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A Crash Course in Breaking Up like a Gentleman

Written by admin, Thursday, October 9th, 2008 in Dating Columns, Sex & Dating

Relationships come to an end for a lot of reasons. Perhaps something has come between the two of you or perhaps you just don’t feel the way you used to. Regardless of the reason, you’ve decided that your relationship needs to end and you’re going to be the one to do it.  Break-ups are messy and nobody wants to deal with them, but they’re necessary and it’s in everyone’s best interests (especially yours) to make them as clean as possible. To help you out with this, I’ve separated the break-up process into before, during, and after steps.


The most important thing for you to have as you approach the break-up is a strong sense of conviction. You have to know why you’re breaking up with him or her, and you can’t look back. By all means, it’s perfectly acceptable (and definitely encouraged) to try to work the problems out before you  decide that ending the relationship, but if you get cold feet halfway through the actual break-up then all hell is probably going to break loose.

After you’ve decided that you’re sure you want to end the relationship and you have a strong reason behind it, it can really help to roleplay the breakup with a friend. I know it sounds silly, but if you can predict your significant other’s objections and reason through them, it will make  the actual break-up process a great deal smoother.

You’re going to have to schedule a meeting in order to do the actual breaking up, and this can be tricky.  IMPORTANT NOTE: Yes, you must do this in person. You may not text or email them, and you can’t do it over the phone. Yes, it’s difficult to do in person, and yes, they’re probably going to burst out in tears, but hey, you signed on for this when you thought a relationship was a good idea. Break-ups are never fun, but think of it as the last part of the relationship, and you might as well do it right.

The difficult part of scheduling a meeting is that as soon as you ask him/her to meet you somewhere and have a discussion, they’ll see where you’re going and put up some defense. You can try to disguise your reason for a meeting with an “Oh, it’s such a nice day, why don’t we go for a walk in the park?” but they’re probably going to see through your plan. If they refuse to meet you then you’re going to have some problems, but try to coax them into it. It’s going to be much more difficult if you don’t.  This is the primary reason (and I’ll go into more detail in the next section about this) that I recommend their place as the ideal break-up location, because it’s a place where it’s easy to talk with them alone and doesn’t require them to go anywhere afterward.


The primary feature you’re going to look for in a potential break-up location is that the two of you are going to leave separately. If you have to drive him or her home afterward while they’re bawling their eyes out, it’s going to be a very uncomfortable ride. The location can be a semi-public place or a private one.  The middle of a crowded diner is probably not ideal, a park is closer to what you should be looking for.  Their place can work, as long as they don’t have any friends/family/roommates around, and is probably the best choice, as it allows you to immediately leave and they’re not forced to drive home while an emotional wreck.

At some point they’re probably going to ask if the two of you are going to remain friends. Your response here is completely your choice, but it’s difficult to say yes and convince them that the break-up is indeed final, and they’re likely to call you in the following days asking if you want to hang out “just as friends”. Inversely, if you say no, they’re likely to take the breakup even harder, but they’re less likely to try to get back together with you in the near future. Whether to remain friends or not is completely your decision, but on a purely pragmatic level I’d advise against it.

As far as the actual conversation goes, it’s best to lay it out pretty early, instead of talking for an hour and a half about whatever’s important in your lives and then dropping the bombshell. As far as actual phrasing, that’s left to your own discretion. Nobody knows the reasons as well as you, and it would be silly for me to recommend a specific line to feed your significant other.  The specific phrasing isn’t particularly important, but there’s three things you need to make sure you say:

1.  You need to tell them that you’re breaking up
2.  You need to explain why you’ve come to this decision
3.  You need to sound firm and convinced, and like you’ve thought it out (which you hopefully have)

A good example would be “Marissa, I’ve given our relationship a lot of thought recently, and I’ve decided that it’s not going to work out, because we have radically different interests.” Obviously, you’re going to want to substitute your own reason for the terribly vague one I’ve listed, but you get the idea. An important thing to note is that how difficult the break-up is depends primarily on the length of time the two of you have been together. This isn’t something you can change, so it’s best to simply plan for it.

After you’ve gotten your point across, there’s no point to sticking around to watch the carnage unfold, and it’s best to leave as soon as the two of you are done talking.  I’m definitely not saying to blurt it out, turn, and run as soon as you get there, but by the same token it’s not your job to help them plan the rest of your life as their new platonic best friend.


How easy the post-breakup will be is usually a direct result of how prepared you were for the break-up itself. If you were uncertain and stumbled over your words while doing the actual breaking up, s/he might think there’s a chance of the two of you getting back together and incessantly call you asking to “just go get lunch” or “just see a movie as friends” which are not traps you want to fall into.

As far as speaking with them in the weeks following the break-up, it’s probably not a good idea.  I advise against pretty much any interaction for at least a couple weeks, and if after those couple weeks you decide that you want to be friends, it’s much easier to sort out both of your emotions at that time. One or both of you will probably be very emotional immediately after the breakup, and it’s best to give you both time to settle down.

Final Thoughts

No one looks forward to break-ups.  There’s a reason they’re dreaded, and even with this guide, they’re probably still going to be unhappy experiences.  However, they’re also something you get better at as you do it more often.  I know that sounds terrible, but it’s the truth.  It’s not the end of the world if you have a bad breakup; you’ll learn something important and hopefully do better next time.  However, I hope this helps you avoid the biggest pitfalls you’ll encounter, and best of luck.

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One Response to A Crash Course in Breaking Up like a Gentleman

  1. Tyciol says:

    Probably a good way of avoiding being unable to stay friends is to avoid dating girls you can’t imagine befriending, right? At the same time, it’s hard to avoid seeing them as friends if that’s what you indeed do want to do. It makes sense to avoid this initially after a breakup since there needs to be a transition period, but inevitably there will be lingering feelings that you need to deal with when you do start seeing each other as friends afterwards.

    One thing I’m curious about, is how do you handle less emotional breakups, like are there cases where people break up and get together off and on based on changing scenarios in their lives, like moving for a job, another relationship ending, that kind of thing?

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