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Timing Is Everything

Friends are great for giving advice, but when it comes to tough love, sometimes strangers are best. Learn more about when to break up with your SO from the 4-way panel.
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Dear 4-Way,
From your perspective, is there ever a good time to “break up” with someone? I’m thinking of doing it now, but I know she has a two-day sailing event she’s really excited about this weekend. No need to poop on it, I figure. If you don’t feel like being naked with someone again, I think that answers the question for you.—BN, San Francisco, CA

The straight man’s perspective: Chris Kennedy

When’s a good time to break up with someone? Before they break up with you… that way, you win!

No, seriously there’s never really a good time. Yes, there are definitely bad times to break up with someone: a death in their family, after she’s told you she’s pregnant, after he’s moved halfway across the country to be by you. Not good times. But worse than all of these is to want to break up but wait too long for the “perfect moment” to do so. The only “perfect” moment to take the train to Splitsville is the moment you know you need to break up.

There’s a Neil Sedaka song called “Breaking Up Is Hard to Do” and that’s true. I really like his original, elongated version of the song “Breaking Up Is Hard to Do… but Dragging It On and Putting Off the Inevitable is Excruciatingly Hard to Do.” Too bad that title was too long for the record label.  For both parties’ sake, do it as soon as you know and let everyone move on. You’re not doing anyone any favors by putting off the inevitable. Let her sail off without you. There are other fish in the sea.

The gay woman’s perspective: Jody Fischer

My friend, if I understand you correctly, your main reason for breaking up with this gal is because you don’t want to sleep with her at the current moment. Wow, I hope that I don’t ever have to date your sister. Excuse me for saying this, but how shallow!

Let me reverse the scenario for you. Do you want to date everyone you lust after? I don’t know about you, but I have found myself drawn towards some luscious lady “eye candy,” but I wouldn’t necessarily want to date them all. Keep in mind that I said date, not sleep with. News flash, sleeping with someone and dating are not necessarily synonymous. (That’s a whole other column.)  I wish I knew how long you have been “getting naked” with this woman. I would have to believe that you have been seeing her for a while, because you don’t need to break-up with a one-night stand. In a dating relationship, after that initial physical intimacy period, the “let’s have sex at every possible moment” phase morphs into a less frenzied pace. You get to know one another. And some of the things that you learn about your partner may turn you off. But I encourage you to stay with it and work through the tough stuff. Although new relationship sex is wonderful, longer term connections and passions can take you to new heights.

So go cheer her on as she sails off into the sunset, but don’t let that be the end. Unless of course she is just a nasty bitch, then, dump her now.

The gay man’s perspective: Darren Maddox

What are you going to accomplish by breaking up with her just before she goes out of town? Nothing! You’re not only going to ruin her trip, but also end up looking like a complete ass to all her friends who you may have a remote chance of hooking up with in the future. You’ll be dubbed the jackass. Even worse, if you break up with her just before she goes out of town, you’re not going to see or hear from her for a while and you’ll end up second guessing your decision because you’ll think she’s moved on. Do you really want to feel worse than you already do?

I say wait until she gets back. Maybe you’re one of those couples that just needs some space to remember how much you appreciate each other. Too many couples end up smothering each other and break up as a result. While she’s out of town, do some soul searching about what your life would be like if she never came back. She’ll have no idea you’re doing it and you’ll be able to make sure you’re doing the right thing if you do in fact go through with the breakup. One of two things is going to happen. You’re going to be so horned up when she gets back that you’re either going to rip her threads off or you’re not going to be able to fake it one second longer and you’ll want to pull your eyes out when she tries to jump on you. Either way, you’ll know for sure what to do.

The straight woman’s perspective: Rebecca Brown

The answer seems simple enough, but for whatever reason, this is really hard for some people. The best time to break up with someone is (and I’m all capping you so you can get a real feel for my frustration) WHEN YOU KNOW YOU DON’T CARE FOR HER IN THAT WAY ANYMORE. Granted, there are exceptions… like your girlfriend’s sailing event. I think it’s nice of you to consider the timing and her feelings and I think waiting until after it’s over is a smart move so you don’t ruin her whole weekend.

But the fact that you even have to ask “when” kind of makes me think you’ve got other issues about breaking up with her. Maybe you don’t like to be alone (hello, Jerry McGuire). Maybe you’re just not sure what (or who) is out there so you’re just hanging on to her until someone better comes along (hello, jerk). Or maybe you don’t like conflict (hello, human). That’s totally understandable. Breaking up with someone is hard. Most decent people don’t like being the cause of someone’s pain.

But understand this (and this is important, so I’m bolding it): you are not doing her any favors by staying with her. The longer it lasts, the more invested in you and your relationship she’s going to be. When you eventually reach your breaking point (no pun intended), the break-up is going to be even harder for her because she’s spent more time with you.

Oh, and about that “naked” business, I’ve got news for you, dude: in a committed relationship, the thrill of nakedness fades. If that’s all you’re basing your relationship on, I think you’re doing this girl a gigantic favor by breaking up with her. She should have the opportunity to sail in less shallow water.

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