It sounds like you just aren't comfortable with certain aspects of your relationships with these people and are well aware of that. That is a good thing. The only thing to do is to keep requesting what it is that would make you feel more comfortable and look for creative ways to achieve that that works for everyone involved. For example, it could be that an email mid way between the month would serve you better in regards to guy #2, whereas nothing from him just makes it too long a gap.
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