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Dating Advice #103 - Getting a Late Start
Dating Advice 103

Dating Advice #103 - Getting a Late Start

Already well into her 30s, she's now looking for her first serious courtship. And she's terrified.


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

January 19, 2003

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Visitor Comments: 6

(5) Anonymous, August 5, 2002 12:00 AM

feedback on your fears

I had my first serious relationship at age 32. Being over 30 is not "old".

If I met someone and learned that they had never been in a serious romantic relationship, it would probably make me wonder. As I think about this situation, it comes to me what I would want to hear from that person to make it less worrisome.

The details are not necessary. What you need to convey is that prior circumstances made it difficult (or unwise) to get into something longterm before now.

Or, you can shrug and say that you didn't meet the right guy and didn't want to get involved with the wrong one.

If you are now happy with your life, that is one of the most compelling attributes a person can have.

Not having had a prior relationship is not really a problem or some terrible skeleton in your closet. It will only be a problem if you let it consume you with worry.

focus on having a nice time out with the new person and deciding if you like him. Be yourself.

You are already doing a great job making the most of yourself.

Good luck!

(4) david morris, July 18, 2002 12:00 AM

diabilities creat no interest from women

I am david, I am 33 and was born with aspbergers, which is the highest form of autism. because of this mild social disorder I am unable to get any interest from any women at all. I am 33 but because of my handicap I appear more like 20-25 based on looks and experience in relationships, I have had very few relationships in my life and with very minor experience, I often feel no will ever have an interest back in me, there seems to be no interest from anyone at speed dating either, where do I go to eleminate the fear that I may be force to be single forever???

miriam, August 16, 2011 3:39 AM

You can try to contact Mr. Shaya Ostrov

Google him and you'll find him. He has helped alot of people. He will probably be able to help you or know where you can go to get help to find the right girl for a happy marriage.

(3) Anonymous, July 17, 2002 12:00 AM

We all have things that we would rather not discuss early on in a relationship

If someone were to hold it against you, then they are probably a closed-minded person that you would be better off without.

(2) Anonymous, July 16, 2002 12:00 AM

You're not alone!

I'm so relieved that I'm not the only one out there with a similar predicament. Thank you so much for your honesty and for opening up this question. Just yesterday I was on a date with someone and the conversation went to the inevitable past relationships area. I always feel like this is a big black minefield that I try and walk around, steering the conversation elsewhere. This doesn't just happen with dates, but also with interactions with acquaintances, co-workers, casual friends etc when the topic of conversation turns to dating, love and relationships.

I hate having to hide this side of myself, and to feel ashamed about my lack of experience in this arena, but somehow our society tells us that not having a relationship history implies that we are a failure, emotionally lacking, weird, not good relationship material etc, however well we might be doing in other areas of our lives.

I feel that when people talk about their past history, it's because they want to open up to us and share on a deeper level. To me, it seems like a normal thing for people to want to share about old relationships and I feel inadequate for not being able to go there with them.

I also hate feeling like I'm 15, when in all other areas of my life i'm double this age. It feels comparable to going to a job interview for a senior position, when you're still in kindergarten and thinking that scribbling with crayola will get you by. I think because most people have a long, involved history by the time they hit their 30s (either divorced, have lived with someone or have gone through a succession of long term relationships) it puts the power differential between us out of whack, as they are coming from a place of so much more experience than I am. And starting off a relationship with a feeling of power imbalance, doesn't feel good to me.

If anyone has views on any of the above (you included, Peggy!) I'd love to hear.

Someone once told me that we have to find the gifts in our wounds, so I guess it's all about owning our inexperience and our lives up until now, putting a positive spin on it and knowing that in the right kind of relationship this is something we'll want to share with our partners and it will melt into the background.

I wish you lots of luck in finding someone wonderful ! And I hope he comes soon !

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