I think it would be safer and wiser to keep your professional and personal life totally separated. If money is your priority, focus on that and build your business up but try to totally avoid dating customers, more often then not it ends very badly (not in every case but in the vast majority). You sound like a nice person as well as sensitive (meant in the nicest possible way). There are predatory types that will sense your vulnerability and home in then take advantage of it. In this line of work, you must always maintain your guard and keep your defences up at all times.