you a much-needed outside perspective. Genius, but evil.
You can also jot down why you broke up on a piece of paper or in the Notes app on your phone. Yes, do this even if you're just texting to "check in." This'll shake loose any sneaky "what ifs" that are rattling around in your heart. “A lot of times we romanticize relationships after they’re over,” says DeGeare. “Especially if you’re lonely right now during COVID-19. But it’s good to remember that there’s probably a reason you broke up.” 
If you're still fighting the urge to text, but you’re also feeling a lot of anxiety around what to say and about what the possible outcome could be, that’s a bad sign, DeGeare says. In that case, just let it lie.
In general, you don't want to text if you think you might be surprised by the response. If you haven't spoken since the breakup and you don't know how "over it" they are, why open Pandora's box now?
And of course, if one of the last things they said to you was, “I never want to talk to you again,” respect their wishes and delete their contact. You'd hope that your worst exes would do the same, after all.
All that said, there are a few situations where this text might not be the worst idea. If you ended things on good terms, it might be funny to send them a text that says “Happy National Text Your Ex Day! Hope you’re doing well.” It's also not the worst idea if it's been years since the breakup, and you've established a platonic relationship since. In that case, "a text is appropriate on a special occasion like a holiday or birthday, provided you are not trying to manipulate a particular outcome with it,” Hoffman says.
If this is you, it's best to go funny and specific over heavy or vague. In other words, no ‘what's up?’ texts, Hoffman advises. Instead, you could say, “Happy National Text Your Ex Day! There’s really a stupid ‘national day’ for everything, huh?" Make your motives and your expectations crystal-clear from the start. And if you don't ask a question, don't expect a response.
The one exception to the "keep it light" rule: If you're looking for closure. Perhaps surprisingly, DeGeare says you can text if this is your motive, as long as you're not too aggressive, and aren't asking them to have an hour-long conversation about an old argument. And just know it's a sensitive situation that can easily turn bad. Make sure you're not looking to pick a fight. Instead, be transparent and to the point: “It’s National Text Your Ex Day haha… On that note, I’ve always wondered why [fill in whatever loose thread has been bugging you], and I thought this was a good opportunity to ask you about it.” It’s a bold move, but if you think it will free you from a question that’s been taking up a lot of your mental energy, consider it. Just be sure you're ready to receive a non-answer — or stone-cold silence.
Finally, if you do text your ex and it goes horribly, go easy on yourself. You made the right decision for yourself at the time — or you tried to. Put in a pin in it, change their contact name to "DO NOT TEXT," and move forward. We're all doing our best.

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