Welcome to GS!
I'm not really very good at this, yeah? But I get what you're asking.
In my case, when I "take the reigns", I'm extremely direct. It can be very off-putting and make the other party feel awkward, especially if what they want to do is say "no".
I've directed Gid this way tho. Maybe he has some advice that will help.
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I think Mike's advice is awesome. Actually try out asking him out on a real date not just a meet up, something you planned, something special that allows you a little more time together without others there hovering over your conversation.
Also, if you've been talking online since the fall and have yet to move beyond casual chitchat and him being shy? You're probably not ready to actually jump into a relationship first. And I mean you as in the two of you, not you specifically. That might be your end goal, but it sounds a little early for that if you're both still tiptoeing around to explore where things are going to go.
I say try the date thing, try to get him talking a little more and just enjoy it and try not to push the rush too much.
I personally kinda dig the shy thing. It takes a little more time and effort, alot more patience, but you'd be surprised at what can be accomplished if you put your mind to it.
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You know, a movie theater isn't exactly private, but it is dark, and it gives you a couple hours to sit close and see just how interested you can get him into wanting to do something -after-
Or maybe a long walk in the park if the weather is cooperative. Somewhere off the beaten path maybe that gives you just a little privacy but not -too- much
And I would say a good venue is anything that -you- find appealing. Where would you like to be taken on a date? What would impress you?
Just relax and -enjoy- it, man. Half the fun of a relationship is learning about one another, the apprehension, the anxiety, the butterflies and giddiness of the brand new
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