How You Can Date When You Make More Money Than Most Men

She’ll fall in love soon… if she reads this column.

I’m 50, have two kiddos 19 and 15, African American, twice divorced. I’ve followed your content since the beginning. Your Why He Disappeared program was instrumental in helping me heal after my divorce in 2016.  

I would like a long-term partner/companion and I’m open to cohabitation, but not remarriage, until my last child graduates college, for financial reasons. I feel like I have analysis paralysis. I’m going on 1-2 dates per month, but haven’t found someone I want a second date with. I’m online 30 minutes to 1 hour each day, my profile talks more about values and compatibility than chemistry, and I feel I’ve really crystallized what I want in a partner.

My top 6 values are a man who’s loving, dependable, generous, compassionate, financially stable, and has a good work/life balance, BUT:

1. I expected to be dating more often and with better results and I’m not. How many dates should I be trying to go on to meet my goals?  I’m dating online and I go to events I’m already interested in.

2. As a high earner, I struggle a bit with whether I should date someone who earns less when I’ve had awful experiences with that, but it also limits my options if I only date people who earn the same or more.

Since this is the bulk of your clientele, what advice do you normally give your clients about how to approach and consider finances in dating?

Thanks, Evan.

Felisa

Dear Felisa,

Before I answer your question, please allow me to compliment you on how far you’ve come. Although I edited your question, I want to acknowledge to our readers that you have taken responsibility for your ill-fated relationships, done extensive therapy, and are actively implementing what you’ve learned.

This makes your dilemma even more painful because, on paper, you’re doing everything right. You’re not hanging on to your exes. You’re not giving up on men. You’re dating online consistently and are focusing on values, not looks.

But since you’re not seeing the desired results, you have no choice but to ask: what, if anything, can you do differently to produce a different result?

I’ve got two looong answers to that question. Strap yourself in! This one is going to be thoughtful, powerful, and probably, controversial.