Should You Text Your Ex This Valentine’s Day?

I am nothing if not honest. Which is to say that while I am literally the author of an Enthusiastic Endorsement re: why you actually should text your ex on their birthday (for the plot), I am also a realist who will tell you that if you’ve found yourself wondering whether you should text your ex on Valentine’s Day, the answer is: “Oh, wow—absolutely not!”

Frankly, this is the answer to the, “Should I text my ex?” question all the time, every day, no matter what holiday it may or may not happen to be. (I wrote the birthday text thing in the immediate aftermath of a life-altering situationship, okay?) But on Valentine’s Day especially, there’s truly nothing to gain from it. Why? Because Valentine’s Day is the most obviously unhinged day to reach out to an ex-lover. There’s literally no way using this day as an excuse to text your ex is something you can play off as casual. While everyone knows what that birthday text to an ex is really about, there’s at least some pretense of, “Omg, totally just realized it’s your birthday. Just wanted to say hey!” Texting your ex on the day of love can mean literally nothing other than, “I am immersed in Tortured Poets levels of pining over you.”

Just as there’s obviously no good way to break up with someone, there’s also no good way to text an ex. But there are bad and worse ways to do it, and V-Day is probably the worst way (and worst day) to do an inevitably self-destructive deed.

At the same time, it really doesn’t matter what I have to say about it. If you’re gonna text your ex this Valentine’s Day, you’re gonna text your ex this Valentine’s Day. And honestly, the power to you. Life’s short; choose chaos. But might I suggest that if you found yourself asking this question, you may be looking for reasons to not go through with it? In any event, why don’t we at least take a moment to ask ourselves a few questions before pulling the trigger on that risky text, shall we?

1. When was the last time you did this?

Let’s pull up that chat history! Have you already texted this person to either lackluster or zero results? Let’s not get left on read again!

2. Can you just wait till their birthday?

Again, the texting an ex on their birthday move is also largely pointless and self-destructive. But! It’s at least a little less obvious than texting them on Valentine’s Day. A birthday text is more personal and can be more easily played off as a platonic “just checking in!” should things not go according to your probably delusional plan.

3. Why?

Actually though, why do you want to do this? I can’t answer that question! Only you and/or a licensed mental health professional can. But until you can schedule your next therapy appointment, instead of firing off that thirsty text, let’s just spend an honest minute (or several) considering what we actually hope to get out of this and whether or not those are reasonable expectations.

4. What if you just download a dating app instead?

Do you just require some level of validation to get you through this day? Same! Might I suggest simply re-downloading the apps? I know, I know—seems unhealthy! But, alas, it is also less unhealthy than texting your ex. It’s important to meet yourself where you’re at!

5. Will I have to un-block them on my phone in order to send this?

If you went so far as to program your phone so that it would deny you any sort of contact with this person, I’m going to venture to guess you did that for a reason. For the sake of your well-being (and your ex’s) and for that of humanity as a whole, you should keep this person blocked. And btw, this applies to Instagram and Facebook too.

6. Is there a chance I am currently blocked on their phone?

If you think there’s even a *chance* this person so desperately wants you out of their life that they blocked you from their phone, I hate to say it (read: secretly love to say it), but I don’t think a Valentine’s Day text is going to change anything for your couple odds.

7. Has their number been stored as some variation of “Do Not Call”?

And by variation, I mean: “Asshole,” “Why Are You Even Looking at This Number Right Now?” and/or “Go to Sleep and Do Not Look at This Number Again.” In other words, you didn’t go so far as to block them…but you have drunkenly tried to call this person so many times that you literally had to change their name in your contacts to an active reminder that you should not be speaking to them. Maybe that’s a sign that you should, um…not speak to them?

8. Have I been down this road before?

If this feels like déjà vu, that’s because it probably is déjà vu. Please spare your friends and family and do not put everyone through this emotional roller coaster another time. You can find another guy who buys you Cheetos. Promise.

9. Are they dating someone new?

There’s no shot their new partner sees your name light up on their phone and doesn’t want to rip both of your heads off. Buuut you already know that. As much as the thought of starting an unnecessary fight between your ex and their new partner on Valentine’s Day may seem appealing, just remember all that’s really going to happen is he’s going to block your number in front of her, then the two of them are going to laugh about the whole thing over a romantic Valentine’s Day dinner.

10. Am I dating someone new?

Maybe—and I’m just spitballing here—dump your current partner before making a move on your ex? I have a feeling that if you’re trying to spice things up with your ex on the most romantic day of the year, your current relationship isn’t exactly thriving.

11. Does this person even consider me a real ex?

Listen, I’m not trying to be mean here. I’m just trying to save you from mustering up the courage to reach out to the person you consider “an ex” and getting hit with a “new phone, who dis” from someone who never even bothered to store your number. Or worse, someone who has you in their phone as “Maybe: ….”

12. What am I hoping to get out of this?

Seriously. What are you hoping to achieve here? Are you thinking a rogue Valentine’s Day text is going to make you guys get back together? Are you hoping for a booty call? Are you just trying to get some attention because you’re bored and lonely? Whatever your hopes, make sure you get your expectations real low before going through with this. This is your ex we’re talking about, remember?

13. Do I have any desire to speak to them the other 364 days of the year?

I get it: It’s Valentine’s Day, you’re lonely, and suddenly everything reminds you of them…but this doesn’t mean you miss them. Go hang out with your other single girlfriends or call your mom. This feeling will pass.

14. How many drinks do I have in my body right now?

Hangovers are already horrific. Do you really want to add an embarrassing text to your ex to the list of things you’re inevitably going to be shame-spiraling over tomorrow? Didn’t think so….

15. Am I 100 percent sure this is still their phone number?

There are only two possible reasons for being unclear on whether or not this is still their number. Option one: You’ve had so many texts and calls go unanswered that you’re starting to wonder if it’s still really their number. Option two: You haven’t spoken in so long, you have no idea what their number is anymore. Either way, I’m cringing on your behalf and I really think you should not do this.

16. Would my best friend be cool with me sending this?

This is the most important question of all. If you’re nervous about telling your best friend that you’re even thinking about doing this, then you should probably NOT DO IT. While you might have this person on a pedestal, she sees them for who they really are. Trust her.

Alright, if you still feel good about sending the text after asking yourself these questions, then fine, I’ve done my part here. Deploy the text. But just for safekeeping, add these Qs to your Notes app so you have the goods on file should the time come (read: should your body become 60 percent rosé).