The Art Of Reconnecting: 5 Times It’s Okay To Text Your Ex — And 5 Times Really Please Don't

Before reconnecting with an ex, think about the consequences.

Last updated on Oct 27, 2025

Woman reconnects. Siamak Poorjam | Unsplash
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I was shocked to spy my old boyfriend's face pop up on social media in a group photo from a college friend's recent party. After he'd dumped me, I hadn't seen him in years. Ready to end the animosity between us, I private messaged him. He didn't answer. I felt rejected ... again. Then I realized I was fine with no contact. Why? Because I now had a great job, a sweeter guy, and was better off without him.

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Reconnecting with an ex can be fraught. After re-meeting my five worst breakups of all time to find out what had gone wrong and publishing a novel about a former boyfriend who snubbed me in public (pretending he didn't know who I was), I've devised a code of rules on amorous reconnections. Whether it's to say hello, express remorse, or resurrect your relationship, consider re-calling your lost love if:

Here are 5 times it’s okay to text your ex:

1. You're compelled to apologize

If you treated somebody horribly and later wish you hadn't, it's never too late to say you're sorry. But a brief note via social media is much smarter than showing up at someone's home or work unannounced in the Nirvana T-shirt you stole from him.

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Keep it short and sweet, the way AA amends usually go. Say what you did wrong and what you feel bad about. "I'm sorry I left without explaining to you what was really going on. I never meant to hurt you, and I hope you'll accept my belated apology." Ask yourself if it's the kind of mea culpa you'd appreciate getting, and if so, atone away.

RELATED: The Psychological Reason We Obsessively Text People Who Ignore Us

2. You have big news

woman who wants to text her ex as she has big news antoniodiaz / Shutterstock

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If you're about to wed, divorce, give birth, your parents are splitting, someone close died, or you're coming out or transitioning, you may want to share a major milestone with your former confidante. Perhaps first visit a counselor, clergy, or therapist to explore your expectations. (Making someone jealous is not a good motivation.)

Then, if you're compelled to give your ex an update, so they don't find out on Facebook, do it low-key. Try a short, innocuous letter, email, text, IM, or leave a phone message: "When you have time, I'd love to talk," and consider having coffee.

When I told one former beau that I was getting engaged, he emailed, "Congrats. Can I be your second husband?" That made me smile and almost erased the bad juju from our breakup.

Breakups can leave individuals with unresolved feelings, and sharing important news is a way of testing the waters or maintaining a connection. Research has shown that your brain might still crave the dopamine rush that came from connecting with that person, which can drive you to reach out.

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But make sure not to spill your gut-wrenched confessional poetry in a long, heavy, emotional drunk text, or reach out at midnight on Valentine's Day.

3. You can handle a brash brush-off

When I asked my high school boyfriend out for a drink to talk about what happened in our past, he emailed, "I'd rather take out my own appendix with a bottle of Jack and a dull spoon." Luckily, I was in a good emotional space, and stole his line for a laugh in my book. But it did hurt my feelings.

You may learn that your ex is now living blissfully with a woman who's smarter and cooler than you are, is still angry, or wants nothing to do with you. So if you email him, expect nothing in return. Plan dinner and a double feature with your best friend and turn off your iPhone so you don't check your messages incessantly.

4. You're finishing old business

My friend Amy was always bothered that she'd never returned the money from selling the engagement ring her ex-fiancé had given her. Though she assumed he was now blissfully wed and well off, she finally sent him a check with a note explaining the debt. She was surprised to learn his wife was ill, and he was appreciative of the money.

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This is related to the Zeigarnik effect, which describes the tendency to remember uncompleted tasks more easily than completed ones. In a breakup, unresolved issues can feel like an incomplete task, keeping the relationship mentally present until it's finished.

In my case, an ex-boyfriend recently asked to borrow $250. He'd been generous when I was a broke grad student, so I obliged, calling it a gift. He wrote me a lovely thank you. Weirdly, being able to aid him assuaged some of my guilt and helped us both.

RELATED: 9 Text Messages You Should Never, Ever Send Your Ex

5. You've never forgotten

Leaving the tearful phone message, "I'm still not over you!" is overkill. But if you're single and can ascertain that your ex isn't currently involved with someone, there are classy ways to reconnect without embarrassing yourself.

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My friend Michelle sent a nice holiday card to the fiancé she'd left in grad school, writing the line: "Truthfully, you're the best guy I've ever met and I still think about you." He called her, and they wound up married, long after their original broken engagement. On the other hand, never revisit your romantic history when:

Here are 5 times really please don't reach out to your ex:

1. Someone close to you is tying the knot

Feeling lonely or frustratingly single while having to be a bridesmaid at a friend's wedding isn't a good reason to relocate your last lover. This impulse is based on jealousy or competitiveness (externals), not an authentic longing for someone special and specific.

A wedding is a life-cycle event that naturally prompts reflection on one's own relationships. One study suggested that breaking the 'no contact' rule, especially in a moment of heightened emotion, can reset the grieving process and delay your recovery.

It didn't work for Julia Roberts or Kate Hudson in any rom-coms, and it probably won't work for you either.

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2. You hear he moved on

woman who shouldn't text her ex because she heard he moved on Nicoleta Ionescu / Shutterstock

There should be a law that the dumper has to wait until the dumpee finds a more perfect partner. Unfortunately, that rarely happens. Seeing photos on Instagram of your ex, who said he wasn't ready to commit to you — now giving a ring to your replacement doesn't justify you texting him "What??," or DMing your hottest selfie to him.

I once wasted hours web-stalking photographs of my ex's gorgeous fiancé, who was quieter, years younger, and thinner than me — until a friend who stopped by ordered me to "Step away from that computer!"

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Instead, call your mom, sister, or bestie to freak out, swear, and cry with, without trying to connect with him. That's how you move on.

RELATED: 4 Things Your Ex Is Really Saying With That Oh-So-Casual Text

3. Everything is up in the air

When I just landed in Manhattan at twenty, I bumped into a hot guy I'd once hooked up with and thought: it must be destiny. More like self-destruction. A creep doesn't change his lines in a new location.

When your relationship status with an ex is undefined, texting can harm your emotional well-being by delaying healing, fueling anxiety, and preventing you from moving forward. Research recommends that you wait for your ex to define the situation, concentrate on your own personal growth and healing.

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Switching colleges or graduate schools, moving to a different city, or applying for jobs in different fields can be stressful changes that challenge your equilibrium. But lying on your back isn't the way to land on your feet. Try to be brave and independent for a while, instead of desperately booty-calling.

4. You just met someone new

The quickest way to sabotage a fresh start is to regress by returning to the relative safety of your past. Freud called it "repetition compulsion." I call it Ex-Traction.

I admit, right after I started dating the awesome man I wound up marrying, I had a last rendezvous with a loser who couldn't commit. I left his place feeling ill and forever banished him from my life, never mentioning it to anyone (until now).

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When you begin to date somebody with potential, it might feel weird and scary and make you want to escape. That's actually good; doing something different is always a little uncomfortable. Now's the time to de-friend and unfollow your ex, or you'll soon have two exes to obsess over.

5. Life sucks

After feeling rejected by your latest hookup or being scolded by your parents, teachers, or boss, isn't the time you need an instant gratification reunion with someone who could cause more damage. Ditto, if you've been drugging or drinking too much, screwing up work, school, your finances, or your internship.

Even if your ex is willing to hold you while you cry, re-latching onto somebody when you're a needy basketcase could create more problems than it solves. Instead of your old boyfriend, call a new therapist.

As my (happily married) shrink told me, "Love won't make you happy. Make yourself happy. Then you'll find love."

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RELATED: Why Texting Your Ex "Happy Birthday” Is (Usually) A Terrible Idea

Susan Shapiro is an award-winning journalism professor, has written for The New York Times, Washington Post, L.A. Times, Cosmo, More, and Marie Claire. 

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