There are some really great opinions here. Seems like everyone is hurting and really wants to help single girls and boys out.
Just to add my two cents. As a girl, I can really only speak for girls.
I feel that the ridiculously insane pressure for shidduchim is the worst problem. It pushes girls into a state of desperation, hopelessness, and despair that has to be seen to be believed. I’ve been there and its awful.
The only advice is to have meaning in your life that is only for you. If you hate your job but you’re doing it because you can leave at any time if you get engaged, then quit and do something you love. Go fun places, do fun things. Busy, exciting people are attractive. You will have something to offer, have what to talk about on dates, and present a picture of a unique and attractive individual that a boy will want to know more about. Also, if you have meaning to your life besides needing to get engaged as soon as possible, you will have a clearer head to make the decision to marry someone.
Also, think about money, if you want a learning boy you need it. If you want a working boy, you need it. That’s just the way it is. Secretaries and assistant teaching jobs don’t make money. You don’t have to be rich but you must have a plan.
I think it would be great if boys and girls could treat each other as adults. The initial few dates are just much easier and more comfortable with a shadchan in between. But after the couple feels mutual interest, they have to progress and treat each other as mature adults. Communicate directly, discuss where to go on dates, be mindful of the boy’s finances.w Don’t shy away from difficult conversations. Cover every topic as a mature adult and not a sweet aidel maidel who would rather her mother ask the hard questions for her. Life is hard and you need to know if you can trust this boy with your life and your deepest secrets. Just not on the first date, wait till later dates.
I know some people felt that girls should pay on dates because of….? So that they can show that the girl has money? So the girl can demonstrate her feminist side? So the girl can show that she can budget?
Let me pose to you then, boys. Would you like the girl to pick you up in a fancy car and then pay for the date? If it works for you go for it.
To my understanding however, most girls want to be taken care of by their husbands, i.e, taller, stronger, kills bugs for them. Girls wooing boys is counterintuitive and not what any girl I know wants.
Most of all though, I feel terrible that we are stuck in such a formal and costly system. Expectations are super high and extremely regimented and cause a lot of pain. Remember that you are a valuable person and that if the system is not working for you, you can change it. The shidduch system is not halacha, it is artificial.