A little more than a year ago, he tried to end a short-term relationship that was moving too fast. He instigated the break-up but, much like Rebecca, went back to the proverbial well when he'd had a bit to drink.
He said he felt terrible when he realized what he'd done in the morning. But his regret stemmed more from a concern for others than from personal embarrassment.
"For me, it's more [about] not wanting to hurt somebody's feelings than it is [about] being stupid," he said, adding that those drunken e-mails extended a relationship past its prime because he didn't want to admit that he wasn't quite sober when he sent them.
But he emphasized that when it comes to work-related e-mail, he is extra-disciplined.
"My dad always said when you're at work, never send an e-mail that you wouldn't want your mother to see," he said. "I've heard too many stories about the one person who hit the dreaded reply all."
According to John Fischer, 26, a consultant with trend-spotting firm Infinia Foresight, more people should exercise that level of caution on the Internet.
Drunken dialing of the kind made famous by the movie "Sideways" can cause deep personal embarrassment. But, Fischer said, drunken e-mailing can be more significant and socially dangerous than the drunken indiscretions of yesteryear.
"What's interesting about e-mail is that it combines immediacy and indelibility," he said. "It's almost like these days the things we do online cast a digital shadow."
Electronic messages can go from being unknown to a viral sensation overnight, Fischer added.
In 2002, a 14-year-old high school student went from anonymity to Internet fame (and eventually to court) when a classmate posted a video clip of him wielding a golf ball retriever like a lightsaber online.
The video of the "Star Wars kid" was one of the most popular videos on the Internet in 2003 and made it onto CNET's 2005 list of the Top 10 Web fads.
In 2006, a Yale student named Aleksey Vayner achieved similar notoriety when an 11-page resume and video intended for the Swiss bank UBS made its way into inboxes across Wall Street and then YouTube.
Alcohol was not a catalyst in either of those examples. But, Fischer said, they show just how quickly curious news travels on the Internet.
"The skeletons that were once in your closet are now searchable on the Internet," he said. "We live in the age of the digital booty call."
Despite that reality, there's definitely a gap between people's ability to reach a huge audience and their awareness of this ability, he said.
While Google's new program isn't perfect, he said, it's a step in the right direction because it makes you stop and say, "Do I really want to send this?"
Judging from the attention Mail Goggles has received since its launch Monday -- blogs from Japan to Germany have been bursting with news of the program -- the Internet seems to agree that this is a well-intentioned feature.
But some of the people who might need it most question its effectiveness.
Pamela, a 29-year-old New York-based lawyer, told ABCNews.com that she'd been burned by her own drunken messages, but said texting -- not e-mailing -- was the bigger problem for her.
About a year ago, she said she'd gone to a party with a male colleague. When he left because she was too busy to pay attention to him, she let the messages fly.