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Shopping the Personal Ads

Cheryl Howard
Arlington, Massachusetts
Volume 23, No. 2

I take a deep breath and push through the doors of the Harvard Coop. Across the store among the people browsing through the art prints, a man slowly turns around as if sensing I was there. When he spots me, his eyes and face light up with a smile. He moved swiftly to my side and I realize, This guy thinks he’s 5’6". If he’s 5’6", I’ve just grown to 5’8". I don’t want to be the one to tell him he has osteoporosis. Maybe accepting dates from men ten years older than I am isn’t such a good idea.



I had just entered the nether world of dating through the personal ads. At age 46, after five years of being divorced, I had decided I had to be more aggressive if I truly wanted the mixed blessing of a man in my life again. My career wasn’t any help. I taught at a high school that had only two eligible men – one still lived with his mother and the other was manic depressive. My friends were no help. The few single men they knew were bachelors who were bachelors for a variety of very good reasons. The only person I knew who knew scads of men was my brother – a parole officer. The personal ads in The Boston Globe seem to offer more possibility.

When I embarked on this quest, I enlisted the help of one of my most stable friends. I figured that Bonnie could keep me out of trouble. After all the pranks we had played as counselors at Girls’ Camp, I knew I could count on her to sneak behind potted palms or even confront a serial killer or two if need be. She okayed my first ad:

A possibility to expand friendship with a creative, intelligent, attractive DWF, 46, who enjoys bookstores, self-development, Masterpiece Theater, art. Seeks honest, basically happy professional with a sense of humor, n/s [non-smoking].

The ad included a coded voice-mail number. The worst part of the procedure was taping a two-minute recording for interested callers to respond to. Three gentlemen callers materialized over a period of two weeks: Len, David, and Clark. 

On the phone, Len turned out to be a very gregarious man who was looking for a distraction from his job and from providing care for his father, who had Alzheimer’s. He had been a middle school counselor years ago and was now working at a mental health clinic. His favorite pastimes included watching TV sitcoms and videos, calling radio talk shows, and going to comedy clubs. He didn’t like museums, didn’t read much, and had an adverse reaction to born-again Christians and women who preferred "gentlemen." From my vantage point, other than both working in public schools at one point, we had nothing in common. 

As the conversation wore on, my skepticism grew. I wondered if he had actually read or listened to my ad. If so, the content seemed to have eluded him. His love of conversation – mostly his own – kept us talking for an hour. He joked, "I guess you’d prefer it if I wore a tweed jacket with patches on the elbows and smoked a pipe." I said that except for the pipe, the idea had its merits. He finally paused to ask, "Well, do you want to meet?" I said that being rather new at personal ads, at this point I would just keep his number and maybe get back to him later. (If there is a graceful way of rejecting callers, I never did master it.)

David made me laugh. I never actually talked to him. He was a 60-year-old scientist living in Cambridge who was into jogging. His voice on the recording was upbeat, but he felt compelled to point out to me that since he was sixty, that meant he was fourteen years older than I. The age thing cooled whatever curiosity I had. From my own observations, most of the women I knew who were older when they got married or married for the second time wound up with men about fifteen years older. My own father married a woman of fifty-three when he was sixty-eight. He had confided to me that many other women he had dated were nice but old [his age]. I discovered I wasn’t ready to give up my own age bias even though I could laugh at my father for his. 

Clark seemed a good possibility. He was a bank lawyer, working for the FDIC. He had a grown son, traveled to New York and Europe whenever possible, and enjoyed museums and classical music. Although he was 57, he said he spent a lot of time outdoors biking along the Charles River. I squelched my dismay when he mentioned his height, 5’6", reprimanding myself for being stuck on a preference for tall men. We decided to meet at the Harvard Coop art print department, get lunch, and go walking. 

At 5’5", I didn’t tower over the man, but it was evident that his claim to be 5’6" was wishful thinking. His purported athleticism quit after we had walked half a mile. His focus was on a good lunch. He suggested a Thai restaurant, and we spent a leisurely hour eating and discussing memorable meals. He was moving into a new high-rise apartment in downtown Boston and had had menus from his favorite European restaurants framed to go over the custom bookcase he had ordered for his cookbooks. 

All this chat was fun, but there was no chemistry between us. I decided to keep this meeting on a purely egalitarian basis. He seemed shocked when I told him we would split the lunch bill. "I never intended that!" he protested, obviously a man trained in the "old school" of chivalry. I just smiled and said it was only fair. We strolled around Harvard Square to walk off lunch and wound up looking at the play listings at the American Repertory Theatre. He invited me to pick a play we could go to. I heard Coach Bonnie’s voice saying, "Go on – you need the practice." With some misgiving, I accepted but declined his offer to pick me up. I explained that it would be just as easy to meet him at the theater since I lived so near public transportation.

The night of the play, I wondered if I had been too wary in turning down his offer. It was raining heavily, but I was too vain to wear sensible boots instead of my good shoes. Our conversation quickly lost its initial buoyancy. I found myself groping for things to say. My best efforts at humor were met with quizzical smiles on his part. 

The play turned out to be very amusing, and Clark and I laughed in the same places. However, I still didn’t feel any chemistry between us. At some point in the evening, it dawned on me whom he reminded me of: the rather unnerving photo of the wall-eyed French writer Jean Paul Sartre that I had tacked up during the unit on existentialism at school. Ironically, as I grew more uncomfortable, Clark seemed to grow more enamored by an illusion that we were hitting it off so well. During intermission he enthused over the next production: the Orestia Trilogy – a six-hour presentation with a break for dinner. I smiled but avoided taking the bait. At this point, a Greek tragedy would only exacerbate the situation. 

After the play we went for ice cream, the rain having subsided to a drizzle and both of us well prepared with umbrellas. At a cozy table, he mentioned what a wonderful smile I had. I flashed the results of three thousand dollars’ worth of orthodontia at him again and wondered how I could get out of this gracefully. My pragmatism intervened, however, when he insisted on driving me home. It was late, it was wet, and his car was right there.

Clark had only been in Boston a short time and was basically unacquainted with its suburbs. My focus was divided between giving him directions and composing a farewell speech. One question of his seemed so out of context that it caught me off guard: "Well, what do you think about dating?" I was so nonplused all I could muster was "Excuse me?" He repeated: "What do you think about Haiti?" I’m sure he must have wondered why my response to his query about the current American involvement with that beleaguered island was delivered with a giggle.

When we neared a particularly crucial intersection, I told him to pull over. It was my intention to point out how he would negotiate this spot on his return journey. Before I could say anything, he put on the brake and turned to me with such enthusiasm that I thought he was planning an ardent embrace. My words were almost a shout: "No! Not here! I don’t live here! I’m just trying to show you how to get back." When we reached my house a few minutes later, I took a deep breath and told Clark that although I had had a very nice time and he seemed a very nice person, I didn’t think this was the right match. He was deflated and had little to say besides a perfunctory goodnight. I opened the car door and fled. 

I had some pangs of conscience as I got ready for bed. The rain outside was torrential again, and I imagined poor Clark driving around and around in a strange neighborhood, trying to find his way home after being rejected. I promised myself that even though honesty was the best policy, if I ever found myself in a similar situation, I would delay the speech until I could give it over the phone to avoid spoiling an evening. It took a good three months to muster the courage to try again.

                                    . . . to be continued

Besides being a DWF, Cheryl Howard lives in Arlington, MA, and teaches English and Humanities at Winchester High School.

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