Let me take you back to my first real date a year after I was widowed following a thirty-two-year marriage. I was sitting on my living room sofa with Mark, an Alec Baldwin lookalike with a gym fixation. (I’ve always had a crush on Alec Baldwin). We’d just returned from a romantic dinner and walk through downtown San Francisco holding hands.

​Red wine in long-stemmed glasses? Check.

​Fireplace crackling? Yup.

​Lights dimmed invitingly? Got it.

​It was the mythical third date. Having only met for lunch before, this was our first nighttime outing. Even more exciting, he was going to be sleeping over on that very same sofa because he lived over two hours away. I wondered whether he’d be staying on the sofa all night.

He took a sip of his wine, put down his glass, looked deep into my eyes, and said, “I need you to know something. For a long time, I’ve been really unhappy.”

​”Oh?” I replied, thinking I might be the one to bring him joy.

​”Before anything happens, I need to tell you about the woman who ruined my life.”


​He then launched into the story of an ex-live-in girlfriend who he described as an amazingly hot blonde with breast implants (not that I needed to know about her breasts) who was exactly his physical type. I also learned she’d wrecked his finances, been mean to his kids, talked him into buying a house he couldn’t afford, then cheated on him with a guy from the gym.

​”After her, I sort of lost hope,” he concluded what seemed like many, many hours later. Needless to say, we did not kiss passionately (or at all), dazed by our good fortune at having found each other.

​Mark stayed on the sofa that night.

​The next day at brunch over Eggs Benedict, he monologued about several other women who’d allegedly failed him. It was a long time before I could order Eggs Benedict again.

​The date was not a success.

​Nor was our next date which, in my inexperience, I agreed to, thinking Mark might improve over time. He did not. Even though he’d told me in our pre-date conversation that he was done talking about his past and was ready “to focus on us.” It was false advertising, and I was treated to yet another evening of the women who’d done him wrong.

​I did not see him again. But that date turned out to be a microcosm for many that followed during my years of middle-aged singledom. From it, I learned several, oft-repeated lessons.


Despite having broken up years ago with The Woman Who’d Ruined His Life, Mark still hadn’t processed his pain, causing him to turn his dates into de facto therapists. He was Robert Hays in “Airplane,” recounting his epic love story to the unwilling passengers on the plane andrelegating his dates to bit parts as his listeners.

​There are times when we are so raw that denying our pain is virtually impossible. We are our pain. It consumes our very beings. If you’d talked to me soon after being widowed, my loss was all I could talk about. No, I was not okay. (Grief therapy helped).

​But that doesn’t work in the dating world. We need to make a conscious choice whether we’ve processed our past relationships enough to take on a new one. Otherwise, we’re draining our prospects by turning them into sounding boards they never agreed to be.

​As I continued to date, I’ve met far too many men who nattered on about their exes like I was an emotional labor machine. Did they really think we were going to bond over my bashing a woman I didn’t even know? Like I was going to chime in, “What a bitch, but I get being a sucker for a hot little body. Got any pictures of her?”


​Mark acted like fate had conspired against him, first one unfaithful blonde, then another, followed by a pretty brunette (the one that got away) who wasn’t ready for love, followed by another who…you get the picture. But really, if you keep having failed relationship after failed relationship, shouldn’t you take some responsibility for them?

​I remember wanting to tell Mark, “My husband died, you just kept making really poor choices.”

​When you tell someone about all the losers you’ve been with, they’re going to wonder why you kept picking those people. (Gee, another emotionally unavailable one, why am I not surprised?) Not to mention considering whether if the way you treated them contributed to the break up. Mark was probably driving his prospects away, as he did with me, by revisiting his exes in excruciating detail. And then you’ll just be the next woman who done him wrong.

​He could have had any number of futures, but he was so immersed in the past he precluded all of them. And he self-sabotaged those futures by not allowing himself to live in them.

​When I told him I didn’t want to see him again, he acted surprised, but really, he was still living with his exes. He’d never tried to be with me.


​I think it’s the way people of my generation (middle-aged folks) were brought up. Many of us women were raised to think about how we make other people feel. We’re taught to be pleasant and unobjectionable, not to take up too much space, or raise our voices, or be openly critical. (This did not serve me well as a litigator.)

​Many of the guys got a better curriculum: they were taught to make themselves heard.

​This fails all of us in dating land.

​It looks like a first date where the guy talks a lot about himself, but neglects to ask the woman anything about her life. He may, without encouragement, pontificate on how to select the proper tires, or diversify one’s investments, or reform the United States Senate.

When he asks for a second date, he’ll be met with a polite no and a vague excuse, like “I’m so busy for the next few weeks” or “We just didn’t gel.” He’ll be bewildered since things seemed to be going so well. He won’t understand his date crossed him off because, like so many others, he didn’t try to get to know her. Her remarks were just a springboard for more self-talk.

​After his monologue on the couch, Mark concluded with, “As a widow, I know you understand pain.” But he never considered whether I wanted more heaping tablespoons of it.


​After that first evening with Mark, I never should have taken him to brunch the next day wherein I was treated to more tales of woe. And I certainly shouldn’t have agreed to another date. I had no reason (except misplaced optimism) to believe he’d be any different.

​But not having dated in many years, I trusted him when he said he was ready to focus on us. When I told him during our second evening that I was sick of hearing about his exes, he just said, “Yeah, I’ve heard that before.”

​But he hadn’t seen it as a call to action.

​I would have re-written his profile to read: “Looking for a woman to share my pain. Degree in abnormal psychology a plus. Must enjoy long walks watching me cry, romantic dinners listening to me talk about other women, and sex where I cry out their names instead of yours.”


​Dating Mark started out as a rom-com where the plucky widow, ready to find love for a second time, meets what looks like a cute, possible Chapter Two. In reality, she winds up with a guy who’s an ambulatory cautionary tale about letting go of the past.

​But maybe it was what I needed: a reminder to be grateful for what I did have, including many years with my beloved husband. In contrast, Mark showed me that spending our dates obsessing over our woes was its own form of solipsism. Our prospects haven’t signed on to fix us.

His soliloquizing also showed that we need to be curious about the people sitting in front of us. Something wonderful happens when you give someone the conversational space they need to talk about their passions. They come alive, they start to glow, and they’re thrilled to be talking to you because they feel heard. But you need to give them room to do that.

Dating offers possibilities, like the many worlds theory where different, alternative universes narrow down to one through the actions of the observer (or something like that). But you have to be open to those possibilities and to engage with your dates. Mark was basically engaging with Mark.

My first date post-widowhood was not how I wanted to learn to live in the present, but it did teach me how much we hurt ourselves when we live in the past.

(Previously published on “P.S. I Love You” on Medium).

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