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How do I initiate a conversation with him

Published on August 10, 2013 by ds30

I have liked this former classmate from college for a while now, and he has recently moved to another city for work. I do not know what to do in order to maintain some sort of communication with him to see if this could go anywhere. We are both extremely quiet and shy and I have no idea if I should take the initiative to start a friendly conversation. Any ideas?


Dear ds30:

You've already taken the first step - See, wasn't that easy? You asked for help, so obviously this is an important matter to you. When you feel that pang but don't act on it, sometimes it takes a minor earthquake (or in this case a move) to shake things up a bit. In your case, the move prompted you to ask, should you make the first move.

Don't let yourself get caught up in who should ask first. Maybe you don't even care if you're the one to make the move, but you're afraid of being shot down, I'm not sure. What I am sure of is that if you feel for someone you're already friendly with, why let distance or first moves or anything stop you?

I wonder how many shy guys and girls never got together because no one made the first move? Well, don't you wonder - be his Facebook friend, or write him an email and just ask him how his move is going and how he likes the new job? You can say that something reminded you of him or that you were just wondering how he was. Keep it light and friendly (because best friends can make best lovers) and see how the conversation progresses. If you make the first move, the ball is in his court to step up and answer.

Once you both get over the initial "first chat" I bet you'll find plenty to chat about.

And on the off-chance that Mr. Shy Guy isn't your date-knight in shining armor, remember that that doesn't say anything about you, except that you took charge of your own dating life and made a move, and that's something to be proud of.

Either way it's a win-win for you girlfriend. So, put down your doubts and pick up that keyboard (or telephone) and start tapping away. Be short, sweet, friendly and upbeat - which is my rule for first dates, so let's just apply it to first-emails too.

Please write and tell me what happens - I really would love to know.

Thanks and good luck! ~LJ

LJ Innes is a YourTango Expert

He just moved to a new city for a job -- he would probably welcome a friendly email. I'd just email him and say, how is the new job? What's the city like? Did you find a place to live yet? There's so much to talk about, and he could probably use a friend. Do it!