ames, reminds me of my cousin, that dated a girl for around 10 times, they had their issues that they spoke about and straightened out. He took her all over to get to know diff points of her character, out to eat, to arcades, to a painting expidition…and guess what when they got enagaged they were thrilled! One more guess, 4 weeks b4 the wedding the engagement was broken. You see, there is no perfect way, u need to follow the derech that u feel suits u, according to the rabbanim that u follow, and u need to beg Hashem that the shidduch u eventually decide to go with is ur true bashert.
P.S. My cousin has a couple of children now already, he got engaged to someone else, a doll of a girl. He only met her around 5 times!! He was also very careful during the engagement, upon the advice of his Rosh Yeshiva, not to speak or see too often.