Single & Suffering

I am 34 and have never had a boyfriend. I would like to be with a successful guy so he can love me enough to make me love myself. I have had a crush on a guy for 10 years, but I fear that he would see I am not fun enough, capable enough, or socially graceful enough. I can’t relax around successful men, and I come off as boring. As a child, my stepmom daily berated me for being lazy, stubborn, spoiled, narcissistic, dishonest, a slob, immature—whatever she felt like throwing at me. I now feel sorry for her. She just hated herself. I’ve never had a close relationship with her or my mom, whom I haven’t seen in 30 years. My dad is great, but we rarely know what to say to each other. Yes, I am a loser. Help!

There’s a difference between being a loser and being lost. Your stepmom hurled such an oppressive cloud of insults that she left no way for you to see yourself. It is a tribute to your generosity that you have mustered the compassion to forgive her. Your path beyond the continuing reach of her insults is to extend some of that same generosity to yourself.

Most people have an inner critic that judges them harshly in high-stakes moments, but yours is relentless. You spent a childhood being home-schooled in how to berate yourself. The negative thoughts that flood your mind about how badly you’re doing in social encounters come so swiftly they seem automatic and inevitable, but they are not. You were over-programmed by your stepmother to jump to those conclusions. It’s time to talk back—not to her but to yourself.

You’re right, however, to think that no successful guy is likely to fall for you—but not because you’re not good enough. It’s because you’re not comfortable enough with yourself. That, however, is remediable.

First, it might be instructive to consider why you’ve allowed yourself to stay stuck for 10 years on one man around whom you feel worthless, while imagining that he can magically boost your self-esteem. It’s called self-esteem because only you can do things that lift it. The only way that happens is by challenging yourself—doing some things differently, preferably starting with small goals. Even those will feel weird and risky at first, versus the comfort of the familiar, which is to keep the crush going another 10 years, at the great cost of your happiness.

A productive start might be to tackle the anxiety that robs you of yourself in big moments. Set as a first goal a successful conversation with your father. Ask him to join you for lunch. What to talk about? Ask him about himself—about his childhood, his favorite memory, or what he’s happiest about. Plan on bringing a smile to the occasion—and to every other social encounter; it puts people at ease and draws them out, so you don’t have to do all the heavy lifting.

Learn to sit quietly through silences; they can be very tender. They’re not signs of failure. Maybe you can arrange lunch or dinner with Dad once a week.

It can be helpful to lower your anxiety level before social encounters. People underestimate the contribution that physical activity makes to everyday mental states. Go for a 20-minute run before any event. You don’t have to be a runner. Just put on a pair of sneakers and go.

Another concrete step is to stop the rough self-evaluations in their tracks before they overtake your brain. Identify the people and situations that trigger you to turn against yourself. Prepare in advance to combat the litany of lousiness.

List all the positive things about yourself, create a note on your cell phone, and view it whenever you start slipping into negativity. Also, develop and silently rehearse a few strategies—things to say to people to carry you through difficult situations. Everybody has social gambits. Why not you?

Your belief that you need a successful person to validate you is not only wrong, it’s blinding you to more important qualities. Like kindness. People who treat you kindly are likely to have a great sense of themselves and to treat others well. You should seek nothing less in a potential partner.