When she snapped her fingers at the waiter for another drink, I thought, I’ve got to get out of here. I wished that she would just disappear in a puff of smoke, like the Wicked Witch in the Wizard of Oz.

In retrospect, there had been a number of red flags in our Match.com exchanges that I had completely ignored, like Stop signs on a deserted country road. I had been without a romantic relationship for months, so it was pedal-to-the-metal time. 

Her main profile picture was beguiling enough, showing auburn hair and a slightly self-conscious smile. It seemed to be a posed studio shot, which sometime later I found to be a declaration of, “This is as good as it gets” in terms of looks. It showed her in a blue cotton shirt with just a single button fastened and the collar folded open, exposing both a slight cleavage and a bit of bare belly. In Match terms, it was a very sexy photo, brimming with romantic possibilities.  

But it was also a bit washed out, like it had been produced on a cheap ink-jet printer. Her profile said that she worked in advertising on the creative side, which had been my ex-wife’s line of business, so I knew that the photo needed more saturation – and that she should have known as well. 

The next indicator of trouble was the target audience she declared. Her profile said she was “Seeking Men 38-59 within 100 miles of Westport CT.” That was casting a very wide net for a seemingly attractive 40-year old, both in terms of age and the distance she would consider for a relationship. It was much more common for women to specify an upper limit within five years or so of their own age in order to ward off the geezers, and also stay within ten to twenty miles of home to make it easier to conduct a normal relationship.

But Holly was willing to go up almost to age sixty – and drive a hundred miles? I should have seen that as a sign of desperation, which when combined with her apparent good looks translated to a high probability of non-trivial personality quirks. 

You may think this is reading way too much into a simple dating profile, but you would be wrong. Over the years I came to find that small clues like this are reliable tells in the world of online dating. I would scour profiles for subtle insights, like an HR staffer screening resumes for misspellings. I would rule out all but the most attractive women when I found more than a few red flags – unless I was a little desperate, which as it turns out was a fair bit of the time.

So, I wrongly interpreted her favorite pastime – horseback riding – as merely a bit exotic, instead of as a possible indicator of being an expensive date. The more Match dates I endured, I came to find that favorite activities like “fine dining,” “foreign travel” and “wine tasting” inevitably turned out to be giveaways of expensive habits, often acquired in a former life with an investment banker. They’d gotten used to the good life with a bad man and were plainly seeking the better half of that equation in the next round.

And then there are the outright lies, like Holly’s claimed drinking style: “Social drinker, maybe one or two.”  When she snapped her fingers at the waiter, it was for her third Cosmo, and she was just getting started. 

The other red flags only made bitter sense in retrospect. Her primary profile description or “handle” was “Striking Ivy Leaguer,” and she claimed to speak French. This combination suggested at least a bit of arrogance. And she professed to “non-conformist” politics. What does that mean – Socialist? Libertarian? Nudist?

And finally, her enigmatic parting profile line: “At the moment, I’m into being laconic and it’s quite difficult here... but perhaps this is enough.” It probably meant that she was being brief because she found it hard to describe herself to strangers. But it also could have been the last line of a suicide note.

 
Today, I would describe such a profile as being “covered in 10-foot pole marks” and pass it by with a shudder. But in the desperation of my early divorced experience she seemed a reasonable prospect, even though she disappeared for a month after I playfully suggested that she tune up her washed-out profile pic. (Gaff!) But she responded to my plaintive reconnect email with her phone number and a suggestion to call that very night. I quickly complied, and after a brief conversation, we agreed to meet at a local restaurant the next weekend.

I made reservations for eight pm and arrived early in the hopes of finding seats at the bar in case she wanted to have a drink first. That hope was dashed when I found the bar three people deep, all beckoning a single, methodical bartender who kept his eyes low to avoid encouraging more pleas than he could satisfy. I finally got a drink and moved over to a large picture window at the front of the bar, to watch hopefully for my new love interest. She was nowhere to be seen.

That was when I first encountered one of the oddest phenomenons of Match dating – meeting the person you’d rather have spent the evening with while waiting for your Match date to arrive. Why it doesn’t happen so easily when I just go to a bar alone, I will never know. Maybe it’s the vulnerable, hopeful look on my face, or maybe it’s just coincidence. But it’s happened to me a number of times, and it’s like the kiss of death for the impending date – I’m disappointed even before it begins.

As the clock approached 8:30 and I checked out the window for the twentieth time, a cute brunette, maybe thirty-five years old, touched my arm and asked me who I was looking for. Exasperated at having been stood up, I just blurted out, “a Match date.” She laughed and introduced herself as Gail. She said she’d heard such bad stories about it that she hadn’t tried it herself. Immediately she seemed immensely attractive, and better yet, present and available. And yet I was trapped by the impending arrival of my online mate, burgeoning flaws and all. 

Just as the conversation with my new friend started to warm up my cellphone rang. I answered, and of course it was Holly, who just said, “It’s me – I’m late.” By then it was 8:45 pm and I was well aware of her tardiness, so I asked where she was. She said northern Westport and described the circuitous route that she planned to take to get to me. I suggested a more direct route, which annoyed her enough to cut me short by saying, “I know how to get there.” She hung up. 

I was stricken her terse tone and began to wonder what I’d gotten myself into. I walked over to the maitre’d again and asked him to push my reservation back to 9:15, and as before he said he would do his best. It was prime time on Saturday night and our original table was long gone. 

Even worse, the call from my erstwhile date scared off Gail. I don’t think I was alone in hoping that the Match date would be a no-show, but during the call she refocused on a female friend, leaving me to my fate. At that point in my Match experience I thought it would have just been too crass to intercede and ask for her number. But today I would make that move without a second thought.

So, I was left to wait for Holly, gazing up the street towards the parking lot, hoping for the best while tamping down a growing sense of dread. My fears were realized in full ten minutes later when I spied a woman marching down the street in an obvious hurry. Her hair seemed redder than I remembered, which may have explained the washed-out profile photo, which had transformed it to auburn. 

But as she got closer, the look on her face was instinctively terrifying to me. Although she was an attractive woman, she had a scowl going that reminded me of an angry Miss Piggy, strutting along with her nose up in the air, spoiling for a fight. I know that’s not a kind characterization, but it was disturbingly accurate.

My first panicked thought was, “This place has a back door - maybe I should run.” But I just couldn’t abandon the meeting like that, leaving Holly stranded and wondering, even though she was an hour and twenty minutes late and in apparent distemper. Grudgingly I turned towards the front door, and Gail gave me a little thumbs-up. Oh God, I thought, a witness.

Holly burst through the curtains that kept the cold night air out of the bar and gazed around the room, looking right through me and focusing on the bar. I walked over and introduced myself, and she said, “Hi, nice to meet you. I need a drink – will you hold this for me?” She doffed her coat and shoved it into my arms as she headed to the bar. She extracted a twenty-dollar bill from her purse and waved it over the throng, urgently trying to get the bartender’s attention. 

Holly was so intent on getting a drink that she roamed up and down the bar, following the bartender like a linebacker shadowing the opposing quarterback. I made no attempt to start a conversation but used the surplus time to check her coat and thank the maitre’d once again for doing his best to find a table for us. As I waited, Gail gave me a puzzled look, and I could only shrug my shoulders. An awkward ten minutes later Holly returned with a half-chugged Cosmopolitan. 

Satisfied, at least in the moment, she half-apologized for her late arrival, giving no explanation. She must have been hungry as well, because after just a couple words, she spied the maitre’d, marched over to him and demanded to know when our table would be ready. I trailed behind her, waving my arms to get his attention and mouthing a silent, “It’s okay – it’s okay” at him.

When we finally got to talking, Holly was a blur. Still in a hurry from wherever she had been, she recounted a host of unrelated details of her day and life, in a seemingly random order, finally settling in on politics – a dangerous topic for any new acquaintanceship. 

After rambling on for five or ten minutes she took a position that was so inane that I’ve since driven it from my mind. But at the time I was striving to understand just what she was talking about. Like a good salesman I was asking open-ended questions and then drilling down for details. After a few fruitless rounds of this fact-gathering she declared in a huff, “I don’t want to talk about it anymore.”

This dodge gave me a sudden flashback to some of the more frustrating moments of my marriage, when my ex-wife abandoned a vexing conversation with that same age-old female dismissal: rather than finish the bad program, she abruptly changed the channel. I’d only just met Holly, and already we were communicating like a stale old couple. After ninety minutes of waiting and twenty more of incoherent monologue, I was quickly losing interest.

But then the maître’d appeared and said our table was ready. She gulped down what was left of her second Cosmo, ditched the glass on the window sill, and took the lead to our table. I followed meekly, glancing desperately at the back door while trying to avoid Gail’s gaze. And then we were seated, and she snapped her fingers at the first waiter to pass by to order another drink.

The restaurant was a Spanish tapas style, and after more drinks arrived we ordered a first round of food. Well into her third Cosmo, Holly started to get up a head of steam about another misguided political notion, which sounded like a story she had read in a comic book. No sign of the Ivy Leaguer anywhere, aside from an acute affection for alcohol. Finally, I’d had enough of both her and my Sam Adams Lager to make a move to alter the course of the evening. 

I started to morph from gentle, patient listening to a more aggressive, debating style. WHY did she feel that way about the President? I interjected. Did she actually read about it somewhere? (Mad Magazine, I wondered?) I began to dissect the flimsy justifications for the flighty opinions she was spouting, trying to find a credible source. She revealed none.

Finally, as we were finishing the tapas, she repeated her earlier “laconic” statement: “I don't want to talk about it anymore.” So, I took her literally.  I looked around and caught the waiter’s attention and gave him the little “check please” hand signal. And then I looked back at her and smiled faintly, in a relieved sense of satisfaction at finally having made a manly move after an hour of rolling with the punches.

 

Unsurprisingly, the conversation dwindled. 

Fortunately, the check appeared quickly, the waiter slyly dropping it directly between us. Holly glanced down at it and then looked up at me and said, “Do you want to split the bill?” She was obviously expecting me to gallantly grab it to offset the insult of my calling a premature end to the festivities. Instead I just said, “That would be great,” and was rewarded with a return of her angry look from the street. So, we went Dutch.

 

In the future I would learn to avoid buying dinner on a first date like the plague, remembering experiences like this one. But on this night, I actually got off relatively lightly, at least in monetary terms. 

We got up to leave, and it turned out that she was parked at the back of the building, outside the back door where I had almost fled. She had walked entirely around the building to come in the front door earlier. I went out with her, wondering exactly what to say, and hoping to keep her response as contained as possible. 

Amazingly, she turned to face me with a pleasant, expectant look on her face. I couldn’t imagine that she was looking for a kiss and could only wonder if she was waiting for me to suggest another date. I was flabbergasted, because that was the farthest thing from my mind at that point. 

What in the world do you say in this situation?  “It was nice to meet you?” “I had a good time tonight?” “You were worth waiting for?” None of the usual niceties was even remotely true. So, I just stuck out my hand to shake hers goodbye and said, “Good luck,” and then turned on my heel and dashed back into the bar hoping to find Gail. Alas, she was not to be found.  

Years later I would encounter Holly again at a live Match Stir Event, and mercifully she only remembered my face, and not the circumstances of our first and only date.