A friend of mine (who wishes to remain anonymous in hopes of retaining a shred of his dignity) told me how he was recently rejected by a girl he tried to ask out over email. They had met in person through friends, and after a few emails he asked her out to drinks, and she politely blew him off. He wasn't sure what went wrong; he was sure there was a spark when they had met.
Our other friend gave an explanation: "she saw your Hotmail address."
This friend has had the same Hotmail since 1997 (it could be worse; at least its his real name @hotmail.com, not a goofy handle). Every time I'm sending him an email, I have a moment where I'm not sure that's really the right address. In fact, another friend of mine once IM'd me asking, "do you have [redacted]'s email? All I have is his old Hotmail address." No one thinks a young hip person could possible actually use such an antiquated method of communication.
I tweeted out asking if ladies would date a guy with a hotmail, and the response was overwhelmingly "no way". One woman replied simply with "🙅". My friend was shaken; he signed up for Gmail that night.
Is it superficial and stupid to judge someone based on their email address? Sure, but in dating, we make a thousand tiny snap judgements about a potential date: are they rude to waiters? Are they wearing ugly sneakers? Do they smell good? You can infer meaning from the fact that someone uses a weird out of date email service – this person is out of touch, stubborn, not tech-savvy or stuck in the past. WHY NOT judge them for this? It's just as legit as admiring their backside or taste in movies.