How do you transition from online friendship to real-life friendship?

Dear Starshine,

I have a friend who I've been talking to on Facebook, and he's really kind and funny. I didn't know him that well before, but now we're pretty good friends. The problem is, Facebook is the only place where we can seem to be friends. When we try to talk to each other in real life, we just stare at the ground and draw a blank. We could have a brilliant conversation online one night, and then find ourselves speechless in person the next day. I just don't know what to say to him. It's not like I can sit down at lunch one day and say, "OK, I'd like to know you better, so let's tell each other our life stories." I really like him, and I know he likes me back, but we're not going to get very far if we never interact. I can tell this is bothering him too. How do I break the ice?

The facelessness of online dialogue is seductive, ain't it? It invites us — even dares us — to type things we'd never have the guts to say in person. (As evidence, check out the comments posted beneath last week's Tough Love.)

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Communicating in person means having to gauge and respond to your audience's reaction — to see in their facial expressions when you've insulted them, to hear in their voice when you've disappointed them, to notice their body language when you've bored them. So it's no surprise that you're emboldened in front of the screen, and embarrassed in front of the guy.

But since you wrote to me about things you'd never tell a stranger face to face, allow me to respond with some things I'd never tell you in real life:

You're not speechless in person because you don't have anything to say to this guy. You're speechless in person because you're attracted to him and afraid that you won't, or can't, be as interesting to him in the flesh as you are on the screen. With Facebook acting as your flirtation conduit — the glowing, rectangular medium of your "brilliant conversations" — you have time to compose your thoughts and words. You can offer up calculated emoticons and breezy LOLs in place of genuine, heart-on-your-sleeve emotions.

But it's time to step out from behind the screen and show this guy you're more than the nimble fingers on the other side of his chat window. (Aren't you?) He's kind, he's funny, he likes you back, and he wants to interact with you in person — so he's worth a little discomfort. I recommend the discomfort take one of these forms:

1. Honestly, "I'd like to know you better, so let's tell each other our life stories" is a can't-miss come-on. What guy wouldn't be compelled to open up to you after that — or at least to laugh and admire your cojones?

2. Pick up where you left off with one of your brilliant conversations: "I was thinking about what you wrote last night and I remain unconvinced that Steve Carell is believable when he's playing an asshole. That will always be bad casting. Here's why …"

3. Throw a saddle on the elephant in the room and ride that beast to sincerity. Your instant-message man will be relieved when you say what you're both thinking: "Man, this is awkward!" Throw up your hands, have a laugh, and admit that you're tongue-tied when you two meet one-on-one.

Getting to know a guy offline is supposed to make you nervous and give you goose bumps. That's the fun part: locking eyes, exchanging smiles, holding hands. So go find out if you and your bashful pen pal have a physical chemistry — rather than just an internet connection.

Send me your dilemmas via email: ToughLove@TheWeek.com. And follow me on Twitter: @ToughLoveAdvice.