Dear Rosie & Sherry,

For the past few weeks I've been dating a special young woman for the purpose of marriage. She's a very "private" person, and it seems to take her longer to open up about herself than some of the other women I've dated. While I don't want to push, I wonder when is the correct time to bring up more serious conversations, and what is a tactful way to do it.

We don't have a problem relating to each other on a casual level. We've even had meaningful discussions, but most of the time we've talked about work and "Jewish geography" topics. I want to talk about life goals, worldview, having children, spiritual and communal goals.

Our schedules are so busy that we're only able to go out once a week or so, and we exchange e-mails and speak on the phone a few times a week. It doesn't seem that we are running out of things to talk about, but the lack of more serious topics is starting to bother me, and I really need an advice on how to bring it into a conversation. Thank you.


Dear Larry

You are asking about a problem that many people encounter. A number of daters have no idea how to make a transition from casual talk to something with more substance. That difficulty can keep them from continuing the courtship, because they wonder whether the two of them are capable of talking about more substantial issues, and if they will be able to relate to each other on a deep level. Many times, instead of telling themselves, "Yes, I can go on one more date with this person," they conclude, "It probably won't work out anyway" -- and stop going out.

In your case, the fact that the two of you find it relatively easy to talk to each other about casual topics indicates that it is worthwhile trying to move this courtship forward. We have some suggestions for how to expand the depth and quality of your communication. These suggestions can also be helpful for daters whose initial conversations don't flow that well, but who nevertheless believe the courtship has potential because the other person is "in the ballpark" and seems to be "nice enough." Some people need a little more time to feel comfortable opening up about themselves, while others become more at ease after they are able to discuss a few topics they relate to well and feel more confident about their conversational ability

Forget about thinking of a "normal" timetable.

Whether you find it easier to talk together and want pointers on how to move toward a deeper level of conversation, or want advice on how to get past that initial awkward way of relating to each other, our first suggestion is not to worry about time constraints. Forget about thinking, "By six weeks we should already be talking about X," or "We only have another three dates before we have to make a decision about where this is all heading." Daters who feel they have to meet a timetable, whether imposed by social norms or by pressure from family, can give up on a promising courtship because they erroneously conclude something must be "wrong" when things are moving "too slowly." Of course, a courtship should be moving forward, but it isn't uncommon to get off to a slow start and only gain momentum after a while.

Purposeful Dating

Our next suggestion is to give each date a purpose. For your first few dates, you want to become more at ease with each other, learn about certain life experiences and acquaintances you have in common, and get an idea of each other's personality, sense of humor, and view of certain issues. It sounds like you did this, and that's a great way to start off. Now is the time to gradually learn more about each other's tastes, opinions, ideas and ways of dealing with life.

At the same time, your topics should be somewhat "safe" -- keeping you out of territory that is too deeply personal, painful or emotional. It will still be too early to talk about such topics as traumatic life experiences, strong emotions or thoughts that you struggle with, serious conflicts within your family, or your deepest fears, thoughts and dreams. Subjects such as these are very intimate, and shouldn't be introduced until a man and woman have developed a deep enough level of comfort, friendship and trust.

We suggest that before each date, think of a few different pieces of information you'd like to learn about this woman, and prepare a few questions or anecdotes you can use to introduce the topic. For example, to know what values are most important to her, you could introduce this by talking about someone in your family, or someone you know, whom you really admire, and explain what it was you admired so much about them and why. You can then ask if there is anyone she really admires, and ask her to tell you about them. This is a good way to segue into qualities you admire in other people, what kind of character traits you value, and whether there are any traits within yourself that you are working to improve.

Consider where you see yourself in five years.

As you get to know each other better, another point of conversation to consider is where you see yourself in five years. You can talk about the different paths that are open to you, what you'd need in order to traverse each one, what factors might influence you to change, which route you'd really prefer, and which you're more likely to travel. Your ideas about the family life you hope to have should be a meaningful part of these discussions.

You could also talk about:

• What friendship means to you; describe what it was like to grow up with your best friend, have a friend move away, argue with a friend and then make up, or see the nature of your friendships change as you matured.

•  Describe an experience that changed your life, and how it affected you

• What makes you happiest, what are experiences from the past that you treasure, what aspects of your life today bring you joy?

• What are your tastes in music, art, furniture, movies, books? What it is like to be wowed by a painting in a museum, or have a bauble you like to look at on your coffee table.

• How do you handle challenges, and what you've found to be challenging?

• What things make you frustrated or angry, and how you handle yourself when that happens?

• What would you like to do if you had a month off with no worries about finances, time, or geography?

Ask each other questions about the whos, whats, wheres, whens, and whys of each topic. Questions that require a narrative answer (as opposed to "yes-no") help the conversation flow. And remember that it is not necessary to talk about more than one or two "significant" issues on each date. You also want to spend time simply enjoying each other's company, having fun, and experiencing casual conversations. All this will help you develop a shared history, which is a key building block of emotional connection.

We hope that our suggestions will help you courtship proceed, and we wish you success in navigating the dating maze,

Rosie & Sherry