There’s really no good day to text an ex. Thanksgiving, Christmas, their birthday, your birthday—these are all bad times to fire off a “Hey, how’ve you been?” to an ex, because the best time to text your ex is never. That said, there are bad times and worse times to do this ill-advised deed, and of all the holidays, life events, and lonely Friday nights when you might yourself tempted to reach out to a former flame, Valentine’s Day has got to be the worst day to actually do it.
Why? Because Valentine’s Day is probably the most obviously unhinged day of the entire year to reinitiate contact with an ex-lover. There’s simply no way to play it off as even remotely casual. A birthday text is bad enough, but at least an acknowledgement of an ex’s birth has some pretense of, “Omg, totally just realized it’s your birthday. Just wanted to say hey!” But texting your ex on Valentine’s Day, the day of love itself, indicates nothing other than, “I am immersed in Tortured Poets levels of pining over you.” Not a great look.
Of course, most people will probably tell you that you should definitely not text your ex and most of us have done it at one time or another. So the simple fact of the matter is: If you want to text your ex this Valentine’s Day, you’re probably going to text your ex this Valentine’s Day—regardless of what I or your friends or your ChatGPT therapist have to say about it. And honestly, the power to you—far be it from me to stop anyone from choosing chaos.
Still, if you’re here because you found yourself wondering (and presumably googling) whether you should text your ex this Valentine’s Day, it seems to me you may be looking for someone to talk you out of it. In which case, why don’t we take a moment to ask ourselves a few questions before pulling the trigger on that risky “Happy V-Day” 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 nonexistent results? Let’s not get left on read again!
2. Why?
Actually though, why do you want to do this? Before firing off that text, consider spending an honest minute (or several) considering what you actually hope to get out of this and whether or not those are reasonable expectations.
3. Will You Have to Un-Block a Number in Order to Send This?
If you went as 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 own well-being, you should probably keep this person blocked.
4. Is There a Chance You Are 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 don’t think a Valentine’s Day text is going to change anything. Best not to risk the horror of sending a blue text only to watch it turn green.
5. Is Their Number Stored as Some Variation of “Don’t Text Him”?
Maybe you haven’t gone so far as to block them, but if you’ve felt the need to literally change an ex’s contact info to an active reminder that you should not be speaking to them, that’s a sign you should probably heed your own advice.
6. Are They Dating Someone New?
Close your eyes and picture your ex and their new person laughing at your pathetic V-Day text together over a romantic dinner date. Does this still seem like a good idea?
7. Are You Dating Someone New?
If you’ve already moved onto someone new, don’t risk undoing all that work and potentially ruining a good thing just because Valentine’s Day has you feeling weird and nostalgic.
8. Does This Person Even Consider You a Real Ex?
This sounds harsh, but 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 “Who’s this?” from a situationship who never even bothered to save your number.
9. Do You Actually Miss This Person?
Or is it just Valentine’s Day? Feeling lonely or sad or nostalgic for a past lover on V-Day is normal, but it doesn’t mean you actually miss them. This feeling will pass.
10. Are You 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 they changed their number. Option two: You haven’t spoken in so long, you have no idea what their number is anymore. Either way, that feels like a number you don’t need to be texting.
11. Is This Something You’re Going to Want to Hide From Your Best Friend?
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 your ex on a pedestal, your best friend sees them for who they really are. Trust your best friend.
12. Have You Considered Just Downloading a Dating App Instead?
If all you really need is a little hit of validation to get through the day, might I suggest simply re-downloading the apps? It may not sound like the healthiest option, but it’s definitely less unhealthy than texting your ex on Valentine’s Day.
