Every February I get the same question:
“Should I send my ex a gift on Valentine’s Day?”
Or should you stay in no contact?
If you’re here, you’re probably feeling that urge right now.
Pause.
Acting from anxiety on Valentine’s Day ruins more second chances than it creates.
Because what you do on this day matters more than you think.
The desire to reach out doesn’t mean you’re weak.
It means you’re anxious.
And acting from anxiety is what ruins most second chances.
I explain this in detail in the video above, but let’s walk through it clearly here too.
But first, let’s address the question directly.
“Should I send flowers to my ex girlfriend on Valentine’s Day?”
Or, “Should I send my ex boyfriend chocolates on Valentine’s Day?”
I understand that it comes from a warm place in their heart and a hurting place.
The thought process is that a gift or card on this romantic day could soften the heart of their ex and cause them to feel love again enough to hopefully want to get back together with the person they dumped.
There’s also usually a fear within the person in your shoes that if you don’t send a gift to your ex on Valentine’s Day that it will hurt their feelings and ruin your chances of getting back together.
In fact, if you are like a lot of my coaching clients who have asked me about this, you even feel that if you could pick the perfect gift or card that communicates your love, the uniqueness of the relationship that you two had, and/or that reminds them of you when they look at it that maybe that would endear you to them to the point that your ex realizes he/she still loves you (and wants you).
I get it.
In fact, I’ve been there.
It feels like it could work.
I can also tell you that a common feeling within a coaching client who asks about giving a gift to their ex on Valentine’s Day is that they think I don’t fully understand the connection that they shared with their ex or how close they were.
People in your shoes often think I just don’t understand.
I have been there in terms of thinking that my ex and I were so close that other people just couldn’t get it and that if I could just touch my ex’s heart in some way with a word or gift that it would get through to them and they would want to get back together with me.
I can tell you, however, from two decades in the relationship-recovery service that it actually does not work that way.
Why Valentine’s Day Makes Breakups Feel Urgent
Valentine’s Day intensifies loneliness and loss in a way that ordinary days do not. It creates the false impression that if you do not act right now, you will miss a once-a-year window to fix the breakup. That pressure pushes people to reach out emotionally, send gifts, or break no contact at the worst possible time. What feels romantic or necessary on Valentine’s Day often looks desperate or intrusive to an ex who asked for space.
In my post, “Does my ex want me to contact them,” and also in my post, “What is my ex thinking during no contact,” I explain that there are a few reactions your ex can have to you contacting them in any way.
Keep in mind that your ex broke up with you and has not reached out to get back together or meet up with you yet.
That’s what I am assuming is going on if you are reading this article.
Assuming that is true, consider what I have to say from twenty years of professional observation:
What Happens If You Send Your Ex a Valentine’s Day Gift?
After a breakup, many people unknowingly make moves that cost them ground. My Emergency Breakup Kit shows what helps, what hurts, and what often pushes an ex away.
1. They May Feel Pity — And Pity Does Not Create Attraction
At first, this feels like a somewhat warm response and better than nothing.
That is incorrect.
When you pity someone or feel sorry for them, it’s almost impossible to be attracted to them.
That doesn’t mean that we don’t feel sorry for someone we are attracted to or hurt for someone we find attractive who is going through a difficult time.
What I’m saying is that pity can’t resuscitate attraction.
If your ex broke up with you, emotional attraction (at least) has fallen.
No matter what excuse your ex offers, if your ex was emotionally attracted to you enough, he/she would do whatever it took to be with you short of going to jail and even then, they might just try.
I discuss this at length in my post, “Why did my ex break up with me?“
So if you haven’t heard from your ex, that emotional attraction is still not high enough to compel them to reach out.
I know that you hate to hear that and I hate saying it but that is the reality at the moment.
So if your ex’s attraction is low and you send them a Valentine’s gift, they could pity you, but what else is possible?
2. They May Feel Anger, Because It Reopens the Emotional Wound
Why?
Why would your gift of love cause a response of anger from your ex?
Your ex goes through stages after breaking up with you.
The first stage, as I talk about in the post linked to in the sentence above, is relief.
After that stage, or even during that stage, which might take a few days or a few weeks, if you reach out to your ex, anger can be their response.
The reason is because your ex thinks that he/she has gotten the difficult part (the hump) over with.
You contacting them makes them have to see again that they have hurt you.
That’s not an angle you can use to re-attract your ex.
It’s really not.
If anything, as odd as it might seem, your ex turns you into “the enemy” in his/her brain if you constantly remind them that he/she hurt you.
Your ex, at least at this point, basically wants to pretend that they didn’t hurt you or wants to simply not think about it.
I’m not justifying it.
I’m just telling you what is likely going on in the mind and heart of your ex.
And so getting a gift from you can make them feel like you are making them have to deal with the fact again that they hurt you.
With some people, that can make them really angry.
3. They May Feel Relief, Which Lowers Urgency to Reconnect
Is that a bad thing you ask?
Yes.
The reason that’s a bad thing is that you need for your ex to feel the loss or at least the potential loss that they could lose you.
“But if they broke up with me, don’t they already feel that? Why would they care?”
I knew you would ask that!
Actually, people become quite arrogant after they breakup with someone.
Even humble, good, loving people get an ego stroke from breaking up with someone.
It’s basically that your ex has pushed you aside.
In many ways, your ex feels above you even if they would never admit that.
Part of that arrogance is the permeating idea that they could get you back at any point if they really wanted to.
And so since your ex feels that, they don’t really feel the breakup.
Your ex feels like there is a safety net.
If at any point they decide they don’t want the breakup, your ex believes that you will be waiting on them and they can just send a quick text and get you back.
Even if your ex has told you otherwise, deep down they feel like they could get you back because your ex feels a sense of control.
Basically, the one who breaks up is in control because they are making the decision and you, as the person who was dumped, are at their mercy.
Or at least it certainly feels that way.
So in order to change that mindset, which if it continues will only help your ex to move on, your ex needs to feel at the very least that they could lose you.
Maybe you feel like you could wait forever.
Fine, though that’s not a strong mindset, I get it and it might take time for you to feel otherwise.
You certainly don’t want your ex thinking that, that’s for sure.
So if you send them something on Valentine’s Day, your ex will almost certainly be reassured that they can go do whatever and whoever, take their time, and that there’s nothing for them to worry about because you will just be waiting for them permanently.
Again, there’s all kinds of immaturity and ego in that but I’m just telling you how it is.
Valentine’s Day magnifies relationship dynamics, and anything that signals neediness or waiting tends to backfire more strongly on this day than any other.
If you are thinking about sending a gift to your ex on Valentine’s Day and are wondering if you should, my expert opinion is that you should not.
It will set you back and lower your chances of getting back together with them.
V-Day of all days is when your ex should feel the breakup and feel your absence.
Your ex needs to feel the consequences of his/her actions in order to want something else.
Stay strong and don’t send a gift to them on that day.
Your ex should no longer enjoy the privileges of being yours and that means that since they don’t want to be your boyfriend or girlfriend, they don’t get gifts on a day meant for lovers.
If you’re struggling with whether to reach out at all, you may want to read Should I Contact My Ex, where I explain why silence often works better than emotional gestures.
Common Valentine’s Day Questions After a Breakup
What if I ignore Valentine’s Day completely?
Ignoring Valentine’s Day is often the strongest move you can make after a breakup. By doing nothing, you avoid sending mixed signals and allow your ex to fully feel your absence on a day that highlights connection and intimacy. Silence on Valentine’s Day creates far more curiosity and emotional impact than a gift or message ever could.
What if my ex reaches out first on Valentine’s Day?
If your ex reaches out first, it’s important not to overreact or turn it into an emotional conversation. Respond calmly and politely, without bringing up the relationship or your feelings. Let them be the one to reopen the door, and allow the interaction to stay light so you don’t raise defenses or pressure them.
What if my ex is dating someone else on Valentine’s Day?
If your ex is seeing someone else, sending a gift or message almost always hurts you more than it helps. It reinforces the idea that you are still waiting while they move on, which lowers attraction and self-respect. In this situation especially, silence protects your dignity and gives your ex the space to compare what they have now with what they lost.
Additional Frequently Asked Questions
Should I send my ex a gift on Valentine’s Day if I want them back?
In most cases, no. Sending a gift often lowers attraction and reassures your ex that you are still waiting. Valentine’s Day is a time when your absence matters most.
Will sending flowers or chocolates soften my ex’s heart?
Usually it does the opposite. Gifts can trigger pity, guilt, or irritation rather than romantic attraction. Attraction cannot be revived through sympathy.
Can sending a Valentine’s gift make my ex angry?
Yes. Your ex may feel forced to confront guilt or discomfort about the breakup, which can lead to irritation or emotional shutdown rather than warmth.
Does a Valentine’s gift make my ex miss me more?
No. Missing someone requires absence. A gift removes mystery and reinforces the idea that you are still emotionally available on their terms.
What message does a Valentine’s Day gift send after a breakup?
It often communicates that you are still waiting and emotionally invested, which reduces urgency and makes your ex feel in control.
Is Valentine’s Day a bad time to contact an ex?
Yes. Holidays amplify emotions, and reaching out during them often increases pressure. Silence during meaningful dates is usually more powerful.
What should I do instead of sending a gift?
Do nothing. Let your absence speak for you. Strength and restraint create more attraction than gestures during emotional holidays.
If you truly want your ex back, you cannot afford to act on emotion. Valentine’s Day pressure has ruined more reconciliations than almost any other holiday. The difference between those who get their ex back and those who push them further away usually comes down to timing and restraint.
