08/24/2007 10:00 am ET | Updated Nov 17, 2011

The Ex File or Love's Labor, Not Lost

"Do you want to go out with my ex-husband?"

The first time I asked this question I was seated next to my friend Cindy at a sushi bar; she responded by almost choking on her ginger. "You want to set me up with Chris?" she stammered, both confused and amused.

I could tell this would be a tough sell -- a breach of the rule in the female code that says you steer clear of your friends' exes -- but I was undaunted, and convincing enough in my hyperbolic praise of him that she agreed to meet both of us for breakfast. "That seems relatively un-threatening," she smiled, even as she was saying goodbye, perhaps a little more quickly than usual.

Since this first proposition, I've asked other friends by email. This way, with only a computer screen to witness their reaction, they feel safer recoiling. I suppose I can understand their concern. After all, I spent seven years with the man; we were the It Couple of the newspaper we both worked for. With my second and favorite husband, I'd co-purchased a house, had torrid sex and equally volcanic fights, adopted one dog and two cats, co-raised my daughter from my first marriage. We had some serious history.

But he's remained my friend, and he's had a tough go in recent years. Lots of losses -- including his dad, his best friend, and a beautiful woman friend with whom he envisioned himself growing old. And I'm a sucker for both a friend and a cause. Especially if the cause is love.

And there was Cindy: a documentary filmmaker and avid dog lover who matches my photojournalist ex in those interests. She's a little older than he is, but then so was I. I didn't tell Chris I was setting him up. Cindy showed up at the local diner wearing mascara. It was not love at first sight.

"He's lovely," she told me later. "But I didn't get a spark. Still, I'd love to go dog-walking with him sometime."

At our next breakfast, I asked him what he thought of my friend. "Why are you asking?" he said suspiciously, almost forcing a worry-line into his perfect Italian skin. "Are you trying to set me up?"

Yes, I shrugged with feigned nonchalance.


"I don't know -- because it's what I do. You know I've done it for all my friends -- why not spread the misery around to family?"

It's true. At 50-plus, and having become a student of the choreography of the love dance by writing a newspaper column about it, my brain becomes a humming calculator of romance when I meet someone new and single. After I rule the men out for me, I immediately size up both men and women alike for possible introductions. Clickety-click funny, clickety-click intelligent, clickety-click, prefers reading to Giants games. My success record speaks for itself: two marriages and countless set-ups among my friends -- none of which led to restraining orders as far as I know.

"Also," I hesitated, "I know you've had a hard time lately..."

His eyes darkened. "And you think dating will help?"

"Couldn't hurt!" I shrugged, knowing full well it could actually hurt something fierce. But his withdrawal from life this last year seemed an open invitation for me to draw him out by meddling. And so I did.

When Cindy was a no-go, I thought of Wendy, a statuesque blonde who had contributed an essay to an anthology I edited. When they met, he was dazzled and immediately interested; she waved him away with a "let's be friends; I'm closed for romantic repairs." They have gone to see ballets together. But that didn't cut it as far as I was concerned. I was after love or bust.

Then I thought of Gayle. Like Chris, she is tall, sharply funny, not a casual dater; they both deeply desire the comforts of a settled-down existence -- the likes of which drove my restless younger self away from both my marriages. She is just out of a long relationship that had not treated her kindly, and Chris, at this age (especially compared to when we were together) is kindness personified.

I also recalled that when he first met her years ago, he had asked me if all my friends were this beautiful.

"Yes," I had responded ruefully. "All my friends are younger and more beautiful than I am. This way, no matter where I go, I will be the last woman anyone looks at in the room -- thus ensuring a smooth slide into middle-aged self-esteem death."

I posed the question by email to Gayle; she responded with a slightly confused, "Are you sure?! If so, I'd be up for it..." I learned later that she called our mutual friend Julian to try to ascertain if this was weird or not, and wondered whether I was going through some kind of atonement process. Julian assured her I knew what I was doing.

"But why are you doing it? Really?" Julian demanded when we spoke of it.

Both have right to wonder. It's not like Chris was a picnic; 20 years ago when we first met, he was a brilliant, dark and angry young man. Not easy to love, or to get love from.

So why am I trying to find him love now? It's... complicated.

The easiest answer is that our divorce borders on ancient history: now 14 years in the past. So easily hurt in my 30s, the walls of my defense are now as thick as a castle's. Besides, nobody shamed the marriage. He was good to my daughter, who was no picnic herself. The divorce was, if anguished, friendly. Non-combative. He could have opted to stick it to me, financially -- having come into the marriage with far more than I did. But he didn't, and insisted we split everything 50-50.

The less obvious answer is that as you get older, your relationship parameters shift according to your priorities. When you're young, ego and pride dictate that you want your exes to pine for a good long time -- if not forever. When you're older, forgiveness is all-important. Who has time to hold grudges? Shouldn't we spend our golden years painting and traveling and taking yoga? Besides, it's ten times more fun to funnel that energy into chasing the divine spark on behalf of people you care about.

My efforts are also about karma: trying to rack up some cosmic Brownie points before my ticket is punched. Perhaps if I find love for Chris, it will boomerang to me.

And maybe, just maybe, if I find him love, I will feel better about jerking mine away from him.

Besides, he paid me back already -- years ago. At least superficially. He is not aware of this (well, I suppose now he is), but close proximity to him allowed me close proximity to his hunky photojournalist friends, at least one of whom tackled me as soon as the divorce ink was dry.

"Sure, I'll date your ex -- why not?" Gayle emailed me back. Filled with high hopes, I emailed Chris a photographic reminder of what my friend looked like.

"Wow," he responded, "Now all I have to do is to get her to lower her standards."

"Come now!!" I shot back. "Where's the confident man I used to fight with 15 years ago? You still got what it takes! Although... you might need my with selecting your wardrobe... or better yet, I could take you shopping!"

There was an uncomfortable silence of 20 minutes or so, before Chris responded:


I knew he wouldn't take it well.

I weighed my words carefully as I typed: "I just think you've gotten kind of conservative and could use a cool new shirt or jacket. Nothing that makes you look like you're trying to be young, but a little younger than blue oxford cloth..."

To my shock, he agreed. "Sure, let's go clothes shopping, I think Target and Sears are open late." Oh, how he's always loved to give me grief about my designer duds.

So the day before he and Gayle were set to meet at an art fair near his home, we met at Macy's, which was packed with Christmas shoppers too frantic about their last-minute gift responsibilities to notice two middle-aged friends cracking wise in the men's department.

I suggested a sweater with oddball knit patterns. "Too Tony Soprano," he frowned.

"I do need new socks!" he held up some hideous argyles and did a Vanna White display gesture.

"Clearly," I sighed, "these would seal the deal."

Finally, I convinced him to try on a Hobie bowling shirt, in shades of maroon and tan. A little young for him, granted, but still appropriate when you want to show you're a man of the 00s, with a little flair and a sense of humor.

He went for it.

I waited breathlessly for word of the date, which came four hours after it started. "She's fantastic," he emailed, "But I'm not at all sure she's interested." I told him I'd try to get her response, and reassured him that Gayle likes to play it cool.

When I asked Gayle bluntly what she thought (as all yentas must do), she responded cheerfully: "Chris is great. Super nice, funny, not hard to look at. And I'm supposed to tell you that he's a snappy dresser!"

They had date #2 later that week. But when I met her for coffee and asked if she thought there was a future there, she smiled, but shook her head no.

"I still think about my own ex too much, I think," she said apologetically. "I think it's just too soon. It felt weird to be kissing someone else."

Kissing? She and Chris were kissing? I felt a flush coming on, but shook it off as I thanked her for her candor. I guess the walls of my defenses aren't quite as castle-thick as I thought. Maybe more like pup-tent thick.

I asked her to do the right thing and let Chris know, and she said she would. I felt a little bad for them both; dating, break-ups, low self-esteem at middle-age -- it's all awful and more than enough reason to pack it in and embrace solitude as a lifestyle choice.

Then again, I'm wondering about that attractive woman author I just met at a party who wrote the novel about Mary Lincoln; didn't someone say she was single?