Dating After Fifty: Compromise and Tolerance

By Sherry Halperin

WJF 51 seeks intelligent, handsome, witty, creative, self-assured, financially secure WJM for fun, romance and…

If feels like just yesterday that I scoffed at that personals ad in the Los Angeles Times. But it wasn’t yesterday; it was 1994, a few months after my husband of 26 years died.

I was fifty years old. At the time, the thought of being with another man, a man I would have to undress in front of (nothing on my body is were it used to be), a man who might expect me to bend to his likes and dislikes, a man who I would have to learn to trust and share…well, it was all too daunting. I adored my husband and father of my two grown sons. I would be faithful to him until the day I died.

My husband died, not me.

But nine months later, a friend called to ask if it was alright to invite a male friend to join us for dinner. I suddenly felt an excitement and anticipation that seemed foreign to me. Questions began to spin in my head; was I really trying to look sexy for this dinner date? Was it even a date? And then the realization hit me. It was my husband that died and not me. Yes, I wanted to feel sexy, alive, and desired by a man.

The rules have changed.

When we’re thrown back into the dating scene at mid-life, there is a lot to be learned. The rules have changed since we dated in high school and college, as well as the reasons. Baby boomer women grew up with the belief that to be whole and fulfilled, we have to be married. So as an older single person, whether it be by divorce or death, we scramble to satisfy that myth.

My Personal Perfect Man List.

I scrambled…to a tune of more than forty men in a ten year period. At first, I was trying to replace my husband. Later, I was trying to solidify what I wanted in a man. I made up my Personal Perfect Man List.

1. Taller than five feet eight inches. I’m five feet four inches and like wearing heels.

2. No skinnies. I prefer a man who has some meat on him. I’m quite zaftig and a larger man makes me feel “smaller.” Okay, I know that’s a huge dose of denial but it works.

3. Enough money so I don’t have to feel guilty when he treats me to dinner and a movie. It would also be nice if he could pay his own way on a vacation. I do not want to support a freeloader, no matter how delicious he is.

4. Funny—I need a man I can laugh with.

5. Honest—about age, marital status, toupees, illnesses, children, jail sentences, sexual diseases, and sexual oddities. This does not have to be discussed on the first date.

6. If he needs Viagra—fine. Just don’t complain about the cost.

7. Loves, not likes, animals.

8. Likes being near the water—loves boats.

9. Has a commonality of beliefs and cultural background.

10. Has a good image of himself, is creative, loves his family, and has a life of his own.

I took out personal ads in newspapers and magazines. I had a profile on every online dating site I could find. I hired a professional matchmaker to the tune of five thousand dollars to fix me up on three perfect dates. Friends fixed me up. I kept changing my Personal Perfect Man List.

Revised Personal Perfect Man list.

1. Height is not that important to me anymore. I no longer wear heels.

2. What does it matter if a man is skinny or fat? Note to self: Consider a breast reduction. That will help with the zaftig thing.

Absurdity.

I couldn’t believe the absurdity of these dates. What were these men thinking? One showed up wearing a Moose Hat—yes, huge ears attached to a baseball cap. Another came wearing a jump suit, the kind mechanics wore in the 1970s. One man wanted me to go to a nudist camp with him and another turned out to be a relative. But, I didn’t give up. There were more frogs to kiss.

I did wind up falling in love.

Ah, the wonderful feeling of waking up next to a man you didn’t have to impress by wearing new clothes for every date and refusing deserts when you really wanted the chocolate soufflé. The knowledge that I could love again was powerful.

Where is that perfect man?

As we get older, so does our baggage. We all have it, no matter how much of a catch we think we are. He is afraid of commitment. He smokes. He hates to travel. He drinks too much. He has horrible taste in clothes. Where is that perfect man?

Compromise and Tolerance. Those are the magic words for dating after fifty.

Again, I altered my Personal Perfect Man List.

5. Honest—you know, if he wears a toupee or has a pacemaker, I can live with that.

9. Commonality of beliefs—still important. Although, a nice Italian or Presbyterian is looking better by the month.

And sex. Yes, it can be amazing in midlife. If you’ve gone through menopause, there are no worries of becoming pregnant. By fifty or sixty, we better have learned to laugh and enjoy intimacy because when it’s all added up, what can possibly be more important?

6. If he needs Viagra – I’ll chip in.

For ten years I was on a dating marathon. I gave the men names, like Turkey Neck, Jumpsuit Jim and Liar, Liar Pants On Fire. Some men I only saw once. That was enough. Some dates lasted under fifteen minutes…fourteen minutes too long.

Long term relationships.

I had long term relationships with two younger men…Stud Muffins, I called them. It was wonderful. They taught me you can be sensual and satisfying at any age and with any body. I was proposed to twice and refused both times. When it’s right, it’s right. Hopefully, we have learned that when it’s wrong, we say no.

Growing and learning.

Through all the wonderful and horrific dates, I was growing and learning. I was becoming independent and trusting of myself. I learned that having a man in my life is wonderful, but not necessary. Going to a movie or out to dinner alone can not only be possible, but enjoyable. I cruised alone and made fabulous friends. I joined organizations and thought seriously about what I wanted to do with the final act of my life.

And in the end, what I discovered was, simply put…me. I once again became the woman my husband fell in love with. I am now ready to date. <<

Sherry Halperin is the author of “Rescue Me, He’s Wearing A Moose Hat: And 40 Other Dates After 50″ (Personal Perfect Man List excerpt: Copyright © 2005 Sherry Halperin. Reprinted by permission of Seal Press).