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I like to wait and see if this person is someone I want to meet any of my friends or family, this can take me anywhere from several weeks to 3 months depending on how often we see eachother/ interact. If I still feel unsure after 3 months it's probably a good thing I waited that long in the first place, sometimes I don't pick so well.
When and where: A comfortable relaxed backyard bar-b-que, a group get together at a local comedy club, brunch with friends on a lazy Sunday. An afternoon of boating in local waters, something fun.