Why is modern dating such a fucking minefield?

He is a serious musician who owns his own web development/marketing business. After many years of putting in very long hours and working a lot harder than I did by going to college and getting a day job, his business has grown to the point where he can put the bills on autopay, leave for a couple months at a time, and know it will be there when he gets back. He never had much of a social media presence in the first place (no LinkedIn to prevent competitors from stealing his client list) but he deleted his Facebook and only uses his Instagram to passively follow bands and the news, he never posts, and he spends a lot of his time as a hired musician for touring bands, playing gigs at churches, and playing at local shows.

/r/dating_advice Thread Parent