You are dating to learn more if he will be a good husband for you, not just a fun friend.
When dating, you are looking for a spouse. Someone to build a life with. Someone solid, stable, supportive, caring.
While fun and ‘cool’ are exciting to date, that is not the aspect that makes them great spouses.
During your dating, it is indeed important to confirm that you enjoy each other’s company and that you feel comfortable with each other.
You want to know that he ‘gets’ you and appreciates you -with all your human imperfections and quirks. And you respect and ‘get’ him. Can you be great friends?
You also share about values and visions for life (hashkafa). Are they similar enough? Can you respect and live with the differences?
Also important is to try to ascertain if he will be a good husband and father. Of course, he has not had the husband and father responsibilities yet, so you cannot simply look into that.
You can however have discussion about those areas. And learn about his mindset and thoughts about the roles of husband and wife, father and mother.
What makes a good husband for you is very individual.
Some women want to be the stay-at-home mother and homemaker.
Others want their husbands to be a very hands-on father and husband.
Others may want their husbands to spend all available time in Torah learning.
Others may want a simple lifestyle, where the husband may work less hours but be with the children more.
Listen to learn. Listen between the lines. Talk about it directly.
How does he talk about his mother, his sisters, his brother’s wife? What does he say about men (his friends and family members) and their roles in their family? What are his thoughts about work/ community work and family balance?
What was his experience growing up in his family? What were the roles of his father? His mother? Does he want to have a similar family dynamic? What does he hope will be different in his own family, and what will he proactively do toward that?
What are his plans for providing and taking care of his family? Does he seem responsible and capable? (In some circles, the young men are encouraged not to look for work until they are married; nonetheless, through conversation, you can often discern his attitudes toward the role of provider.)
Speak about your vision for family life. How does he respond? How do you feel about his responses?