Drinking and Dating: Dangerous Yet Fun!

I met Dean for drinks at a bar on the West Side. This was the culmination of the sudden blast from the past – getting an email from Tim (who then promptly disappeared) and then one from the man I was about to meet: Dean. He had contacted me last spring via the personals, only to bail on our date the day of, due to (he claimed) having met someone. Whether he’d met someone or just changed his mind it was clear he was not entirely truthful, since after he cancelled on me he was still online all the time. But alas.

So we arranged to meet at 5:00 pm, which I thought was a neutral non-date kind of time, and would allow me to be out of there by 7:30, 8:00 at the latest.

When I arrived, the bar was empty (one of the benefits of meeting someone at 5:00 pm on a Sunday evening), so when a tall man in jeans and sneakers stood up, I had no problem identifying him as my date.

“Hi,” we shook hands. “I’m Lily.”

“I’m Dean. Do you want to sit outside? They have a back yard…”

I trailed Dean the length of the bar and into the back yard. There we settled ourselves at a table and ordered: a Flirtini (me) and a glass of Pinot Grigio (him).

I studied his profile: he was really cute! He had a thin, angular face with high cheekbones and blue eyes. Unfortunately, he was wearing high-waisted jeans and sneakers, a look I abhor. If only he had worn low rise jeans and a t that wasn't tucked in! Alas. Also, there was something awkward about him, maybe it was his height? (he is very tall). I would have thought that someone so handsome would be more at ease, but there was an hesitancy and awkwardness about him.

We got to talking. To my surprise and delight, Dean is a native New Yorker. He actually knows someone I’ve known all my life. And he lived in a neighborhood I know well.

“Oh, hey,” I said, “My friend Jessie lives on your block, in the apartment building on the Southeast corner.”

“I live on the street itself, not on the corner.”

I know my New York City streets. I don’t know that there are any apartment buildings on that block. That could mean only one thing: “Do you live in a brownstone?” I asked.

“Uh huh,” he said, unaware of the effect his revelation was having on me.

Wow: a brownstone. I ordered another drink.

When my Flirtini came I offered him a sip, and when he reached for my drink his hand shook. Again, it seemed at odds with his relaxed slouch and easy conversation. “I’m not looking for a serious relationship,” he offered as we sipped our drinks in the late afternoon sun. I gazed up at the sky. “I just got out of a serious relationship and…”

I nodded. Was this his usual spiel to ward off potential girlfriends or was this a response to me? I couldn’t tell. Did I look like a person who wanted a boyfriend?

“What do you do?” I asked, not really anxious to talk about relationships.

“I’m a poker player.”

“No kidding!” I was pretty sure that on his personals profile his occupation had read “writer.”

He nodded.

“Wow.” I really didn’t know what to say to this. Probably “So, you’re a professional gambler, are you?” wouldn’t go over well, ditto “Oh, did you get caught up in that late 90’s Vince Vaughan – retro – Rat Pack trend? I thought it ended in 2002.” So I settled for, “How long have you been doing that?”

“Not very long.” And with this, Dean edged his chair closer to mine, and slid his hand on top of mine.

Oh! Startled, I took another gulp of my Flirtini. He was bold. Well, sort of: I noticed that his hand was still shaking. I looked up at him.

He leaned over and kissed me.

I mean, I wasn’t complaining, but I’d known him less than an hour.

“Was that too forward?” Dean asked.

Again, I wasn’t really sure what to say. I didn’t mind being assaulted by a cute guy, but we’d skipped the preliminaries, which I so enjoy. To wit: the hand brushing, the shy glances, the admitted embarrassment, all of which I find a prerequisite to an hour or so of drunken making out. I feel that clumsy foreplay adds a certain frisson to the proceedings.

“Well, um… I guess not,” I dithered. “I mean,” I added, anxious not to be rude, “It wasn’t unwelcome, but I barely know you. Did you get the idea that I’m easy?” I asked (I was a little squiffy at this point.) “Cause I am, you know, but…”

Dean laughed, and I looked at my lap and sniggered. Then he kissed me again. He smashed his lips against mine, holding my chin in his hand. What the hell: it was a Sunday afternoon in the summertime. I kissed him back.

“Let’s go to Central Park for a bit and then maybe catch a movie,” Dean suggested after we’d each had another drink and split a quesadilla.

“Well, I don’t know if I can make the movie…” this date was already going longer than I’d planned. Of course, I had nothing else to do but read the new Harry Potter, and I was trying to savor that one, anyway. So I found myself walking to Central Park with Dean. He took my hand. Oh, this was awkward: I came up to about his chest. I’d get a crick in my neck if I looked at him.

We traded memories of our respective New York pasts – oh, how I love meeting native New Yorkers, it makes the feeling of inborn superiority that much sweeter – and eventually ended up on a patch of green in the Sheep’s Meadow. I was feeling pretty drunk, so I sprawled on my back, as did Dean. Was this loose behavior, lying prone in public with a total stranger? Yes, I decided hazily, it sure was.

“I forget if you put ‘Don’t use drugs’ or ‘Prefer not to answer,’ on your personals profile,” Dean said.

“Um, well, I don’t remember,” I said. I had no idea. I don’t really use any recreational drugs (the poppers incident aside), but I didn’t want to eliminate cute boys who happened to smoke weed from my pool of potential boyfriends.

“Ahhh.”

“So, do you…” I mean, did he smoke weed or was he talking about something more exotic?

He was talking about weed. Marijuana had been invaluable to him, he informed me, especially in getting him to appreciate certain aspects of sex that otherwise he had been unable to enjoy.

I gaped at him. “Are you trying to tell me that you couldn’t go down on a woman before you started getting high?” This didn’t impress me. Is overcoming an aversion to oral sex so commendable? I feel men should enjoy going down on women. I enjoy giving head, after all.

“No, I mean...” Dean backtracked. “Before I started smoking, I couldn’t enjoy going down on a woman for itself … I mean, now…”

I snorted. “So now you can enjoy the experience?”

“Yeah.” Dean looked embarrassed. He’d only meant to let me know that sex with him meant lots of eager tongue action.

“Oh,” I sniggered again. “I don’t really get off on oral sex, anyway.”

After a moment Dean rolled on top of me. We lay sandwiched together on the grass. Is this totally inappropriate? I wondered, looking at the people around us. I must be pretty drunk. He kissed me, hard, and then pressed his index fingers along the line of my eyebrows.

“I’m submissive,” I said, apropos of nothing.

“Are you? I like that.”

“I thought you would.” Clearly, I had decided to sleep with this fellow. Well, that’s alcohol for you. Or attraction. Whatever.

A man carrying a plastic garbage bag was hawking beer. Dean hailed him. “Want to have a drink then we can see a movie?”

“Well… OK.”

“I’ve got mojitos!” offered the guy with the black plastic bag.

Mojitos it was. We watched in amazement as instead of presenting us with two bottles, the man proceeded to break out a flask, and then mixed two drinks in plastic cups.

It was getting late; the sun was fading in the July sky. “Come on,” said Dean, “Let’s see a movie.”

**

When we got out of the theatre it was dark at last. “Let’s get dinner,” said my date.

Drinking usually kills my appetite, but what the hell, it was a nice night, and we could sit outside and drink some more and flirt: “OK.”

We walked a few feet to a crowded restaurant and were seated at a table outside. “Put your foot in my lap,” said Dean. I obeyed, and he rubbed my ankle and the top of my foot. Drink made me voluble, and when Dean asked me if I was seeing anyone else, I gave him an edited resume.

“So how many men are you sleeping with?”

“Um…” I counted off: Jefferson, Jed, Jim. three. “No, wait, four.” And Alex. Christ, I must sound like a complete whore. “How many women are you seeing?”

“Well, two, but one of them I don’t see very often. The other one…” I sipped my white wine and nodded my encouragement. “I met her on Craig’s List.” Well, that’s how everyone meets, isn’t it? “And, it’s kind of a situation where I help her with her bills.”

“Oh,” I gulped some more wine. Oh my God! He pays a woman to have sex with him! Actually, I didn’t understand this. Dean was cute and polite and smart, surely he didn’t have to pay to get laid?

“Well,” I said slowly, aware that I was drunk and wanting to choose my words carefully: “I really appreciate you telling me that.”

“We get along well, I mean, I mean, I don’t think she’s faking anything…at one point I said to her, ‘You know I don’t feel that comfortable—“

“Well I’m sure she needs the money!” I said, scandalized. Did he object to paying her? I poured myself some more wine. “Look,” I said when I had fortified myself with yet more alcohol, “I really appreciate you being honest with me about this. But you’re involved with a sex worker. If you want to sleep with me, you’re having an HIV test.”

“Really, I think I’m the only one—”

I nodded vigorously. Maybe he was right. Perhaps I slept with more men than Dean’s part time girl. Maybe I was a worse bet. But. I was drunk and feeling forceful.

Just then our food arrived. For a few moments we ate our pasta in silence, while I digested all this information. This was certainly an informative date. And a long one: it was practically my bedtime.

I pushed my naked foot at Dean’s groin and smirked at him.

“God, you’re sexy,” he said. I looked at my lap, embarrassed and pleased. “And I might have to take you over my knee and spank you for telling me I have to get an AIDS test,” he whispered. “Not that I mind about that at all,” he added in an entirely different voice.

I loved that he had said that: that he had told me he was going to spank me and then in the same breath went on to reassure me that I could demand this of him. I beamed at him. I didn’t know that I wanted him to spank me until he’d said he was going to, but I did, I really did.

When we finished our dinner, Dean suggested we get another drink.

“But it’s late!” It was about midnight. “I have to go home!” He kept talking me into stuff, and I kept enjoying it. Was a taste of our future interactions? Hmmm.

“Listen, I will take you for one drink, and then I will put you in a cab and give you cab fare to get home.”

I chose the path of least resistance, and more cocktails: “OK then. Let’s get a drink.”

We proceeded to another bar where we drank and fooled around until the bar closed. But we were talking a blue streak and I found I had no interest in this date ending anytime soon. We ended up sitting on the stoop of a nearby brownstone, explaining ourselves in an earnest manner. “I don’t fuck around,” I slurred at one point, in between some heated making out. “I mean, I’m honest and I don’t play games.” I’m not sure why it was important for me to stress that. Oh yes, I know why: cause I’d just told him I had a sex blog and given him this address! D’oh!

But finally it was time for me to go. We stood up but when we began to descend the stairs, he or I tripped and we both went flying. I landed next to him on the pavement, having scraped my shoulder but otherwise unharmed. God, how embarrassing. Then I got a look at Dean: “Oh, my God! Are you OK?”

Blood was pouring down his face. Under the amber glow of the streetlamp, I could see that his face was cut in several places. “I’m fine,” he said.

“No, you’re not!” It looked really bad. “Do you have antiseptic, and bandages at your place? Are you sure you’re OK?”

At my insistence we trooped off to a drugstore, and then went back to his place, where I dabbed at his wounds with cotton balls soaked in Bactine. “Are you sure you’re OK? You might be concussed.”

“Really, I’m fine. Come on, let’s sit in the hammock.”

We were on Dean’s deck. He lived in a duplex, and his bedroom opened up onto a terrace. And he had access to the roof above, too. Talk about an embarrassment of riches.

There didn’t seem to be any point in putting up anymore resistance, especially as I didn’t want to, so I followed him up a steep ladder to the roof, where we carefully lowered ourselves into his hammock.

The night was mild and cloudy and when we weren’t kissing I stared at the sky. “Oh sweetie,” Dean whispered, “It’s going to be so good.”

"Mmm," I murmured, kissing the man I'd met nine hours previously. He had several fingers inside me at the time, and I was inclined to agree.