"How can I attract Jill, so she'll agree to be with me?" is a bad question. It assumes it would be good for Jill to be with me. But how do I know that? I don't know her preferences in detail. Maybe I'm wrong for her. And I don't know her in detail. Maybe she's wrong for me.
"Who should I be with?" is a bad question too. It's just like, "Who should rule?" It focusses on making things a particular way and puts all the attention on figuring out which way to choose. Once made that way, the intent is that things stay that way.
A rational question is, "How should we set up a system of Government to best detect and correct mistakes, efficiently and non-violently?" And a rational question is, "How can I organize my personal relationships to best detect and correct mistakes?"
"Should I date John or Harry?" is a who should rule question. It's asking a question with long-lasting consequences, and trying to find the right answer once and for all. A rational approach is accept that we are fallible, and we make mistakes, and look for a way to proceed so that being mistaken won't do harm, or will do minimal harm, and a way forward so that mistakes can be corrected.
"Will you marry me" is a who should rule question. It's asking to permanently entrench a certain lifestyle. It's about committing to something for better or worse, not committing to seek the truth and correct mistakes whatever they may be. Marriage tries to put some things out of the reach of criticism and reason.
One theme of relationships is that they are on or off. People are dating or broken up. There isn't much middle ground. That conflicts with the gradual creation of relationships. Gradualness is important in all fields because it is best suited to detecting and correcting errors. By going one step at a time, and understanding what you're in for next, one can get a better idea of if the next step is indeed wise.
Another theme of relationships is to hide one's feelings until one is sure and has reached a final decision. Reasons are given for this such as fear of rejection. Whatever the reason, it has harmful effects. Hiding feelings means hiding them from criticism which could expose mistakes in them. Hiding feelings means hiding them from discussion by which one might learn something. Hiding feelings hides information that one's partner would find useful to know. And trying to reach a final decision is irrational because decisions shouldn't have finality; instead we should look to live in a way compatible with error detection and correction.