Tips for pursuing a shy guy?

There's this guy that I met a few months ago, that I almost instantly developed a massive crush on, and am interested in getting to know better. We've seen each other a couple more times since then, always in a group setting, never really one on one. We have mutual friends who have informed me that he's pretty shy and somewhat skittish about relationships due to a previous heartbreak that they know nothing about. I'm interested in trying to spend more time with him, but I'm pretty shy, too, and have never been the pursuer before. I'm not sure how to approach the situation, but I'm positive I'm going to have to be the one to initiate things if I want to see if it could go anywhere. Any ideas?
Updates:
Well, I bit the bullet and asked him. He said yes to having dinner on Monday night, but it took him ten hours to respond to me. Should I be worried that it took him that long to come up with a 12 word answer?

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Most Helpful Guy

  • I would not worry if it took 10 hours... please do not feel the need for instant gratification. And don't think that it took him that long to come up with a 12 word answer.

    I remember I lost my phone and couldn't find it for 2 whole days and people thought I ignored them or something.

    Hopefully everything is going well so far!

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Most Helpful Girl

  • Just ask him out lol cuz he's shy so he's not gonna do it.

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What Guys Said 2

  • I would ask him out yourself.

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  • Just ask him out for coffee, glad to hear of a woman willing to be the initiator for once

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