Song- if your question is how do you know you’re ready to start dating? Then my answer from my experience is when you feel the pull to get married again. Personally for quite some time after I divorced I didn’t want to hear about marriage. You really have to feel comfortable enough to start. I must say though that after the first post divorce date I felt even more ready,so start when you feel you want to remarry? Yes, and you may feel more excited about dating once you start. I did.
If your question was how do you know you’re ready to marry the person you are dating? Then I’ll say the following: there’s really no difference in dating round one or round two at its core, you are meeting someone to see whether they may be someone you can relate to, talk with, enjoy their company, share common goals, have a liking for each other, physically attracted to one another etc. that what dating is all about isn’t that true? Obviously you may have priorities more clarified to you now based on your past experience and honestly when I got divorced I learned a lot about myself in a positive way, and I have a clearer picture of whom I’d like to marry. So, to answer this question: when you’ve met someone you really like and enjoy and they make you feel good about yourself and you feel like you want to see them when their not with you and this person shares your dreams and goals, then you’re ready to get married to this person.
I hope this helps you in you quest to find your zivug, may Hashem give you clarity in your search and to myself and all those in the same boat.