So there's this guy I want to get to know better, but I'm not sure how to :/ ?

Anonymous
My best friend has this friend she's been trying to 'get with me' for a while now (let's call him Tom). So Tom is a cool dude, with cool hobbies and cool friends, and I'm not so cool :P He started chatting me on fb a week ago and things have been going well, but to be honest, our conversations are pretty boring. We talk about what we did that day.. what we want to do tomorrow... what to do the day after... and not much more than that. I want to get to know him better and plan to hang out with him in person in a few days, but I'm not sure how to take this to the next level. I'm not so sure how to flirt on chat so I try asking interesting questions but I don't think it's cutting it.

In contrast, I just chatted with a new guy yesterday and the whole conversation was a lot of fun cuz we joked about all sorts of things. I'm just not sure how to do that with Tom :/ Help please?
So there's this guy I want to get to know better, but I'm not sure how to :/ ?
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