I’d started emailing Madelaine about two weeks before, at about the same time I was first talking to Patsy. Her Match profile bragged of boundless energy and challenged a man to keep up with her. She sent me a note titled “new at this and don’t know how you popped up...” commenting on a shot of me with my 12-year old boy: “Cute son.” And adding, “You 'never' drink? AA?”

 
I replied that I’d been sober for about a year, and she wrote back “let’s meet for coffee” and gave me her cell number. I reciprocated, but soon after she texted that she was heading out to the Hamptons for the Labor Day weekend, on what seemed to be a last-minute invitation. 

She left me a voicemail as she drove eastward on Long Island, complaining about the traffic, and suggested we chat while she drove. I wasn't longing for an initial conversation while she was heading in the opposite direction, so I texted her, “Hey - got your msg, talk next week... Enjoy.”

But before long, she replied: “Here in my college friend's $10M house on water in Quogue...doesn't get better than this! What r u doing this weekend? How many years do u have? I had 17...”

 
Now, in the world of Alcoholics Anonymous, using the past tense in terms of the years of sobriety you’d accumulated is not often a good sign. So I texted back my plans to go to the U.S. Open, and asked, “You back out there?” (AA-speak for drinking again.)

She replied, “I’m in + out. I’m not cuckoo but have 17 years.” 

Well, from an AA perspective, “in and out” actually is cuckoo, and is not considered sober at all. Considering I was in the first year of my own recovery, Madelaine was not the ideal candidate for a romantic liaison. But she was cute and beguiling, and I’ve always been something of a risk-taker. So, we made plans to talk when she got back from the Hamptons.

 
She called me that Monday afternoon as she drove back, again in a massive traffic jam. She told me she’d been sober for seventeen years but had started "controlled drinking" again about a year or so earlier, and that so far it was going well. She mentioned that she had also been bulimic in her twenties but claimed to be fine now. This last factoid was a little too resonant of my alcoholic younger sister, who “learned” to be bulimic in her teens by regularly inducing herself to vomit after drinking too much. 

Madelaine was also a little potty-mouthed, saying “fuck this,” or “fuck that,” fairly regularly. For some reason I like some coarseness in a woman, because it’s authentic. I’ve discovered that ladies are not so different from guys in conversation or behavior, they just hide the rough side better than we do.

 

But not Madelaine – she was right out there. She asked me if I liked Robin Williams, which was a rhetorical question, because who doesn’t? Then she said, “I slept with him when he was in the area filming The World According to Garp.” She added, “He was a very creative lover.” Great news, I thought, she gets around.

She told me that she worked as a Public Relations agent, and had been a marketing executive for a local business. She was living in Westchester in the house she grew up in after tending to her elderly father for a few years until he went into a nursing home. She was also supporting two sons in college. So, I figured she had some level of stability to her. We agreed to meet the following weekend.

 

When I got to the restaurant that Saturday night, I saw her at the bar watching the Open tennis. She either didn't notice me walk in or pretended not to, so I came up behind her and whispered in her ear, "Who's winning?"

 

Without turning, she said, “Kim Clijsters,” and babbled something incoherent, making it apparent that she’d already had a couple of drinks. We bantered over he shoulder for a bit before she finally turned around and introduced herself, asking, “How did you know it was me?”

Notwithstanding the fact that she actually looked like her pictures (which is not always the case with online dates) I glanced down at her halter top and generous cleavage and said, “Well, I looked up and down the bar, and I was hoping it was you.”

“Good line,” she said, “I've already got a drink. I got here a little early.” 

She called the bartender by name to get me a drink. Lo and behold, it was Turner, the same barkeep who had plied my date Sicilia with red wine three years earlier prior to my escapade with her.

Turner had already given Madelaine a free wine, which called her out as a “regular” in the place. She ordered a cranberry and soda for me – without asking – and gave him $10 for both, suggesting we go to our table in the restaurant. I could tell she was a little buzzed, because she wasn’t the same talkative, boisterous woman she’d been on the phone. 

We ordered right away, and I went into my first-date monologue to keep things going, talking about how I’d raised my son from age twelve, doing the Mr. Mom thing while co-running a technology consulting company, and dishing about the “other Moms.”

The food came, and she quickly helped herself to the clams atop my linguini, still not saying too much. I went on with my routine. She wolfed her burger and fries, occasionally ending up with a fry sticking out of her mouth because she had shoveled too many in. It was a classic shit-faced act – a little numb, not too conversational, and light on manners.

 
As she carved her burger awkwardly and munched on fries, washing them down with red wine, the conversation lagged, and I decided to try an open-ended question that women usually spring on me.

 

"So what are you looking for in a man?"

She fixed her gaze on me and said, "Someone who will lick my nipples."

 

Then she paused, looking for a reaction. She got raised eyebrows and a mirthful look, so she doubled down and added, “Then lick my pussy - what else?"

It was too far over the top for a joke, and as drunk as she was, I had to think that it was shamelessly true, if just a tad premature. I looked at her to discern the real message from her face, and found an odd mixture of bravado and coldness, with a slight hint of a smile – a quietly pleased drunk.

I laughed and said, “Well, this date just got interesting.” 

 

But then she stared at me a bit too long with no change in that expression, not giving away either the joke or the authenticity of her comment. I wondered if I’d just failed a promiscuity test. 

Before long, she got up to go the Lady’s room. Because she was pretty drunk at that point, I wondered whether it was to pee or throw up. She seemed to sense what I was thinking, because before she left, she grasped my arm and said, “Don’t leave, please don't leave,” and then wobbled off. It was such a sad request, a moment of drunken clarity that she’d had too much to drink and needed to make a small amends, or at least ask for patience.

I hadn’t been planning to bolt but it did remind me of a text message I’d felt in my pocket a little earlier, so while she was in the powder room I checked. It was from Patsy, asking if I was interested in a sleepover. I thought, I just love options. I wonder where I'll be at midnight?

When Madelaine returned, she’d composed herself a bit, not looking quite as sloppy as she had just earlier. While she was gone I’d finished my dinner. She ignored the remains of her fries, and we chatted agreeably for a while. Then she crossed her legs under the table, and I felt her shoe drop off and hit my foot.

I said, “You lost your shoe,” and started to look under the table. 

She replied, “That’s okay, I got it,” and started feeling around with her foot. When she found my foot, she asked where the other one was, and I pointed down through the table and said, “About here,” wondering why she would ask. And then I felt her bare foot rising between my legs, working its way up my thighs. 

I've gotten crotch massages before from women, but never just an hour into a first date. The wry look on my face must have dissuaded her because after a brief exploration, she resumed the search for her shoe. I thought, Drunk Cinderella searching for her slipper. Then, No, even better – Cinderella the Slipper - Slipper-ella! It was an AA joke, on the premise of her slip back into drinking. I didn’t share it with her.

Then she switched gears. “There’s somebody I’d like you to meet. He’s in a bar down the street.” I’d already paid the tab, which the waitress had left when Madelaine was in the loo. We got up and started out of the restaurant, but she was a little unsteady and grabbed my arm. I asked her if she was okay and she said, “Yeah, just a bit tired,” which I recognized as a classic alcoholic excuse for wobbly behavior. 

   
We plowed on to the next bar, where we met a short, tanned, ultra-confident-looking man who Madelaine said was an old friend. He turned out to be Al Pirro, the former Nassau County First Selectman, and also the recently divorced ex-husband of Judge Jeanine Piro, the minor Fox News celebrity. He was with his girlfriend, whom he introduced as GloryAnn. 

I quietly asked Madelaine if it was actually “Gloria Ann,” but she whispered back, “No, it’s GloryAnn.” Apparently, GloryAnn had been seeing Al for quite some time. I wondered who in the world would give a woman such a name.

Madelaine dished with Al for a while, apparently knowing him well enough to gossip. Listening, I just kept the wry look on my face, because that was the kind of night it was turning out to be.

 

After exhausting the latest news, Madelaine said she needed to sit down and get another drink. She took a look around the bar, and seeing no open seats, said, “Let’s go, I’ve got another place in mind.” We said goodbye to Al and GloryAnn and trooped out the door, with Madelaine walking on her own this time.

But about fifty yards down the street, she stumbled hard, almost going down on the pavement. As she flailed to catch her balance, her entire left boob popped out of her halter dress. I caught her arm once again, and when she’d righted herself she addressed the maladjustment, deftly tucking it back in place.

 

I thanked her for the flash, and she smiled thinly and muttered, “You got lucky.”

 

I replied, "You're lucky that I was there to catch you!"

 

 She said,“Touche´,” and we continued down the street in lockstep.

At the next stop, we found two seats at the bar. She tried to hook her purse under the bar but dropped it between my legs instead. She abruptly bent to retrieve it, turning her head sideways to reach, which left her face perhaps ten inches from my crotch.

 

She deadpanned, “Don’t get excited," and righted herself back in her chair, managing to find the hook for her purse this time. 

She’d made a series of comments like that all night. They might have been fun if she was still a twenty-three year old, or I was still drinking -- or both. But not really knowing her as an adult, the habit was just a little unnerving. 

I said, “You know, you’ve got a curious habit of saying provocative things without giving away whether you’re joking or not.”

She said, “Yeah, I do that a lot.”

At this point I was wondering, if I'd said just the right things earlier, or reacted more stereotypically male, or actually was still drinking, whether we would be back at her place right now, fucking vigorously – after the obligatory licks, of course. Instead, I was buying yet another round for a lady who hadn’t really needed the last three. 

This was the fundamental predicament of dating for me now: I just wasn’t into sloppy, drunk sex any more – that’s a tango that takes two to enjoy. When you’re not drunk, you tend to notice way too many incongruous details about the situation that diminish the overall experience, often to the point of failure – much like the evening’s date had been for me thus far.

Besides, I felt badly for her, like you do for any problem drinker who’s gotten themselves pickled in a tense or important situation and can’t get un-drunk to save it – if that’s even what they ultimately want to do. Most just keep drinking, and figure that sooner or later, it will become a valid excuse for whatever behavior occurs.

Finally, the conversation dwindled, and I decided not to try to keep it alive. She looked dully at her half-finished merlot and then up at me, and I said, “Let’s go,” nodding to the door with a half-wink. She didn’t protest, but teetered a bit getting back up. I grabbed her arm and this time didn't let go.

She directed me to the parking lot where her car was, in the direction of a homely Buick SUV. I said, “It can’t be the Buick.” 

She ransacked her purse and managed to find her keys. She clicked the fob, whereupon a Mercedes C300 right behind the Buick lit up. I led her toward the driver’s side door, doubting that I should let her drive, and wondering what the alternative might be, since she lived in the opposite direction from me and would almost certainly assume that I was going to invite myself in if I did.

 

But she immediately turned on her best imitation of sobriety, worthy of a State Trooper’s inspection. She started to get in the car, and then remembered me. She turned back, presenting her lips with half-closed eyes, waiting to be kissed.

I kissed her goodnight, a couple soft, lingering kisses with just one hand on her arm. She made no movement to or away from me to give me a clue as to what my next move should be, so I let her go, figuring if she was really interested, I'd probably get another shot. (Plus, Patsy awaited.)

I said, “Are you sure you want to drive?” giving her an opening to ask for my help – and company.

 

“No, I’m fine, really, thanks for asking,” she said as evenly as she could, and climbed into the driver’s seat without too much trouble. She buzzed down the window and said, “I had a good time tonight. Call me?”

 
I said, “Okay” without much enthusiasm, wondering if I was lying or not. 

 

She was clear enough to catch my flat response. Considering all the sexual cues from the past two hours against the reality of a ten pm kiss-off and no invitation to drive her home, I was thinking that there really should have been a much more sexual continuation of the evening.

She said, “Don't be bitter...”

 

I laughed and said, “Don't worry, I'm not.” It was a half-truth – no, a three-quarters truth. I was fairly well grounded in not drinking by that point, but there was still a part of me thinking, Shit, two years ago, I’d be banging you by now.

“Please call me, I'd like to see you again.” 

“Talk soon,” I replied.

 

She drove off cautiously enough, and I thought-prayed her luck and safety on the twenty-minute drive home. Just don’t take the Sawmill, I thought, it’s way too dark and windy.

After she was safely off, I called Patsy to confirm that I was on my way. I dashed over to my own car, which was in the same lot, and tried to think of the fastest way to Easton, CT. It was the Hutch and I found my way onto it in very short order... (to be continued in another story.)