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I lost my fiancee to cancer in 2016. I gave up all my savings and my income, and went into debt assisting with her bills and well-being until she passed. I moved in with my parents, and in the last twenty months, I’ve worked my debt down to a manageable number that allows me to live a little while still being frugal. I make five figures, so it’s been a challenge. After taking the time to heal and grow, I’ve started to date again. My goal is the privilege of marriage and starting a family. The caveat is that I’m almost thirty-nine and will live with my parents another year to clear my debt in full. I’ve met some great women, but despite my great personal and relationship qualities, they don’t have the patience to wait for me when there are other men available who can offer them more right now.

If I wait until I build enough disposable income to support a relationship without a need to be frugal, that puts marriage and a family potentially in my mid or even late forties, if you factor in the time it could take to meet a compatible woman and quality time as a couple before marriage. I’m not sure I would still want to start a family at that age, so I would be a liability to a woman that wants kids.

But if I date now to establish a relationship with an eye on marriage, and a family in my early forties, I anticipate a lack of opportunity and quality options because my partner would need to be patient and willing to contribute to many of our dating costs, or content with a limited lifestyle for a while. My experiences have taught me to value and prefer quality and simplicity over luxury and pageantry, and I’m excellent at showcasing my qualities, but other men have so much more to offer in terms of the stability and entertainment factor to woo women, which is evident when women leave me for them, despite my positive relationship qualities.

Am I doomed to dating purgatory?

Jack

Dear Jack,

I’m sorry for your loss and for the circumstances in which you find yourself. I also want to acknowledge the harsh truth of your analysis. You’re not wrong that many women will see your debt, your living arrangement and your age as three strikes against you. In a world where most prospects will give you only one strike, that could be crippling.

But instead of looking at this as if you’re doomed, I want to try to reframe this as a positive.

I haven’t walked a mile in your shoes, exactly, but I, too, was dismissed by someone I really liked when I was answering phones at JDate in my early 30’s. She was ready for marriage and kids and I was a few years away from being fiscally ready to settle down.

I didn’t blame her for her feelings. I did know, however, that my situation was temporary.

I may have been making $30K/year, was applying to grad school, and living with a roommate, but I was also hardworking, responsible, ambitious and not content with my lot in life. That sounds a lot like your situation.

And while you can understand why women would pass you up given the “entertainment factor,” that does not necessarily reflect the feelings of all women.

Should you happen to meet a client of mine — a woman who has financial security but has never been treated well by a good man — you may indeed discover that she values your consistency, your kindness, and your character while you see yourself to the other side of this trying time.

I’m not saying it’s going to be easy (to turn things around). I’m not saying the volume will be plentiful (money and stability does matter).

I am saying that if you acquit yourself with women the way you did in your email to me, I think you may be surprised and delighted with the woman you get.

I am saying that if you acquit yourself with women the way you did in your email to me, I think you may be surprised and delighted with the woman you get.

She’s the woman who loves you for who you are rather than what you possess, and I predict you will both be handsomely rewarded for your patience.

Good luck.