I am 25 years old, live in a big city, and would like to have a boyfriend. I have friends who go to social gatherings, bars, or clubs, but I can’t see myself in that kind of setting, and I also don’t see myself meeting someone through work. I am attractive but lack self-confidence. I am shy in groups. Of my friends who have boyfriends, they met them in college or grad school. I know many people who are in this position.

The obvious thing to try is website dating, but I am terrified. I have never tried to describe myself, and I could never put into words what I value in myself. It don’t want to feel like an object or a commodity. I hear stories of people who misrepresent themselves online and I would feel so vulnerable. My roommate got together with someone she met online, and after a few dates she learned he actually lived in a different city, was married, and had kids. It was a very bad experience. She is a very sensitive person, and has trouble trusting anyway, and I think I am a lot like that myself.

I know a big part of this is feeling ashamed. I feel like a failure because I don’t know how to go about this. Some people seem born knowing how to flirt but it’s not like I can ask someone to teach me this. My friends tell me that website dating is the norm now and I shouldn’t feel like a “loser”, but I still do. Do you have any advice for me?

Dr. J replies:

It can be difficult to meet potential partners, particularly in big cities.However, until you develop some confidence in your ability to read people socially, and until you develop the capacity to describe yourself and what you are looking for, you might want to wait until you feel less vulnerable and more defined as a person.
It is unclear if you want a boyfriend, or feel you need one to prove you are not deficient in some way. I don’t know if you want companionship and fun, or whether you are seeking deeper kind of intimacy. It may be hard to know this in the abstract. You are a young woman and this may be a time to cultivate your interests, your independence, and a career. Not having a boyfriend at the age of 25 does not mean you are socially inadequate, even if you would prefer to be dating. On the other hand, you do seem to portray yourself as shy, insecure, and perhaps lacking in life experience.

You might try making a narrative about your life and discussing it with a friend, or perhaps keeping a private journal in which you practice describing yourself. Notice what interests you and gives you pleasure. Do you have hobbies which you pursue on your own? Do you feel your impressions of other people are basically on target or in some way idiosyncratic? For example, do you feel most people are judging you critically or tend to dislike you?

When you are in groups, try to observe non-verbal communications as well as what people say and do…notice that people talk with their eyes and hands, as well as how they move their bodies. People are attuned to the physical distance between themselves and others, and people also choose where to place themselves in a room. Are they standing, sitting, lying down and so forth. How are they speaking… is it a whisper or too loud…is their language sophisticated or crude, simple or articulate and intellectual? Do they seem to be trying to create a particular impression? How are they dressed and does it seem appropriate? Do you attend to their facial expressions?

Do you feel people are interested in getting to know you? Equally important, are you interested in getting to know them? Are you so preoccupied with the possibility of rejection that it eclipses the possibility of pleasurable connection? People who flirt are skillful at using non-verbal communication to signal their availability or their sexual desirability. No one can teach you how to do this but your own powers of observation. However, some people smile and brighten when approached, and others frown or look blank. Do not underestimate how much these cues affect other people and signal your receptivity or aloofness.

There is no easy remedy for shyness, but sincere curiosity is very helpful. Pay attention to your own feelings and remember that if you are feeling vulnerable or concerned about rejection, there is a reasonable chance that the other person is feeling similar feelings. Most people are grateful if someone else can take the initiative in saying the first “ hello”.

With regard to using websites for dating, there is no question that it requires some savvy and experience, and an ability to use “personal radar” to pick up inconsistencies. Most sites allow for several weeks of email communication before setting up a place to meet, and be sure to meet in public places until you feel comfortable. Once you meet someone in person, you can usually tell fairly quickly if the relationship is something you wish to pursue. Exit tactfully but promptly if there is no chemistry. Be prepared to be patient and to screen many people… advantages of technology are volume and speed. In essence, efficiency.

Internet dating requires maintaining a balance between the wish to be pleasing and the wish to be pleased. It requires honesty and an alertness concerning the integrity of the other. Pay careful attention to reliability…frequent cancellations bode poorly for the future. If you can establish acquaintances or experiences in common, that is very helpful. The internet is a widely used tool, but certainly contains no promise of obtaining a boyfriend. While it may have had some stigma in a prior decade, there is nothing intrinsically demeaning about it. It gives you access to a broad range of people, without any guarantees, which is true of any social situation. It requires some balance between cynicism and optimism, and being prepared for some measured risk-taking.