Vice City Pillow Talk: Unpacking the Dreaded "Hope You're Well" Text from an Ex

This is a public service announcement: If you've ever, after a long stretch of no contact, sent the nebulous "hope you're well" text to an ex, it's time for a citizen's arrest.

The same goes for "hey," "hi," "hello," or any standalone emoji sent at random. It's, at best, an insecure booty call and, at worst, a terrible mind fuck for someone on their healing journey.

It's vague. It's confusing. If you absolutely must reconnect with a former flame, there are other ways to do so, and it should be noted that this is a completely modern phenomenon. Thirty years ago, if you wanted to reach out to an ex, you'd need to pick up the phone, write a letter, or show up in person — all vastly more vulnerable options than a faceless shot into the ether.

Full disclosure: I've been on both sides of the ex-text (though not very often because my toxic trait is staying friends with all of my exes). My motivations for reaching out have been self-serving: seeking connection or validation after a bad breakup or just throwing a line out because I didn't want an empty bed. It was always selfish and caused more harm than good.

Why? Because breakups are traumatic. Some people eat their post-breakup feelings while others struggle to get food down; some become reclusive while others party around the clock. In extreme cases, the heartbroken attempt dramatic physical changes, like getting vaguely depressing tattoos or (God forbid) asking their hairdresser to give them bangs.

Even the most amicable splits are painful. When a partner shifts from being one of the most important people in your life to "somebody that you used to know," it causes major life upheaval (even if it turns out, as it almost always does, to be a positive change). That's why communication with exes should be clear, thought-out, and sensitive.

Dr. Carolina Pataky, relationship expert and founder of South Florida's Love Discovery Institute, tells New Times: "Before reaching out to an ex, it's essential to first delve into the introspective depths of one's motivations. What is driving this impulse to reconnect? Is it a search for closure, a nostalgia-infused longing, or perhaps unresolved feelings that refuse to be neatly archived in the past? Understanding these motivations clearly is foundational because it dictates the nature of the conversation and sets the tone for potential outcomes.

"Once you are clear on why you wish to reconnect, honesty and transparency become your guiding principles. Communicate your intentions with clarity — this is not just about making your thoughts known, but also about respecting the emotional and psychological space of your ex. This approach prevents misunderstandings and aligns both parties on expectations, reducing the potential emotional fallout.

"Additionally, timing is another critical factor. Consider where they might be in their life. Are they in a place where your contact could be welcomed, or seen as an intrusion? This is not just a matter of respect but of emotional etiquette, acknowledging that they, too, have moved on with their lives."

Dr. Pataky adds it's crucial to prepare yourself emotionally for all possible responses, including the most painful one: silence. The ability to accept this outcome is a testament to your emotional maturity and readiness to engage in this kind of delicate communication. It's about recognizing that reaching out, while cathartic, might not always lead to reconnection, and that sometimes, it must serve as a closure of its own.

I asked readers to share their ex-texting battle stories, and they didn't hold back. One woman told me that a former love reached out a year and a half after their breakup to tell her he'd always love and care about her. Two days later, he was engaged to someone else.

Other readers had advice to share. One noted they appreciate a tender and clear message from an ex, like "I miss us." Another was grateful to receive a sexy one that said, "I wanna swim in you." But my favorite advice, by far, is from the woman who received an out-of-the-blue message from a past lover "in a deeply horny moment," but ultimately decided instead to "masturbate and literally came to my senses."

Pillow Talk to Me: We want to hear from you. Send your dating wins, losses, and draws to [email protected].