I lost my focus on the online dating pipeline one week when my long-time obsession, Susan, peeked at me on Match. Suddenly, no one else was interesting any more. A brief email exchange with her did not turn into the reunion date I’d been fantasizing about, so I found myself in the middle of a no-date weekend, hanging out alone at a local bar on a Saturday night while my son was with his mother. How could it possibly get worse? It did.

Earlier in the evening I’d had a “family dinner” with my son and ex-wife at her house. I was coaching his soccer team and suggested dinner casually to her when I picked him up for the Saturday morning game. He loved it when we got back together for a dinner but truthfully, I used it as a refuge sometimes when I was feeling lonely. I would drink wine and we wouldn’t talk about anything of substance. I’d keep everyone laughing, my son loved it, and I wouldn’t be alone – what you might call an emotional trifecta.

So, with a good dinner and a couple of wines under my belt I trotted off to the bar with some level of positive expectation, but not really. After all, it was Fairfield County, not New York City. I found an opening in the three-deep throng and ordered a drink, whereupon the lady just to my right decided to stand up and take a look around, in place. I made a little comment about her pirouette and we started chatting. 

She seemed familiar, but I couldn’t quite place her. She was bit plump, with a sagging physique. She was all false bravado about her job and life and kids, but it barely concealed her dismay at being over fifty, past her prime, and having to troll for action in a bar full of younger women. I knew how she felt.

 

So, she was happy to chat with me and tell me stories. Gradually it dawned on me that I had heard some of them before. I finally realized that she was one of my first Match dates, some two years earlier. A Seven Sisters grad after private school in France, fluent in French, naturellement, and terribly worldly.

 

She’d seemed fascinating when I’d had a long phone chat with her as I was driving to Maine to pick up my son from camp. She had told me about frequent athletic activities, including kayaking, and I started to imagine an athletic build to go with her engaging personality. 

That was one of my first encounters with what I call the “5 and 10 Syndrome,” where a woman's online photos were taken at least five years and ten pounds earlier. The round woman with sad eyes who showed up for that date just did not match my mental highlight reel.

I remember her saying in the parking lot at the end of the date, “Call me – I hope you’ll call me.”  It was almost a plea. I felt embarrassed – for her, and for not knowing myself whether I was going to call her. I suppose she felt my reluctance even before it crystallized in my own mind, because I recall debating later whether to try another date. But then the siren calls of other Match prospects kicked in and I completely forgot about her.

I’ve often wondered about the best protocol for breaking it off with an online prospect. Is it better to have someone wait around wondering for a week or two, until they realize I’m not going to reply? It’s awful when they come back and look at your profile again (and Match tattles on them). Perhaps they're wondering if you were really all that they thought at the time, or maybe hope you’ll note their interest.  I just don’t know if there’s a nice way to blow someone off, and with the numbers available on Match (and the frequent disappointing outcome) it’s a common issue.

So, my date ancienne and I continued talking. Pretty quickly I noticed her cute blonde friend who was sitting on the far barstool, sharing a substantial cleavage as she leaned in to hear the conversation. I tried to include her, but the music was too loud for her to hear. Finally, my past date introduced herself as Aimee and confirmed to me that she was the same person. I wondered for a while if she was just playing with me, or was just too embarrassed to say anything. Or maybe she was just drunk and unaware of the inevitable doom of the conversation. 

Finally, I had to broach the subject. “Are you a kayaker?” I asked.

She looked at me like I was a psychic, and said, “How did you know? Look out there in the parking lot. See that SUV with the two kayaks on the roof? That’s mine. How did you know?” 

Oh boy, I might as well be direct, I thought. “Well, do you remember our date,” I asked, “about two years ago?” 

Her friend heard this and started laughing, not making it any easier, and I had to smile myself. She racked her brain trying to remember me, while her friend and I chuckled nervously. She couldn’t place me. Could there have been that many? I wondered. Or am I that unmemorable?

 

I eased her struggle a bit by telling her I had a mustache at the time (which I was pretty sure was true) and she asked, “Where was the date?”

I told her, and her face took on the look of a having encountered a vile smell. She said, “Oh yeah. Do you remember what I said to you in the parking lot?”

OMFG. I realized instantly that it had been a poignant moment for her, possibly a moment of revelation, of vulnerability, perhaps of sincere pleading. She’d liked me and wanted to see me again, and instead I’d disappeared on her without a trace. 

“Yes, I do remember” I told her. 

 

“So, what happened?” she asked, twisting the knife.  

Somehow, despite the constricting feeling in my groin and puckering just aft, I received a divine inspiration. A golden little fib came to my mind, and I said, “I'm sorry, I fell in love with somebody else.” And it broke the spell.

"Oh, I understand” she said, looking away casually, “I did the same thing.” 

She did not elaborate on her counter-fib. I quickly changed the subject to the irony of the online dating scene, and we all survived the moment. She then told me that the blonde was her best friend Cheryl, and I realized my aspirations for her tonight were going exactly nowhere. Cheryl probably came to the same conclusion, and jumped up to talk to some other friends, leaving me and my once-dumped date to reminisce about a brief shared past that we’d both rather forget. Say, how ‘bout them Yankees?

A long twenty minutes later Aimee was building up a head of steam, telling me about family, life, aspirations - pretty much the same routine that I'd heard two years before. I felt badly, though, and tried to listen as best I could. But there was a band playing, and with all the other conversations around us, it was hard to hear. So, I had to incline my head down and towards her mouth to hear her talking.

 

This angle coincidentally put my stare directly on Cheryl about ten feet away, talking with a group of friends. Her tight little ass was wonderfully outlined in a clingy summer dress. I stared wistfully at it as Aimee droned on. I saw from her swaying body that she’d gotten a bit tipsy. And then she started feeling her own right butt cheek, smoothing her hand across her ass and squeezing slightly, cupping it like a man might do. It seemed like she was taunting me, but I would guess it was for no other reason than the pure, drunken, tactile joy of her own caress. But it was just too much to bear and I had to escape. I popped my head up and asked for the check.

I’d managed to buy only my own drinks in this little encounter, so the bill was small, and I paid with cash, as quickly as possible. Aimee of the Seven Sisters had become remarkably poised and parroted my move, simultaneously retrieving Cheryl from the crowd. So, we ended up walking out together, with the ladies leading, as if we’d just decided to have a threesome. I caught a look from one of the other guys in the bar as we trooped out, and he was smiling lasciviously. I gave him an "if you only knew" look that was ambiguous enough not to blow the story and followed them out the door.

But then as we walked down the sidewalk, drunken Cheryl noticed me as if for the first time. She slipped her arm around my waist and said, “Oh, are you coming home with us?”

I imagined the spluttering, volcanic reaction from Aimee if I were to accept this entreaty, so I was definitely not coming home with them. But it took every bit of willpower I could summon as a frustrated, drunk, horny guy to peel her arm away and say “No, I’m afraid not.”

Cheryl then asked, “Do I know you?” And as I turned in the other direction for my car, I said “Yes, I was on the other side of Aimee tonight, talking to you.”

And I fled into the night, not looking back.