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They didn't even know they're married and rich, so I'm gonna say no, they don't meet regularly. They know each other, but I don't think they're truly friends. Besides, Leonard clearly said if she doesn't want him to do it, he won't.
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I'm not saying they are truly friends, but they meet regularly, not often but sometimes. Even once a year it's weird IMO, specially if Zack speaks all the times about Leonard and Penny to his wife.
Zack doesn't take a big part in Leonard and Penny's life but apparently they are very important in Zack's life.