How Do You Date When You Don't Feel Worthy?

Alias (DO NOT USE A REAL NAME!!): Worthy while unemployed? Comment: I have read this column enough to know to refrain from being socially inept, show blatant lack of self awareness and feeling sorry for myself. Here goes my best try. I am almost out of work for a year, previously being let go from a six figure job and having to move in with a friend to make ends meet.



I've had to take a cold hard look at myself and how I've handled relationships. I found that the men I chose to date before were ones who would fit into my busy schedule easily, would help clean and cook around the house and were overall impressed with how far I climbed the corporate ladder. They were always younger, I always made more than them and dominated decision making, i.e we always went to my family's for holidays. I emphasized that value in the relationship was dictated by who brought home the bigger paycheck. I was WRONG, I emulated my parents relationship and I'm done with that crap. Now though, I find myself back in the dating pool and intent on finding my equal however I'm doubting the value I bring now that I am in between career changes and feeling lost without direction for my life.


I tried making lists of what I bring to the table as a human being and I feel inadequate, as if I failed to develop myself and my emotional intelligence over the years. I was a corporate robot and went through the motions to collect a paycheck, foregoing passion for stability. I do have substantial hobbies and have travelled extensively yet I still crave a partner to share the experiences with. My greatest fear is that the best advice for me is to stay single for awhile so that I can feel totally at peace with who I am as an individual and will have to explore the murky depths of my codependent tendencies. I just need a cold, hard slap of reality to know if I should stop dating completely or buck up and be confident that I have something substantial and unique to offer in a relationship. I appreciate feedback so I can hear how I "show up" in the world.

Age: 34 City: NYC State: NY


When you live and date in New York City or Boston or really any metropolitan city, you learn quickly that people place a lot of value on what you do for a living. Cities like NYC are filled with status-conscious singles. Those people aren't looking for a partner so much as they're looking for someone they can brag about to their friends, peers and on social media.


You don't want those people. Anybody that rejects you because your life is in flux is doing you a favor. Anybody who doesn't understand or have sympathy for the various curve balls life can throw hasn't lived much of a life. They've played it safe and haven't gotten terribly invested in anyone or anything.

People get sick. They lose their jobs. They experience severe emotional or financial distress. That's called life. Anybody who hasn't experienced any of those things or doesn't know someone who has probably lives in an insulated bubble.


Neither your credit score, bank balance or IQ is a measure of your humanity and character. Good people know that. What most people care about is how you are handling these setbacks. Are you living outside your means? Do you seem unmotivated? Are you looking to be supported in some way? If so, then expect to struggle in the dating world. If you take ownership of your circumstances and are working to correct them, you'll fare better.


It sounds like you defined yourself by your job and by how much you earned, and now believe that's how everyone thinks. It's not. As you're learning, there's more to life than a corporate grind and money. Which isn't to say you shouldn't care about money, because obviously that's something we all have to worry about. You just can't let your confidence and happiness depend on it.

Many people like to wait until they get back in shape or pay off their debt or find a job before they make a sincere effort to date. Here's a secret: it's never the right time. There will always be something you want to achieve or fix or improve, but because you want something or someone specific. I used to think that if I just lost more weight, I could find a man. The problem wasn't my body, it was that I was going for men with a narrow idea of what was attractive and couldn't stray from that.


So, the challenge here isn't what other people think about your situation, it's what you think of it and what you think people living a similar life bring to the table. You said it yourself: you dated younger men who made less than you and who allowed you to dictate the direction of the relationship. Without that money or status, you can't do that anymore. That's what bothers you. You can no longer use your lifestyle or career to impress men. Now you actually have to be interesting and kind and engaging. Yikes. Can you do that? Of course you can.


You need an identity makeover. The identity you had was based on being the HBIC. (Head Bitch In Charge.) You're not that anymore, and that's probably a good thing. You need to figure out what you bring to the table beyond a pay-check and cultivate whatever that is. The beauty is that you can do both. You can re-brand yourself AND date, because you don't owe anyone an explanation about your life. At the end of the day, you answer to you and no one else. Don't be so hard on yourself and you won't be so hard on others.


I'm not going to spew a bunch of woo-woo nonsense at you. You've been handed something most people never get: a second chance to get it right. Don't wait for three ghosts to appear on Christmas Eve. You know where you can improve, so do it. Once you become more at peace with where you're at in life - especially if you work on your empathy and compassion - dating won't feel so intimidating.

Good luck!

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