I’m Feeling Inferior to My Successful Girlfriend and Don’t Know What to Do.

I’ve been seeing this lady for the last 2 months. She’s funny, intelligent, educated and has money. She runs her own coffee place with her brother. Her family has had businesses in the past so I assume she’s relatively wealthy. She’s attractive, not beautiful. I’ve always been drawn to brunettes (she’s blonde) but I find her confidence and drive attractive. And even though I’ve dated more attractive women in the past, my main focus is whether there is: mutual respect and admiration; shared values; common interests; chemistry and passion and the way she makes you feel.

Things are going well. She likes me and I like her. She’s a really great kisser with plenty of sex appeal. We get along well and the conversation flows nicely. We’re both around the same age. I’m 47 and she’s 44. She married at 27 and divorced 3 years later. She has no kids. I have no kids either. She said her ex-husband was very money hungry and a very jealous person.

She likes eating out at nice restaurants, art and interior designing. She has a nice place and drives a nice Mercedes. She offers to pay on most of our dates and has probably paid the majority of them.

As for myself, I have my own place, have a job that pays okay and I’m happy. I’ve never been super ambitious. I like to travel and have fun. I work to live as they say. I come from a working class background and have never been concerned about being rich. Don’t get me wrong, I don’t want to be poor either but I’m not obsessed by money.

My issue is that I feel inferior to her. She makes much more money than I do and her family is from a business background but mine are working class. I often feel she’d be more suited to a businessman.

Am I overthinking this? Does she sound like a good catch to you?

Should I tell her I feel inferior? (I don’t want to).

Ready for Lasting Love?
Ready for Lasting Love?

Because I’m asking you all these questions, does this mean I’m not sure and I should end it?

I want a woman to accept me for who I am. I don’t want anyone to change me. She hasn’t given me any indication that she wants me to change. A few weeks ago, she asked me about my aspirations regarding work and I told her I’m not really interested in climbing the corporate ladder. There was no positive reaction nor a negative one.

It’s been awhile since I’ve had a long-term relationship so maybe I’m coming up with excuses not to.

Thank you for any words of wisdom you care to share.

I appreciate your question, Matt, and I’m sure all the women here appreciate it as well.

You actually said so much in your question that there’s not all that much for me to answer.

For our regular readers, I would guess that Matt is a pretty fair approximation of what regular guys feel around successful women. Not overly intimidated. Not impossibly fearful.

What determines our success in life is how we rise to face it [fear].

Matt feels the normal insecurities that come from a society in which men are still expected to be wealthier and more ambitious, despite the fact that women are more educated on the whole.

Your issues, Matt, don’t stem from anything surrounding her.

They’re really all about you.


Essentially, I’m asking you to make a decision: are you happy with who you are?

If so, you’re not inferior to her.

She’s not with you for your money. She’s with you because you’re a good, happy, authentic guy who treats her well despite the fact that he’s not made of money. Period.

The only thing that can drive her away are your own insecurities.

Appreciate her for her intellect, drive and generosity, but don’t dwell on it.

Fear is a very powerful thing. We all have it. What determines our success in life is how we rise to face it. Are we courageous? Or do we let fear win and conquer us?

You have a tremendous opportunity here to be a working-class hero. Make her feel safe, heard and understood. Appreciate her for her intellect, drive and generosity, but don’t dwell on it.

You are a catch. You are good enough.

If you believe it, I can almost guarantee you, so will she.