Method One of Three

  1. Consider your motivations. No matter how you spin it, you are going to look like the bad guy if you break up with someone on Valentine’s Day. Think about why, of all days, you want to break up on Valentine’s Day, knowing that this will likely cause the breakup to be extra painful and may even ruin the holiday for your significant other in the future. Is this the precise reason why you want to break up on Valentine’s Day — because it will cause your partner the most pain? Or have you realized, through your preparations for the holiday, that you don’t really feel the way you would want to feel about your partner on such a romantic day? Before moving forward, really think about why you want to break up on Valentine’s Day and what the consequences might be.

    • Try to look through any anger or disappointment and think deeply about your motives. Maybe breaking up with your partner on Valentine’s will be very hurtful — but is this a move you will regret after some time has passed? Is this action really authentic to your character?
    • Though it’s best not to linger in a relationship when you know things aren’t going to work out, you may want to break with the person a week or two after the holiday. Or, even better, break up with her before Valentine’s Day, so he/she can return presents or cancel any plans he/she may have made for the two of you.
    • If you decide to go ahead with your plan, just know that you are not going to come off looking great by breaking up with someone on Valentine’s Day, so be prepared for some backlash.
  2. 2
    Think about why you want to end the relationship. Sometimes relationships just fizzle out. Other times one person cheats or is dishonest. In some cases, people simply aren’t compatible. Considering your reasons for breaking up can help you determine what to say.[1]

    • Some people initiate a Valentine’s Day breakup because things didn’t turn out perfectly from the moment the day started.[2] Don’t end a good relationship because of one day.
    • Although it may seem like you have a list of reasons, try to look for a common theme between them.
    • For example, if your significant other is pessimistic, makes fun of people, and depresses you, you can say that he is not positive enough for you.
  3. 3
    Reflect on your feelings. Even though you are the one initiating the break up, you might not feel good about it. Reflecting on your feelings will make it easier for you to accept the break up. It will also make it easier for you to explain to your soon-to-be ex. Understanding how you feel about the break up may help give both you and your ex closure.

    • Be honest with yourself. Don’t make up reasons why you want to break up to make yourself feel better about it.
    • Studies have shown that this is a common day for breakups.[3] But, figuring out why you are choosing Valentine’s Day to break up with your partner will help you determine the best time, place, and way to do it.
  4. 4
    Write down your main points. Since it is Valentine’s Day, you want to choose your words carefully, and in advance if possible. Having your main points prepared now may make it less awkward and strained moving forward.[4]

    • Think about how you will phrase your reasons. For example, “I don’t feel we’re compatible, so I’m breaking up with you.”
    • Plan to avoid phrases like “You always…” or “You never…” because they can make people defensive.
    • Prepare to talk briefly about the future. Take a few minutes to talk about how you are going to handle the rest of Valentine’s Day, letting friends and family know, and interacting with one another in the future.
  5. 5
    Rehearse what you want to say.Practicing will help you become more comfortable with breaking up on Valentine’s Day. It will give you the chance to practice what you want to say and how you want to say it.

    • Stand in front of the mirror and practice your delivery. Pay attention to your facial expressions; cultivate a caring, concerned expression, but also one that is focused, serious and firm.
    • Try role-playing with a friend so that you can think about responses to what your soon-to-be ex might say in objection.
    • Practice your delivery several times until you are comfortable with what you want to say and how and feel you are ready.

Method Two of Three:
Having the Break Up Discussion

  1. 1
    Choose the right time. Consider that at what time on Valentine’s Day you break up with your partner may have a big impact on how your break up goes. Weigh the pros and cons of breaking up as early as possible in the day, versus waiting to the middle or even end of the day.

    • Doing it early in the day may be the gentlest time on Valentine’s Day to break up. Going through the motions of caring for someone during Valentine’s Day can end up doing more damage than breaking up.[5] Also, this way your new ex will hopefully still have time to cancel any plans she may have made for the day.
    • Consider the end of the day. Breaking up with someone on Valentine’s Day morning might leave her (and you) miserable for the entire day. It also gives her the whole day to try to talk to you about it or out of it. This is an option, though remember that you should not go through the motions of being into the relationship all day and then suddenly give her the news at the end of the day. This may be a good option if you are both working all day and don’t have an opportunity to talk or see each other until the evening.
    • Rather than choosing Valentine’s day or night, think about both of your schedules to determine the best time of the day to break up. Considering what you both have on the agenda for the day will guide you in picking the best time of day to do it.
  2. 2
    Select an appropriate location. Unless you have absolutely no other choice, you should generally avoid breaking up via chat, text, email. It is impersonal and even a bit rude and disrespectful — especially if you have been together for some time. This is even more so the case on Valentine’s Day because of the romantic and sensitive nature of the day.[6]

    • Avoid romantic locations. You should also try to find somewhere that doesn’t hold any special meaning for the two of you.
    • Pick somewhere with privacy. Unless you have no other choice or you are trying to hurt or embarrass your partner, breaking up without an audience, especially on Valentine’s Day, is the best option.[7]
    • Places that may work include a community park, library, or any other public area that isn’t full of happy couples and big red hearts splashed throughout the landscape.
  3. 3
    Be honest. You want your soon-to-be ex to understand why you are breaking up on Valentine’s Day and also know that you mean business. Being honest with him about why you are ending it will hopefully help him accept the facts better and you won’t have extra explaining to do later.[8]

    • Although it may hurt him to have you say that you are leaving him for someone else, it’s better they find out from you than some other way.
    • For example, you could say, “It’s hard to me to admit this, but we’ve always been honest with each other. I’m breaking up with you because, over time, my feelings have changed.”
  4. 4
    Be respectful. Saying things you know will hurt the other person or causing a scene is not the best way to break up with someone, especially on Valentine’s Day. Don’t be mean or take shots at the other person’s character or personality, but be sure the person understands that you are breaking up with her and why.[9]

    • For example, saying something like, “I’m leaving you because you are lazy, ignorant, and annoying” is mean and hurtful.
    • Instead, you might try saying, “I’m not happy in this relationship anymore, so I’m ending it. I don’t think we are compatible and don’t see a future for us.”
  5. 5
    Maintain your resolve. During the break-up don’t allow the other person’s reaction sway your resolve. If you need to, recall why you wanted to break up with the other person and why you needed to do it on Valentine’s Day (and couldn’t wait until another day). Be strong. Even though Valentine’s Day is not the best day to end a relationship, remember that breaking up will ultimately be what’s best for both of you and that in all likelihood, you’re not the only couple breaking ties this holiday.