Ex-etiquette: Exes and Valentine's Day

Jann Blackstone, Tribune News Service on Feb 7, 2025

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Q. Should I send a Valentine to my ex? What’s good ex-etiquette?

A. Each year I am asked this by literally hundreds of readers. I’m not sure why because the answer seems clear to me — but humans seem to be programmed by Hallmark, even if they don’t watch the channel. So, around about Feb. 14, we get nostalgic or romantic or both, and if we aren’t in a current relationship, the mind floats back to would-have, could-have, should-have, and the idea of sending a proclamation of love to an ex seems like a viable idea.

Here are some things to consider before you reach out to an ex on Valentine’s Day.

Once and for all, the answer really depends on your current situation and the dynamics of your past relationship.

Are you both single? If so, it might be a cool gesture. But if either of you is in a new relationship, it is bound to cause unnecessary tension.

What’s your goal? That’s the biggest question. Are you trying to rekindle something, apologize or just express that you still care? Figure out why you are even contemplating such a move and make sure your intentions are clear.

Was it a mutual and amicable breakup, or were there unresolved issues? Sending a valentine might bring up old wounds if things didn’t end well—or remind them that you are still out there. Again, we are back to examining our goal here. Do you want them back or are you just bored? Or do you just want to say hi? There are 364 other days to say hi. Valentine’s Day sends mixed messages if your motivation is not “love.”

Do you have children together? If you do be very careful about the message you are sending. Kids always want their parents to go back together. It will open a huge can of worms if they see a valentine from mom or dad on the refrigerator as they go back and forth between homes. Granted, you may think it’s a casual “remember when” gesture. They will see it as something completely different. If you are buying a valentine for your ex “from the kids” make sure that is evident—or get the kids involved in making or buying their own.

Anticipate how your ex might feel about receiving a valentine from you. Good Ex-Etiquette Rule No. 7, “Be empathetic when problem solving,” suggests you put yourself in their shoes and consider their potential reaction. If you know it will cause them problems, from interfering with a new relationship to manipulating old feelings just to humor yourself, don’t do it. If your feelings are genuine, why wait for Valentine’s Day? However, if you want that romantic reconciliation story — “Remember when I told you I still love you on Valentine’s Day?” — that day is coming up.

Ultimately, you know your ex and the situation best. If it feels right and you believe it will be received well, then maybe it’s worth a shot. If not, it might be best to keep those feelings to yourself or express them in a different way. That’s good ex-etiquette.