Now I've got my eye on another sales clerk. She works at the shop around the corner, my pop-in store when I need a wardrobe fix. After two years of dispensing fashion advice, she knows just the type of sweater I like. Definitely promising. But every time I build up the nerve to actually say some variation of "I need a best friend. You seem nice and might be able to get me a discount. Want to get a drink sometime?" there's another salesgirl with her, and I'm just not ready to deliver my first pickup line in front of an audience.

Approaching an unsuspecting salesclerk might be advanced friend-dating anyway, and I'm still in Friendship 101. But in just the first couple months of my quest, I've developed some hard-and-fast rules.

1. Facebook is your friend. The funny thing about social networks is that people you've met only once, people whose last names you may not even know, will request your friendship or accept your request. If you took a look at my list of "friends" in Chicago, you wouldn't believe I ever spent a moment alone. I'm Facebook friends with the friend of a friend of a friend I met at a birthday party last year, and the woman who sold me my wedding dress, and the girl I randomly made paella with in a cooking class nine months ago. In each case, we liked each other enough to become virtual friends, but had yet to take our relationship offline. My rule of thumb, which I offer to you, is this: If we can be Facebook friends, we can be face-to-face friends. To that end, the "Facebook message" system is a good one. If you hardly know this person, messaging via Facebook is less intrusive or—I'll just say it—less stalker-ish. When you've established a bit of banter, then you can start emailing directly. But to start, let whatever network connected you—be it Facebook, Twitter, LinkedIn, what have you—be the medium through which you establish communication.

2. Make the first move. Here's where finding a best friend isn't like dating. I know it's the 21st century and plenty of women are asking men out, but let's be honest, most of us are waiting for him to call. Men know this and usually take the initiative. But when two potential female BFFs are hoping to connect, then what? Who makes the first move? The answer: You. If you think she's the one, just call. Or email. Or Facebook message. Whatever. Just do something. Because we're all busy, and we all say "we should get together!" and we all forget to reach out, however much we really, truly, intended to. So stop sitting around waiting for her invitation. Shoot her an email. Five bucks says her response starts with "So good to hear from you!"

How to put yourself out there


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