Well the thing about tripping is you can’t really predict what the result will be. I was able to realize I am cool and sexy because I have been doing a lot of work on myself to get over some past issues, and the trip just helped a few things click that I probably would have figured out in the next year or so either way. Success at dating is mostly about being comfortable with yourself, and that takes therapy and personal growth. If you’re doing those things, psychedelics can help make connections you are close to, but I would not think that any given trip is going to solve that particular problem if it’s not one you’re already making progress on.