Dear Rosie & Sherry,

I hope you can help me. I'm a 36-year-old woman who has never been in a courtship (actually never more than two dates in a row with the same man). I had a difficult childhood, and adolescence filled with family tragedies. Since my family had its hands full, and was quite dysfunctional, I became self-reliant (emotionally and otherwise) at a very young age.

Despite these challenges, I think my life, in some ways, has been quite fortunate: I was an excellent student, graduated from a top college, and have a graduate degree. I've always placed a priority on joining nurturing communities, religious and otherwise, and have been able to contribute and offer leadership in return. I have filled my life with positive activities and positive people. My work life offers me a lot of flexibility and a lot of mental stimulation. And yes, past rounds of therapy have helped me understand myself, and why I have avoided marriage in the past.

So here I am, at age 36, finally ready to date and to love and to be loved in return -- and I'm terrified. I feel like I'm 36 going on 15. Topics of conversation that come up in dating -- e.g. getting married and having a family -- are an emotional minefield for me. I know not to dump too much on someone too soon, yet if I try to avoid answering seemingly simple questions (i.e. about my dating history), people will get suspicious.

How do I deal with my awkwardness and total lack of experience -- without revealing too much, too soon?


Dear Peggy,

First of all, we'd like you to know how impressed we are with the successful efforts you've made to overcome the challenges of your youth, and to work through the issues that would have prevented you from developing and maintaining a healthy and happy marriage. It seems to us that the only thing holding you back right now is the awkwardness you feel from a lack of dating experience.

You are terrified imagining how a date would react to your news that you've never had a courtship before. But the kind of probing questions you are afraid to answer are completely out of place on a first date. Or even a second or third one. They are questions that should be answered with a polite, non-judgmental statement like, "I try not to discuss my dating history with someone I'm just getting to know. I feel that's a topic to discuss when two people are much further along in the courtship." Chances are, however, most people aren't going to ask this sort of question early on anyway.

When the appropriate time comes to open up about your past, you might want to say something along the following lines: When you were younger, you avoided dating because you were afraid of emotional intimacy, until you decided that you didn't want to spend the rest of your life alone. You've invested a lot of time and effort in working on yourself, and you are looking forward to a great future.

We're sure that many more questions will arise as you proceed into the world of serious dating. We strongly recommend that you find a happily married friend or couple who will be willing to be your dating coach/mentor. Most older singles, regardless of whether they've been dating for 10 years or 10 minutes, genuinely benefit from the advice and perspective of someone who knows first-hand how to move through the courtship process and how to sort out what's important in dating from what isn't. Many dating mentors successfully guide a single friend from the first date through engagement.

We wish you a bright future and hope that you are able to get married to a great guy very soon.

Rosie & Sherry