Technology has brought wedding bells to many people’s lives, thanks to Web sites like eHarmony and Match.com. But technology also has had an impact on one of our most agonizing rites of passage: The break up. In the past, Dad let his girlfriend down easy with an ice cream float at the local soda fountain. Nowadays, a few terse words typed into an e-mail, text message or MySpace page can end a relationship faster than you can say “It’s not you, it’s me.”

Full disclosure: I am both a victim and a perpetrator of this impersonal practice. Several years ago I broke up with my girlfriend with an instant message (IM); a few years later, after going out again on a couple of dates, she returned the favor in an e-mail sent from work. Clearly, it was not meant to be.

This Valentine’s season, I sought out stories of others who—like Kevin Federline and myself—know all too well what breakups are like in the Information Age.

Return to Sender
Mattie Burkert, a 19-year-old college student at New York University, went out on two dates with Justin, who had just broken up with his longtime girlfriend. “I knew he was on the rebound, but we went out and it was fun,” Mattie says.

Until she got this text message after their second date: “Got back 2gether with my ex. Call me if you want to talk about it.” “What a jerk!” Mattie says. “When I did call him, he warned me that I might not want to go online for a few days, because his girlfriend had a jealous streak and had found my screen name. Apparently, she had a history of e-stalking girls he had dated in the past.”

“Luckily I was spared her wrath,” Mattie says, “but I lived in terror of AIM [AOL Instant Messenger] for the next month.”

IM Not In2U
Thankfully, I found I wasn’t the only one to have an IM breakup. AIM also played a role in the split between 19-year-old Californian Jessica Lee and her boyfriend six years ago. “One day his friend changed his online profile to say really profane things about me, and it really turned me off of my boyfriend and his friends,” Jessica says. “I broke up with him on IM—while his ‘away’ message was on. Horrible and juvenile and immature, I know.” Jessica adds that her boyfriend’s pal got back at her by writing a “big, rude comment” in her high school yearbook. “I don’t break up with people online anymore,” she says.