Hey Liza, try this as it will work in opening up a conversation. You see him, he stares at you (you can even walk up and initiate this as it still fits). "Hi I'm Liza, I see you everywhere (list the places; park, street, etc..)." Then shake hands with him. Ask him what he is doing at the event, what he does for a living, and so on. He should open up at this point.
Don't walk right up to him if he is with his mates. Give him a second to split from them or maybe when there is only 1 or 2 with him.
If he is really shy invite him somewhere fun. "I think my girlfriends and I are going to be going to (insert place), would you like to come?" or "Next time I go to the park, you should come with me".
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Give him a window of oppurtunity and let him try
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Just go for it. If he is the shy type he might not jump on it even if it is there just due to his insecurity. No need to waste a good thing. Go for it! JUST DO IT!!! and let us know how it goes of course
