41 and Never Dated – What Am I Doing Wrong?

Dear Neil:  I am forty-one and have never dated or even been asked out on a date.  I am a Christian, nice looking, successful and full of life and joy.  My question is why have I not been asked out or even approached?  To me, God has this glass box around me with a sign that says Don’t Touch!  I can only guess that I am giving some sign that says “stay away.”  Any help would be great.

Alone in Texas


Dear Alone:  If you have a glass box around you, it comes from something you’re doing, not something God is doing.  Perhaps you’ve unknowingly adopted a stance that you would rather be alone than risk getting hurt or rejected.

If you were unemployed, you would likely spend huge amounts of time and energy looking for work.  When you contrast that with the amount of time, energy and enthusiasm spent looking for an intimate partner, you may discover that you’re putting in a fraction of the resources, life force and focus you routinely give other important priorities in life.   If so, that becomes your first task—to go after the goal of becoming romantically involved with a man with more gusto.   Make a conscious choice to adopt a friendly, flirty, social presence around other people—especially men who attract you.  Don’t wait for others to reach out to you.  Reach out first yourself.

Your second task is to get comfortable in walking up to a man who interests you, introducing yourself, asking him questions about himself (such as his job or career, what sports he likes, what music, his goals, does he dance, what does he do for fun, etc.)  Then tell him something about you (I’m a photographer and I like to play tennis.  I’m interested in taking Tango lessons and learning more about football.)  Tell a story about your life, lessons you’ve learned, challenges you’ve faced, obstacles you’ve had to overcome—and ask him about his experiences as well.  Perhaps it would be prudent for you to not talk about religion in the beginning unless the man brings the subject up himself.   You must keep doing this until you get good at it.

Then I’d recommend you thoroughly explore how you avoid connection with other people.  What you do to keep yourself isolated, removed or unavailable from others.

People who are afraid to be known either don’t feel very good about themselves, fail to act interested in others or fail to personally reveal themselves.  If you have an attitude of defensive self-protection with other people, you are likely to go out into the world looking to keep yourself safe, rather than trying to get your social, emotional and intimacy needs met.  Thus, you won’t let your guard down long enough to connect with other people.  So your third task is to examine the possibility that you’re being too safe, too armored, too held back and too superficial around men, and therefore you’re not permitting a closer, deeper, more intimate connection.

Fourth, examine your emotions about not feeling worthy of a close relationship; your fears that if a man really gets to know you, he won’t want you—and will eventually reject you. Thoroughly explore your fears of being hurt, rejected, abandoned and betrayed.

Fifth, expand the people you are coming into contact with, by trying Internet dating, a dating service, a single’s group, a fan club meeting of your local sports team and adult education classes, to name a few places where you might meet new people you otherwise would not be likely to meet.

Finally, always look your best.  Dress femininely, and make sure your overall appearance is attractive and appealing and perhaps even a bit sexy.

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