There’s a pivotal moment in an episode of “The Simpsons” that has always stood out in my memory. When Lisa tells Ralph Wiggum she doesn’t want to be his girlfriend, his face scrunches in agony and he clutches his heart as if it’s literally breaking. I remember giggling at the exaggeration and then years later when my own heart got broken, I put my hand to my chest and felt his pain.

While watching your buddy cry her eyes out over some unworthy jerk isn’t nearly as painful as getting the heave-ho yourself, it’s still difficult. Most of us want to help our BFFs through breakups, but what do you say? Or, more importantly, what shouldn’t you say?

Yesterday, 37-year old Helen Sun handcuffed herself to her estranged husband to keep him from leaving. Sun told investigators that she just wanted to talk—don’t we all?—and the only way she could get hubby to listen was by tying him up….

“So?” he asked me. “Is there anything else you want to say?”

To cut or not to cut an ex from your life after a breakup, that is the question. Just last week, a dear friend of mine had her divorce finalized after a long, drawn-out three year separation. Upon hearing that her now ex-husband wants to cut off all communication with her for the foreseeable future, she’s distraught. Over the course of their separation, they’d managed to remain quite friendly, keeping in touch with phone calls and texts, and even meeting up for occasional dinners out and seeing bands together they both loved. But now that the divorce is finalized, her ex says he needs time to process the ending of their marriage and to really close that chapter and move on. She’s devastated that she won’t have him in her life the way she has in the last few years and thinks he’s being unreasonable and even a little mean. I, on the other hand, think he’s doing what’s best for them both and that a little space will give them the kind of closure they probably could have benefited from years ago.

Breaking up is never a pleasant experience. The relationship moves from “You are awesome, let’s spend oodles of time together,” to “Actually, I’m not very fond of you, let’s never see each other again.” Tears fall, fists fly, hurtful things are said—and that’s when a breakup goes well. One of the most important things to decide when breaking up is where it will happen. The right place can help a break up go smoothly. The wrong place and you can wind up crying alone on the side of the New Jersey Turnpike. Not that that’s ever happened to me. In general, you’re looking for neutral territory, a transient place that will not hold the memory of your breakup. Here are four places to avoid and four places to go to have the dreaded breakup conversation.

A recent article from Men’s Health lays out 16 ways a guy can save his relationship with his lady, most of which are remarkably idiotic. While I agree that talking to your girlfriend rather than you best buddy about your relationship (#8) is probably a good idea, I’m worried that the other 15 suggestions are just leading men down long, lonely roads of cold shoulders and sexless nights. After the jump, a few of the so-called relationship-savers that sound especially destructive. 

How many people do you know who’ve been downsized? Terminated? Let go? Fired? However you word it, the result is the same: Bummer, dude! According to the Bureau of Labor Statistics, 4.1 million people have lost their jobs in the last year alone. (The current total is about 11.6 million.)

To add insult to financial injury, some of these firings are handled horribly. Workers report being locked out of their offices, escorted out by security guards, or being replaced by less-experienced (cheaper) employees. Frequently, those lucky enough to hang onto their jobs are asked to take on more work for less dough.

It got me thinking about how similar firing someone from their job is to firing someone from your life. So, I took a gander through a bunch of employment guides and found some resources that could prove useful in your romantic life.

After liveblogging four hours of “The Bachelor” over the last two days, it’s no wonder I cannot get Poo-Poo Bach (as he was renamed last night), Sloppy Seconds (aka Molly), and Melissa out of my mind. As a result, it inspired this week’s Thoughts From Guys On Our IM topic, specifically breakups, and how much effort a couple should put in to saving a relationship before calling it quits. As I wrote about yesterday, “The Bachelor” hit a little close to home for me (not in a crying way, just in a “oh, I can relate to that” way), as I felt like in my breakup, I was given the option of trying to save what my fiance and I had. But how do guys feel about how much time and effort they should put into trying to make things work? Or are they more likely to throw in the towel as soon as the going gets rough? Between yesterday and today, I IM’d them to find out.

Here’s a tragic story. Elizabeth and her boyfriend dated for about a year and a half. They had some pets, and some fights, and one day, sick of him being a total douchebag, Elizabeth kicked him to the curb. A few weeks later, Elizabeth’s ex came knocking, along with his hefty father, papers in hand. After he moved his belongings out of her apartment, he had Elizabeth sign the papers, and in her confusion, she didn’t pay much attention. Later, she looked at what she had signed, and realized it was a bill for every dime her ex had ever spent on her during their relationship, from groceries to Valentine’s Day presents. Of course this “document” would never hold up in an actual court of law, but Elizabeth was pretty sure it would make people laugh, so she scanned and posted it on a blog, where we saw it. All of this got us thinking—while the idea of actually compiling a bill and delivering it to an ex is ridiculous and laughable, we can’t help but think that’s there’s some stuff we’d like to charge our exes for. Actual expenses yes, but also pain and suffering too. After the jump, how much you could feasibly charge an ex, after a breakup.

There’s a short video making its way around the internet called “How To Break Up With Your Girlfriend In 64 Easy Steps” that satirizes the typical highs and lows of an average relationship so well and surprisingly succinctly, I’ve watched it no fewer than, like, 18 times in the last week. It’s not perfect, though, mainly because it’s completely from the guy’s point of view and because, well, 64 steps is a lot. Being the more efficient sex, we ladies can break up with our guys much more quickly. So after the jump: How To Break Up With Your Boyfriend In 44 Easy Steps.

When I told a friend that I was in break-up recovery, she didn’t hand me the name of her therapist, she lent me her “Sex and the City” Collector’s Gift Set. I had caught reruns of the show on the few nights I watched television outside of “60 Minutes” and “Frontline,” and while I loved the show for Samantha’s bawdy comments and Carrie’s commitment issues, every time I caught a rerun I learned the lesson that I needed. It became my modern-day version of the After-School Special, and I was hooked. So a month ago, between tears, I sat down with a glass of red Zinfandel, some dark chocolate, and started on all six seasons of its high-heeled wisdom.

There are Zagat guides covering everything—from restaurants, hotels, and nightlife to spas, shopping, and golf courses. Now, the guidebook company is getting into the relationship advice arena. The new New York City Dating (And Dumping) Guide offers suggestions for intimate bars, couple-friendly activities, and the best places to break up. Sure, you could end a relationship over the phone, but wouldn’t it be better if you did it in a place where you knew there’d be hot bartenders? We hope editions for other cities are soon to come. [Zagat]

How do you remember a relationship after it has ended? By letters sent? Photos from vacations? Recipes from desserts eaten together? In Important Artifacts and Personal Property from the Collection of Lenore Doolan and Harold Morris, Including Books, Street Fashion, and Jewelry (Sarah Crichton Books), author Leanne Shapton recounts the relationship, from beginning to end, between fictional characters Lenore Doolan and Harold Morris, through an auction catalog of items amassed during their time together. It’s compelling, yet heartbreaking, to see how they fall apart, as shown through notes, emails, gifts, books, photos, and clothes that are up for (fictional) sale at the Strachan & Quinn auction house. [$10.80, Amazon.com]

One of the things I love about being in a relationship is that my friend circle multiplies. But what happens to those newly formed friendships when the relationship ends? For example, recently two of my friends who were in a couple broke up and it’s been awkward ever since. Where we used to all go out together once or twice a month, now I have to split time between them, and I have the nagging feeling that I’m cheating when I hang out with one and not the other. After driving myself crazy for a few weeks (Do I talk about or avoid the subject? Partake in talk about the ex or awkwardly change the subject when it comes up?), I sought some advice on dealing with the joint-friends breakup—who keeps whom? And does it really have to come down to that?

Last night I had a drink (okay, we had three) with my ex-fiance’s mother—she had called me previous to her coming into town and has asked if I wanted to meet up. I hadn’t seen her since about three weeks before our initial break/split/whatever, when she had come to town with her husband to meet my mom and see one of the spots we were considering for our wedding. Throughout the break process she was very kind and as supportive as she could be, given that I was in the middle of a relationship crisis with her son. I think she was so kind and supportive to me because obviously she is just a kind and supportive person in general, but also because she had come to think of me as part of her family—that’s why I think our breakup was so hard on her. And on me.

Yeah, yeah, I know I said last week’s column was going to be the final Breakup Diaries post, but then something amazing happened and I couldn’t resist an update. Last week I wrote about how, despite having made significant strides in recovering and moving on from my breakup, my ex still was haunting me in my dreams. On almost a nightly basis I was finding myself dreaming about him, begging him for answers—clearly, the thing holding me back from completely moving on was just questions about what got us there in the first place. The unfortunate thing about those dreams was knowing that I may NEVER get the answers I was seeking. I could only hope the dreams would go away sooner rather than later. Which brings me to last night…

Dan and Serena, decided to get back together on last week’s episode of “Gossip Girl.” But Lonely Boy and S were in for a surprise when they found out that they are…RELATED. Sort of. Their parents had a secret love-child many, many years ago and the twosome share a half-brother. EEK!  Sure, their love runs deeper than Chuck Bass’ pockets, but this is an obvious reason to break up with someone, right? Because as Serena said, “it’s a little too hillbilly.” (And you know they don’t stand for that on Park Ave.) Instead, these two decided to stay together, for now, and make the best out of a redneck situation.

This does bring up an interesting point. No matter how deep in love you may be, isn’t there a point in some relationships where it’s time to breakup? Couples stay together out of convenience and comfort, but deep down you may know it’s just not working between the two of you. And if being related in some sick twisted scenario isn’t a reason enough to throw in the towel, here are five reasons to breakup, after the jump.

Recently, I committed the ultimate relationship taboo: I told a man who wanted to spend the rest of his life with me that I couldn’t marry him. Even worse, I broke off my engagement at a time in my life when many of my close girlfriends are blissfully picking out wedding dresses and drafting tender vows of love to their soon-to-be husbands. Welcome to your late twenties, ladies.

During my engagement purgatory phase, when I’d finally gathered enough courage to share my indecision with a few confidantes, I was met with a collection of theories on how I would know if my fiancé was “the one” or not. After the jump, find out why all the nuptial advice I got amounted to a load of courtship crap when it came to my relationship.

This is going to be my last Breakup Diaries column, I think. I feel like I’ve reached an end to the deep mourning process that is a breakup and with 2009 being a new year, I’m ready for a fresh start. While my mind feels ready for that, and my body too (thanks $527 make out!), my dream life apparently hasn’t gotten the memo. Since the breakup occurred, I’ve dreamed about my ex, in some way, at least every other night. And it’s starting to piss me off.