I’M LOOKING for help on how to start dating, and I have to tell you, I feel really alone on this. There doesn’t seem to be much advice for people in my situation.
All my life, I was told by my parents and adults to focus on school, do well and not date. My traditional, conservative parents expected nothing but extraordinary achievement from me. Unlike most people in this day and age, I didn’t date anyone in high school or college. I’m 27, and I’ve still never had a boyfriend. I’ve gone on dates and I’ve had sex, but I have no idea what it means to be in a relationship. I get the unhelpful advice that “it’ll happen when it’s right,” and “you need to focus on you to be ready for a relationship.” But, that’s all I’ve ever done.
I got the good grades, I went to a good school, I have a good job, I make a good living, I am able to rent an apartment by myself in an expensive city. Guys seem to be attracted to me, and I get asked out, but it always stops after one date.
It seems easy for everyone else to find boyfriends, but when I go out with a guy, it never goes anywhere. I worry I’ll never find somebody, because I’m used to being extremely self-sufficient and don’t know what it means to compromise, which I’ve been told is a central part of being in a relationship.
On paper, I sound very independent, but I’m a huge people-pleaser, and I tend to fall into a submissive role when I date a guy. I say this because I think most women get this immature behaviour out of their system when they are young, but I never had that chance.
Thirty looms close, and it worries me I have the dating experience of your average 14-year-old. Between statistics showing I’m in the extreme minority for women my age, and articles about how hard it is for women over 30 to get married, I am at a real loss.

Sandy,
When we read your letter, two expressions of John Donne came to mind: “Miserable abundance” and “beggarly riches.”
You are smart, educated and self-reliant, but you can’t hold the attention of eligible men. Instead of acting smart on a date, you act servile. You truly possess beggarly riches. Why?
The obvious answer is neglect from your ‘conservative’ parents in one important sphere of your life. Good parents know that social development is as important as intellectual development. That’s why they actively oversee their child’s first dating.
Your parents are also the obvious explanation for your people-pleasing behaviour. We don’t know if it was both of them, or one of them with the permission of the other, but their plans for you lacked balance.
Perhaps their motivation was as benign as ignorance, or as damaging as manipulation, but they never found the equilibrium between freedom and control. Perhaps they never saw you with a family and children of your own, and lined you up as their nursemaid when they grew old.
Whatever their reasons, your parents handicapped you. It is as if they failed to give you milk or withheld fruit. Guys sense something is wrong, though they may not be able to say exactly what.
Any kind of deprivation is hard to overcome. We all want instant results, but lots of things, like growing up and getting an education, take time. Connect with an action-oriented therapist, one who will give you things to do. One of those first things will be redefining your role with your parents.
John Donne wrote, “Love, all alike, no season knows, nor clime, nor hours, days, months, which are the rags of time.” There is no reason to believe you cannot experience the love of which Donne wrote.