In two parts of your letter, that second date with the woman who said she might want to have kids and this hypothetical first time of yours having sex, you're doing a lot of work imagining what things will be like for the other person. And in your first time sleeping with somebody, it's whether you need to get out in front of the possibility that it won't be good. This is not inherently bad or a mistake. I actually think this speaks to a really wonderful quality in you,. You're an empathic guy. But what I am appreciating is that sometimes that empathy and concern come at your expense or they create roadblocks where they really don't need to be any.

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