First of all, good job on taking Henry's feelings into account. That's awesome. I don't know Henry but I think any useful advice is going to be specific to him. For instance, I'm a guy but have a six year old female alter and we've run into similar difficulties. Whereas I'm extraordinarily logical, she's incredibly intuitive. So in our case, I've invited her to weigh in on potential dates. Her having input into the process has actually helped both of us - I make better choices and she feels a measure of comfort and safety because she knows she's being listened to and her opinion is being sought out because it's respected.

We also did some remodeling of the internal playroom that she retreats to during any intimacy.