Personally, I think lip gloss could be a messy affair. But if you really wanted to wear it, I don't think he'd really care. I would wait until you two are alone, or separated from the group and then start to look him in the eyes. He will most likely look back and he will probably end up making the first move. Lean your head in and it'll just happen naturally. After the first one, you got nothing to worry about, good luck.
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