In my estimation, I’ve been dating—and breaking up—since I was 10. My first boyfriend was in the fifth grade, and I’m pretty sure he broke up with me by asking his friends to tell my friends that he didn’t want to do the Walk with Israel (a charity walk sponsored by the Jewish United Fund) with me. In my world, that was pretty harsh. I give that breakup a 10 on the rude scale.

In junior high, things became a little more complicated. I fell in love with my seventh grade boyfriend, the cutest boy in school. We dated for two years—until I found out I wasn’t the only cheerleader he was making out with at bar mitzvahs. I don’t think we ever had the break-up talk; I just stopped speaking to him (and those sneaky cheerleaders) once I found out about his PG-13 infidelities. That breakup gets a 9, since we never actually broke up. Heck, maybe we’re still dating.

High school brought a whole different set of heartbreaks. On one occasion, I found my junior-year boyfriend hiding in a mutual friend’s house with another girl; I literally caught them red-handed. He tried winning me back—and, pathetically, I took him back, more than a few times—but we could have saved a lot of time and heartache had we just broken up for good. I finally did so a couple of years later; he replied by telling me off in a letter. Rude scale: 5 (for the letter; 10 for the cheating).

Throughout college and beyond, I dated the College Beau, give or take a few dozen breakups: hang-ups, hysterical fights, the usual hurtful words. As emotionally draining as that relationship was, at least we had enough respect for each other to say exactly how we felt. So much so that he picked the morning of my brother’s wedding nine years ago to tell me he was never going to move to Chicago, and that marriage was definitely not in our future. I believe his exact words were, “I’ll never marry you.” The timing stunk, but the message was crystal clear. Rude scale: 10. (It was the day of my brother’s wedding!)

I’m no saint, either. I’ve definitely done some stupid things that I later regretted, like the time I had a guy come visit me, only to spend the entire week ignoring him once I realized I couldn’t stand the sight of him. (Rude scale: off the charts.) And I’m notorious for the tried-and-true “fade out.” Rather than look a person in the eye and tell him I don’t want to see him anymore, I’ve been a master of not returning phone calls or e-mails, and avoiding all contact whatsoever. Mature, I know. Or, worse, once I ended up pushing a boyfriend to break up with me because I couldn’t handle the emotional responsibility. What can I say? Confrontation is a bitch.

Breakups are never easy, but you can save your soon-to-be ex a lot of pain by handling the process with some shred of dignity, whether you’re the breakuper or the breakupee. Breaking up over e-mail or voicemail is definitely out of the question—and don’t even get me started on IM or text-message arguments. “I say be honest,” one married friend says. “I had a boyfriend tell me point blank: ‘I have the best time with you, but I don’t see myself ever loving you. I’m attracted to you, but you’re not my future.’ It sucked at the time but did wonders for closure.”

So, I polled a few friends about their best—or, rather, worst—break-up stories. Is there ever a good way or time to break someone’s heart? Here are some of their replies; post your own stories in the comments section below.

“I lost my virginity my freshman year of college to a woman who immediately fell in love with me,” Mark, 37, says. “She became increasingly possessive, so a few weeks later, knowing I wanted to date other people, I decided to break it off. Unfortunately, my lower half decided on one more ‘date.’ But later that night, I knew I had to say something. Suffice it to say, she was not happy,” he recalls. “Walking her out of my fraternity at two in the morning, we bumped into a friend, and she proceeded to kiss him goodnight—with tongue—right in front of me.”

Moral of the story: Don’t break up with a girl by having sex with her. Break-up sex should only happen once both parties are ready to move on. Trust me on this one.

“I went out with this guy, a Jewish mom’s dream, but for some reason he didn’t do it for me,” Susie, 30, says. “We went out a couple of times, and then I just ignored his last few calls. I found out a year later he got married. When I found out, I felt like I should’ve called him back. What didn’t I see in him that the new wife did? Why is it that guys always look better when they are with someone else?” (LGS note: Blowing someone off too soon can come back to haunt you, often in the form of revenge.)

“My ex-boyfriend and I were on the rocks before he went on a month-long trip,” Karen, 26, recalls. “He called from South Africa and e-mailed during the whole trip to make sure we were doing OK. When he came back, we had an intimate rendezvous, and then he basically stopped calling; we broke up later that week. I wasted a month of my summer waiting around for him.”

Some break-up stories are a little more shocking. “I walked in on a guy I had been dating for just over a month while he was sitting down, peeing,” Tracy says. “I stopped dead in my tracks and then quizzed him as to why he was sitting. He explained that he sits all the time—in public, too! It was just too weird for me.” Tracy ran for the hills and never talked to him again, but her karma came back to haunt her. “Then there was the time when the guy I was on and off with for five years dumped a drink in my face when I walked by him in a bar,” she remembers, laughing. Hey, breakups aren’t always so smooth—or dry.

What’s your worst break-up story? Did he move out while you were at work? Did she date one of your friends to get back at you? Post your comments below.