Gazing From Afar…
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There are 3 million people in Boston. Don't assume the person you think you missed a connection with saw you, let alone remembers you. Be specific! Name which train, which direction, the time, the street, the stop, the bar, their initials, hair color, eye color, embarrassing tattoo placement, the song that was playing on the Jukebox at the time... For God sake, people, be specific! You're trying to make the connection this time!
Focus on Them
You were wearing a brown jacket with beige trim and have black, slightly highlighted hair, swooping three inches to the left? That's great, but what were they wearing? You noticed them. How do you expect them to know you're looking for them if you can only talk about yourself?
Keep it short and sweet. Nobody wants to read a dissertation about the person you think you might have possibly made eyes at on the T. Get in and get out.
Pay a Compliment
You've been thinking about this person long enough to get on the Web and type something up, so take the time to make your compliment count. Most girls don't want to hear, "Your ass looked so damn fine." You are trying to get her to write you, remember? People tend to like words like "beautiful", “handsome”, "breathtaking", "gorgeous". If you're at a loss, check a Thesaurus [see also: dictionary.com].
This is your second chance at a first impression. Don't blow it with bad grammar. If you're too lazy to hit the Shift key every now and then, at the very least, make the effort to type out full words, write in complete sentences, and punctuate. And for God sake, stop screaming.
Yes, we know you'd love to talk to this person. We know, because you just spent (hopefully only) a couple sentences explaining who they are and why you noticed them. If you did a good job with this, it really isn’t necessary to reiterate that you'd love to talk. That is why you filled out the e-mail form at the bottom of the page.
Be Charming or Clever
Chances are good that they didn’t notice you the first time, but if you’ve done a good job describing them, and are charming, cute, or clever enough in your delivery, you still have a shot in hell that they might contact you anyway. And if they did notice you the first time, a little charm never hurt anyone.
We Talked, But I Was Too Shy…
What did we talk about? Mention something memorable you said, because the person you spoke with may have talked to a lot of people that night.
Our Time Has Passed, But…
If random spottings on the streets of Boston need specificity, it’s possible that it’s even more crucial here. Many people have experienced bad breakups. Many people are missing someone or are hoping they are missed. Vagueness is not endearing here. Use the person’s initials and mention at least one thing that only the intended person would recognize or know about. The downside to not being specific enough here is that everyone will think it’s about them, which brings us to…
Don’t Start a Conversation
You shouldn’t need to start an ongoing conversation in order to figure out whether or not you are the intended receiver of the missed connection. These can go on for pages, and are frankly annoying. Follow step one and you won’t need step two. If you are the intended receiver of the missed connection, there are e-mail links included for a reason. Use them.
I Gave You My Number, But You Never Called
This isn't a missed connection. This is tough shit.