Dear Rosie & Sherry,

It's a pleasure to read your columns, and I value your thoughts highly. Let's see if you can help me!

I'm a 27-year-old male. As best I can tell, my dating troubles stem from a predilection for older women. I generally relate well to women a bit older than me, and things have generally gone well in this regard. Unfortunately, months or years down the line I run into trouble when the more serious questions arise. I have few qualms about ending my bachelorhood, but I am ambivalent about marrying someone older than me.

I am a resident physician, and, because of my crazy schedule, I do not see myself having children while still in training (which will be for a number of years yet). That said, I do want to have a family someday, and if at all possible a biological as opposed to adoptive one. I have already seen women in my field who have put off starting families, only to find that (even with fertility therapy) their chance for childbearing has passed them by.

The solution for me has been to try dating younger women. In recent months, friends have set me up with several younger women, and I've met others on my own or through Jewish dating networks. But I've found myself generally unfulfilled. I am happy to be meeting these new people, many of whom seem nice, but there's something missing. Perhaps it is an interest in core qualities?

I was a bit taken aback on a recent first date when a young woman confessed, "I don't usually let people set me up, but when I heard you had a medical degree and were tall enough that I could wear high heels, I said okay." Not sure how to respond, I complimented her on her shoes and tried to make some more conversation before returning to my menu.

The last few months, I have given a lot of thought to what I am looking for in a potential partner.I like women who are young enough at heart and aren't afraid to be silly once in a while. I also like depth of character. At the moment, I'm looking for a woman with the mind and spirit of someone a little older, in someone who is actually a few years younger. Does such a woman exist?

I would like to find a partner who has dreams and who will also support mine. I am attracted to women who are hardheaded enough to accomplish things in life and who are also somewhat visionary. Such qualities seem especially rare in the younger women I have met. With someone several years younger who I was recently dating, I tried to talk myself into it: "Maybe if I go out with her for a while, we'll 'grow up together' and we'll find common ground." In hindsight, such a notion seems better suited to theory than practice.

Taking stock of my prior dating experience, one of my friends joked, "At this rate, you'll still be chasing after the 90-year-olds when you're 80!" Now I'm confused how to proceed, and I've suspended my profiles on the Internet Dating Sites (which I'm forwarding for your review).

What do you think: Am I looking for love in all the wrong places?


Dear Gerry,

We've read your profile, and we have two suggestions that might help. The first has to do with what you are looking for in a marriage partner. You list a lot of vague, romantic qualities that we don't believe are very helpful to finding someone with whom you would want to build a lifetime relationship. We think you should throw out your "list" and make a new one.

To begin with, take some time to think about where you see your life going in the next six months, one year and five years. Don't limit yourself to what you hope to accomplish in your profession; think in terms of your marital status and family, how you would like to express yourself creatively and intellectually, where you see yourself spiritually, and what you expect in terms of lifestyle and finances. Once you think in terms of where you are going, you can look to date women who want to move their lives on a compatible path.

Then, think of 4 important qualities you possess that will make you a good husband. In addition, think of 4 important qualities you would like your future wife to possess. The qualities you have listed on your profile sound very romantic, but they evoke a movie-like image of romance. If you think in terms of qualities that would make someone a good partner for life, you'd probably revise most of what you're looking for.

Once you have clarified all this, try looking for a date whose goals are compatible to your own, and who has 2 or 3 of the qualities you think are important for your future wife to possess. It isn't necessary for someone to have all of them, because as you become involved in a serious courtship, you will probably find that the woman has other fine qualities you hadn't thought of, which more than compensate for what she didn't match on your "list."

Our second suggestion deals with your overall approach to dating. It's nice to see a guy who is very attuned to romance. However, if you are looking for a partner for life, you have to date differently.

People who want to find a marriage partner don't always realize that things need to develop over time. Movies and novels have conditioned us to expect that an instant connection will take place, but to be honest with you, that happens more in movies than it does in real life. Yes, there are some couples that hit it off from the start, but that is no guarantee that they are right for each other or that they will be able to develop a lasting relationship. Many happily married people say that their first date together was nothing to write home about. Yet they understood that the first date was simply an ice-breaker, and they gave themselves a second or third opportunity to get to know the person they are now married to!

We suggest that you don't go into a first date with strong expectations. Don't imagine that conversation will flow smoothly, or that the two of you will be filled with a glowing feeling. Don't even try to imagine whether this could be the person you will someday marry. Instead, think that you are spending a little time with a nice new person, and decide that if the date is simply "okay" (or better), you will go out with him/her again.

If the second date is a little better than the first, try a third date. After you learn more about each other, you'll be in a better position to see if your personalities are compatible. Remember: Whether you hit it off from the beginning, or whether it takes a few dates to ignite something between you, a serious courtship takes time to develop.

One more suggestion we think will be very helpful to you: Ask one or two happily married friends to be your sounding board/dating coach/advisor. Married people have the hindsight to be able to understand what is and isn't important in a relationship, and their perspective can be very valuable to their single friends.

Since you raised the issue of how long to wait to start a family, we also suggest that you talk to some married friends who have children. They can help you see how they juggled families and medical residencies, and why some found it doable and others more difficult. We know of some people who were able to have a child or two and complete a surgical residency and are happy that they did so.

These people may have had certain factors working in their favor, including their temperaments, financial ability to pay for child care and household help, help from the family, the demands of their residency program, and the manner in which their spouse shared family responsibilities.

When you see how others have made this arrangement work, you may be a little more open about the ages of the women you date. Good luck.

Rosie & Sherry