Yated Shidduch Forum 11/29/19: Always Worried About a Family Situation. When Should I Share the Information?

Question:
I’m a single girl in my early twenties. Boruch Hashem, I get dates often enough. My dating has been fairly typical, with some mutual no’s, some good tries, and some “no shaychus” dates.
The thing is that I have a family situation. It is not something that has to do with me personally, and it is not something that most people know about my family. I’m finding that it’s holding me back from dating well, because I constantly feel like I’m on guard and like I’m hiding something. I am happy that boruch Hashem people don’t usually find it out when they check out my family and that my secret is safe, so to speak. But I feel like I can’t go much past the first and second date superficial conversations because of it. (I’ve dated boys four times or more, but it didn’t go anywhere.)
Sometimes I wish I can just tell on the first date so that I have a chance at open communication, but I was advised not to and I don’t think it’s smart, because then the boy will think of me as my family situation before getting to know me. On the other hand, I feel like a boy can’t get to know me anyway if I am so on guard.
Any advice?
Yated Shidduch Forum 11/22/19: Why Won’t the Shadchan Call me Back?

Question:
What can I do to get a shadchan to return my calls? I understand that a shadchan cannot return every call, but sometimes?
And why is it that my friend’s calls are always returned? On paper, there is no difference between our daughters. Both attended the same schools, both are bright and personable. Can the only difference be the perception that one father’s income overshadows the other? (One is a business owner, the other a salaried employee.) Could this be the case? What are middle-class people to do?
Thank you.
Yated Shidduch Forum 11/15/19: Am I Ready to Date?

Question:
I’m a 23-year-old boy and still don’t feel like I’m ready to get married. My parents tell me that I’m ready, but I’m unsure. Who’s right?
Yated Shidduch Forum 11/8/19: How Do I Cultivate a Meaningful Relationship During Dating?

Question:
In the dating process, how does one turn a superficial, casual relationship into a real, deep, close one? I dated someone for a while and really liked him, but my biggest concern was that our relationship was hardly deeper or more personal on the 7th date than it was on the 2nd. I felt that I did not know much more about this young man and there was almost no point in continuing.
One of the problems could be that I am a more private person, so I have a difficult time opening up and revealing my thoughts to others.
Any tips for the next time I go out?
Thank you.