Reb Golden- it is not our place to decide they shouldn’t be together. They have already met at your table and admired each other. Perhaps they can find a compromise that works for them. Maybe she will be inspired to become more traditional to support him. There’s a chance he will study harder in kollel so that he can find a job to support her afterwards. Or… maybe they will each follow their own path with a few simple agreements (no pants around his family), and focus on everything else that makes them a beautiful couple. Love makes people want to sacrifice to keep their spouse happy
Joseph- I have heard that a woman marries someone with her father’s personality, or a man marries his mother’s personality, but I can promise you that my children’s personalities are nothing like any of their aunts and uncles, and my nephews/ nieces are not much like me.