Your Last Chance for Love

Dating in late middle age.

Posted Nov 10, 2019

I would define late middle age as ages 50 to 70. You aren’t elderly yet, but you are beginning to think about how you want to live the rest of your life: When and where you'll retire and how long you'll have to work to afford it. You might really be looking forward to that future if you are happily married, finished paying off your mortgage and your kids’ college education, and have saved a reasonable amount for retirement. But what if you never married, never had kids, recently divorced and suffered a big financial hit, or recently lost the spouse with whom you hoped to grow old together? You might not be looking forward to the rest of your life.

You may find yourself in your fifties or sixties playing the singles scene with perhaps uncertain finances and a few health issues. Even though you aren’t officially old yet, you might have high blood pressure, high cholesterol, and high blood sugar caused by extra pounds you just can’t seem to lose. Your sexual functioning isn’t what it used to be. You don’t want to grow old alone and unattended, so you are hoping to find a life partner before it’s too late. You might hope to find yourself a healthy Sugar Daddy or Mommy to love you in your old age, but the following challenges might confront you in your quest.

Sugar Daddies and Mommies

The Baby Boomer generation and younger haven’t saved enough for retirement. The high cost of real estate, health care, and education has taken priority over saving for retirement. Wages haven’t kept up. As a consequence, a lot of late middle age single individuals don’t have enough money for retirement. All single people are looking for sexual chemistry, an emotional connection, common interests, good health, and a reasonable level of professional success in a long-term partner. Late middle age singles who are struggling financially may especially feel that they require a sugar daddy or mommy who will provide the comfortable retirement they can’t provide for themselves.

Financial inequities between dating partners create an imbalance of power between a “have” and a “have not.” The “have” feels that: "I’ve worked hard for my money for many decades, so why should I have to share it with you if we marry? Maybe I want to hold out for someone as affluent as myself or maybe I want to make sure my kids get a nice inheritance." The “have” feels he or she has the power in the relationship and should be able to dictate its terms. The “have not” feels that: "If you really loved me and were committed to me, you would commit to taking care of me in my old age as I will commit to taking care of you. I’m not trying to steal your children’s inheritance or angle for a big divorce settlement if it doesn’t work out. I just don’t want to feel like I’m your temporary escort service."

Are You Healthy for Your Age?

Good looks are important at any age. Humans tend to be attracted to youthful beauty because it's a marker of fertility and physical fitness. In late middle age, we will be attracted to people who look good for their age. Do our dates look young or old for their ages? Do they take good care of themselves? Do they suffer obvious or not so obvious health problems? You’re looking for someone with whom to grow old healthfully. You’re not looking to be a nursemaid for someone who is not going to make it to a ripe old age. People who have spent a lifetime eating too much, drinking too much, smoking too much, or getting too much sun may now be starting to suffer the health consequences. And in late middle age, people start to more frequently suffer the bad luck of acquiring diseases like cancer or Parkinson’s that might not be a result of lifestyle choices but of genetic predisposition or random occurrence. Late middle age illnesses might not only shorten one’s lifespan but might already be adversely affecting one’s energy and sexual functioning.

A power imbalance arises when healthy late middle age singles date less-healthy peers. Naturally healthy middle-age singles will want to be with someone as healthy as they are. Naturally, not-so-healthy late middle age singles will also want to be with someone healthy because it is human nature to be attracted to someone who looks fit and youthful for their age. Not-so-healthy late middle age singles hope that their personalities, affluence, and potential to eventually overcome their health issues should work in their favor.

What to Do?

Sometimes people dating in late middle age act like they are back in high school. They are looking for the validation of winning someone out of their league who can give their egos a huge boost. But they are not in high school; they are late middle-aged adults who may have serious financial and health problems and may still be nursing a grudge about failed past relationships that bruised their egos. Of course, if, in the end, no one is good enough for you, you end up with no one.

Fulfilling marriage vows to remain committed in illness and in health seems far off when you marry in your twenties or thirties. It’s not so far off when you marry in late middle age. So, maybe to date successfully in late middle age we have to eat a little humble pie. We’re not going to sell ourselves short and settle for partners with serious financial and health problems that may be of their own making when we have worked hard all of our lives to take good care of ourselves. We don’t want to go down with a slowly sinking ship. But we might have to join forces with someone who is responsibly struggling to stay afloat economically and medically. Perhaps as a team we can fare better than either of us could on our own.


Josephs, L. (2018) The Dynamics of Infidelity: Applying Relationship Science to Psychotherapy Practice. Washington, D.C.: American Psychological Association.