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The Challenges of Dating as a Single Midlife Mom

The new memoir 'Escape Points' manages to be honest, raw and funny

In wrestling, competitors are required to earn an escape point each match — they have to prove they can extricate themselves from tough holds.

In her new book Escape Points, author and Northwestern University journalism professor Michele Weldon explores all the nuances and metaphors of that phrase. She flees an abusive relationship only to have her ex essentially abandon her three sons when he moved overseas, providing no financial support and rarely communicating. Through a cancer diagnosis, kids’ injuries (all three were wrestlers) and challenging workload, she maintains her humanity and humor.

The following excerpt is a shortened version of Weldon’s chapter on the challenges of dating as a single, midlife parent, titled simply: Alone.

Raising the boys alone without financial assistance or physical reprieve kept me occupied, if not impatient. Meeting Mr. Wonderful was not the highest priority. In the time since my divorce, most of my first dates were coincidentally the last dates because I couldn’t wait to get home and call a friend or one of my sisters to laugh.

“How often are your boys away for the whole weekend?” one date asked.

“Never.” I noticed a perceptible shift in his demeanor.

And it was addictive, the feeling of being loved. I liked being able to relinquish control, even if just in the restaurant ordering wine.

There was the Italian accountant with the creaseless pants who asked early on our first date if I had my marriage annulled. He was Catholic and wanted to remarry and didn’t see the point of going much further if I didn’t conform to canon law.

Sure, some men were polite, attractive and intelligent, but for years no sparks flew in my direction and no one was ever all that funny, interesting or a better option than a hot bath, rented movie or a stack of new magazines.

Steady Going vs. Going Steady

The boys didn’t need any more surprises from a parent. I was predictable; I didn’t bring home any threats to their homeland security. I also had hundreds of papers to grade, articles to file for magazines and newspapers, books to research and write. I had to give speeches and go to conferences and meetings. I had to make dinners. I had to make lunches. I had to make breakfasts. It was easier to go to bed early, wake up early and get on with my day.

“He was so boring,” I told Dana, my former college roommate, on the phone after a nice date with a nice man who was nice looking. “I think he went through his entire day minute by minute in chronological order.”

“Oh, honey,” Dana said. “They are all boring. You just forgot.”

There were men I met in airports, on airplanes or in shared cabs when I traveled for work. A man on a plane sitting in the row behind me and the boys — on our one and only trip to Disney World, because honest to God who in her right mind would go back — asked for my card and if I wanted to go out for a drink once back in Chicago.

Michele Weldon Author and Book Embed

Meeting someone was not difficult. Men talked to me in grocery stores. Not that I am all that flirty, but I answer them, even if I know the question about where are the sundried tomatoes is just a ruse. Still, meeting someone who was worth taking a risk on was nearly impossible. The idea of being close emotionally or physically with someone — anyone — was far too unsettling. I said no, thank you, to any offers but took the compliment they extended and that was all I needed for a while. I guess I could have taken a chance on one of them and fallen in love. But I dared not — the terrified of being fooled again thing.

Learning to Trust

Staying out of the game was also about more than not wanting to waste my spare time. It was about my ability to trust someone, anyone outside my immediate family. When you get trampled, really trampled as I did in my marriage, it is not high on your to‑do list to throw your heart into the center of U.S. Cellular Field or Yankee Stadium.

It was easier to be alone. It was cleaner, less dangerous, less fussy, and it definitely made me less insecure. No heartache. I spent so many years without romance, filling up my life with my children and my work and every detail to keep it all afloat, and my needs receded.

It was not even noticeable at first; I stopped wanting and figured that wasting my time mourning the loss of real affection was like ranting at a sunset or a rainstorm. When you let go of the need, the need lets go of you.

Besides, I have had my heart broken open. So my heart opens only a little bit at a time.

Then in the summer of 2004, I suspended my fears and disbelief and waded slowly into a relationship with a man who was completely unlike my former husband. I regularly patted myself on the back for slowly falling — it was more like tipping or leaning — in love with a man who was kind, sensible, methodical, calm and everything else my former husband was not. I loved him for who he was, but mostly for who he was not.

And it was addictive, the feeling of being loved. I liked being able to relinquish control, even if just in the restaurant ordering wine. We were together for almost six years. It was great, until it wasn’t. Nothing traumatic happened, it was just over; his choice.

Explaining Single Mothers

But here is the thing, and here is what so many men miss: Women who are charged with doing it all — women like me who care for children and sometimes elderly parents and homes and careers — sometimes we want to do one less thing.

Sometimes we do not want to be the only one to take out the garbage and drive to the store.

Sometimes we are so tired of being together and in charge, we do not even want to talk, listen or pick out a movie.

Sometimes we would rather have a hot stone massage from a total stranger than a conversation of substance.

The problem is, no matter how much we say we are here for you, we can’t be here for you only. We just can’t.

It’s not a lie that we love you deeply and we do wish we could be yours alone, but we can’t. There are other people we are in charge of, who have no one else. We can pretend well enough in our lace dress with the Spanx underneath on a Saturday night to be sexy and carefree at the Brazilian restaurant that doesn’t get moving until 11 or so, but it will be Sunday soon when we will have to go to Target to buy deodorant and peanut butter and poster boards.

We hope you understand, but the truth is, few do. Being in demand at work and home is not an aggressive act on my part. It is not at all about abandoning your needs. If it upsets you that much that I cannot sit in your den watching CSI every night, please go to the grocery store for ground sirloin, milk and hamburger buns, and I will have an extra hour to spend with you and give you my full attention. I will watch CSI, but just one episode.

I can never stop being a mother of three sons, because that is who I am.

I can put my cell phone on silent while we slow dance in the den, but I cannot turn it off. Not on the anniversary of our first date, and especially not on New Year’s Eve. Because New Year’s Eve could produce the apocalypse for teenage sons. I can take a long weekend, but I need to go home Sunday night because I have to throw in a load of laundry and drive someone to school from my own home the next morning.

I do not want someone who is waiting for my ambition to subside and my children to get away from me. It is not that I do not know how to relax, but that I never want to be great at relaxing. I have things to do.

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