Meet your match

It's a Wednesday night at the height of summer, a beautiful time of year to embark on a new venture, or so I like to tell myself. As I fuss and fumble with the curling iron, my carefully applied makeup is sweating off with the effort to style my hair just right—feminine but not too sexy. I've chosen to wear a green floral halter dress, bought for another occasion but not yet worn. It seems ideal for my first ever matchmaker date. I put on my flats to finish the look. I've never seen the man who's arriving at my door in mere minutes, so I can't be sure if he's taller than me.

I've spoken to the gentleman on the phone just once. He seems respectful, engaging, interested. Yet a few of his more pointed questions make me nervous. It's his prerogative; he's paid a good deal of money to a matchmaking service that helps successful, well off men meet the women they're too busy to find themselves. He has a vested interest in making sure I'm the right kind for him. Yet three of his questions have stuck in my mind: How is my relationship with my father? Why did my last relationship break up? And, my favourite by far, why have I never married? How could he possibly know that my fear of dating is grounded in not having the right answers to these questions?

So why exactly am I, at 48, travelling down this awkward road in an attempt to find the man of my dreams?

In my twenties and thirties, I just fell into relationships; I'd start hanging out with someone a little, and then a lot. I didn't have difficulty meeting men, so I left it all up to chance. But I wasn't counting on the slim pickings in midlife. And lately, after a four-year period of intermittent soul-searching about my commitment phobia, and not much dating, I've been hankering to try again. I figure at this age, a good 10 or 20 years with someone is manageable. I'm tired of cooking for one, sleeping solo, and I worry about being alone in later years.

Meeting the matchmaker

While browsing through a local magazine one night I happened upon a matchmaker ad featuring a well-heeled businessman in his mid-forties looking for a woman around his age. I had no idea what the competition would be like, but if I passed the matchmaker's scrutiny I'd get a date with this guy. The ad did not provide a photo of him, but I guess because he pays all the fees it matters only what the women look like. Feeling reckless, I tossed off an email to the agency, and although it didn't ask for one, I confidently attached a photo.

A few days later, I received a reply asking me to come for an interview. I cancelled once, then rebooked.

So, one sunny afternoon in late May, I dressed myself in youthful pink and went to see the matchmaker. The expensive office decor—rich leather couches, deep cherrywood desks—must indeed have been funded by affluent men. The meeting was brief, a mere 15 minutes. The matchmaker asked me the usual questions about interests, hobbies, career, family. Then she lobbed some curveballs: Would I date a visible minority? Of course. Would I go out with someone overweight? Well, yes, as long as he was healthy. Older? Sure. Younger? No, not again. How about someone with a disability? Hmm. I want to travel and to be active, so I'd probably have to say no. Does that make me sound unco-operative? Immature? Prejudiced? She took my picture, assured me that a number of her clients would like me and promised to be in touch. That was it. Painless.

Except, how silly it seemed to be extolling my own virtues to a stranger in hopes that she'd glean something that would click with the ideal man on her roster, about whom she told me nothing. As I walked out the agency door and into the sunshine, I tried to shake a nagging, how-is-this-my-life dejection.

I didn't hear a peep until mid-July. What happened to all those men dying to meet me? As I politely deflected questions from pals, I wondered what it meant to be rejected by a matchmaker and vowed to never try to go on another date. Ever.

Then my match called. I let it go to voice mail; I wanted to hear what he had to say before I responded. He had a pleasant voice, very proper. He said our matchmaker advised him I am "the one" for him. And this would be based on...what? Hair colour, charm, education, career? With some trepidation, but still willing to see it through if only for the sake of my curious friends, I returned his call.

Our phone conversation, which felt more like an interview, apparently passed his test. He seemed to like what he heard: pat answers to difficult questions.

Fine. I figured there might be time later for certain truths.

Rediscovering the meaning of "we"

The truth about my relationship with my father? About a year before he died, I went home to Toronto for a week to help my dad move. We'd been estranged for most of my adult life, but recently he'd been calling me regularly and taking an interest in me and my new West Coast life. Still, we barely knew each other. He was giving up his independence at this point; he needed chronic care, and his expression wore the frustration and sadness of this reality. Trying to draw him out, I asked questions about items we were packing up, and about his earlier life. He once had a job laying tile—I knew that—but when he said he was known for his mosaics I finally understood that he possessed a creative soul. This might well be why he had such a hard time being a steady breadwinning family man, the source of many marital fights that were the soundtrack to my childhood.

With weakened defences, and needing help to prepare for his new, diminished life, my dad let me cook for him, drive him to his doctor's appointments, to the store, the barber. I had never experienced such trust from him.

I learned, for me, the most affecting word in the English language is "we"—as in, What should we have for dinner? To hear the first man in my life include me was, to say the least, a relief. I found myself prompting him for responses that required him to use the word.

All of this happened smack dab in the middle of my last relationship—the one Mr. Match asked about. Since my ex and I were living together, I had my coveted "we," but no real commitment to go with it. I mistook the comfort of physical presence for something that, prior to that week with my father, I didn't know I was missing: love.

After we split, I discovered the midlife heart takes longer to bounce back; sometimes it tricks me into believing that I'm better off alone.

Regarding the dreaded why-have-you-never-married question, my easy answer is: "I guess I was never ready." But that doesn't cover it. My mother used to say I wasn't the marrying kind—by which I think she meant too serious, emotional and difficult to hold. "It's going to take someone very special," she'd say. I took that to mean I didn't have what it takes to "land" a man. "Not the marrying kind" became a self-fulfilling prophecy (one that likely had more to do with her unhappy marriage than my disposition) that wrapped itself around me in a thick, impenetrable shield to ward off any takers.

Of course, I reveal none of these details to my date. Besides, he says he knows enough about me to meet for dinner; he'll make the reservations and pick me up on Wednesday night. After waiting so long to hear from him, I now feel as if things are going lightning fast.

Too much, too quickly

When we meet at my front door I see an attractive, well-dressed man, the same height as me (so good call on the flats). He greets me with a (little too) warm hug, and once in the car he is already holding my hand. I extract it and tuck it underneath my jacket and purse. Another red flag: There are great restaurants in my downtown neighbourhood, yet he is whisking me onto the highway heading out of the city.

When I was a kid, just after my parents separated, my dad used to arrive unexpectedly to take my sister and me for a drive. I never knew where we were going, or when we'd be back. I'd grown up a little afraid of my dad's gruff voice and quick temper, so naturally I was a little anxious on these drives. Although I later realized this was just his way of spending guaranteed time with us, at the time I felt held captive. That's how I feel in this guy's car: kidnapped. I silently berate myself for not setting up an escape plan with one of my friends.

We arrive at a banquet-style restaurant, ostentatiously decorated with fake bouquets and an arched entranceway to the large dining room—probably meant more for weddings than first dates. My date, hard-working entrepreneur that he is, doesn't drink. So, despite desperately wanting a glass of wine to calm my nerves, I order a sparkling water. He begins to tell me about his life, his two kids and his two ex-wives. I listen as intently as I can while inhaling prime rib, but his story includes minute details of very personal conversations. It's too much information, and also sounds like a practised litany—something he's told in the exact same order and detail many times over. I can't say I'm getting any real sense of who this man is, other than by the sounds of it he's been terribly underappreciated by the women in his life.

In fact, all of it is too much: the massive, brightly lit, scarcely peopled, garish restaurant; the touching; the questions; his litany; and too much butter rub on my steak. I simply can't wait to get home. My date, whose tests I have apparently aced, ends our dinner by showing me photos of his kids and inviting me to Bermuda to spend some quality time together. I thank him but decline. The next day, I open my email to a letter full of compliments and future plans. "I'm just beginning to realize the potential of us." He asks me to reconsider a trip with him.

This is all too familiar. A few years ago, I met a drop-dead gorgeous, wealthy, artistic and intelligent man who invited me to his southern U.S. retreat. I kept refusing until my best friend asked, "What if this is your big chance?" He paid for everything: the flights, our extravagant meals, the pricey bottles of wine. He said he had no expectations and that it wasn't just sex he was after. He told me he was looking for a wife, that he had grown tired of travelling alone and wanted a companion, but halfway through the weekend I sensed he'd decided I wouldn't be the one. Probably he was just looking for sex and paid for it handsomely. This is why it's a no-brainer to say no to this man, his Bermuda offer and our alleged "potential." I've always done the infatuation and sex part of a relationship well; it's the inspection for marriageability that rattles me. I don't want to submit myself to either this time around.

A few weeks after our date, the agency emailed to say the gentleman had found a successful match, and his file was closed. I'm not sure if he rejected me or I rejected him. Maybe I adopted an attitude of self-sabotage from the start, but all I could see was his loneliness and his attempts to ease it by buying my attention and affection, all the while protesting that the women in his life never see past his money. The experience left me feeling lonely for both of us and hoping he really did find his match.

I hope I find mine too, although I think I'll take back the matchmaking reins.

More tales from matchmakers: Avra Goldenblatt gives up on cougar speed dating and tries a matchmaker. Feeling lost? Try our midlife dating guide!

This article originally appeared in the November 2009 issue of More