Setting Up Cupid

After the obligatory man hugs and joking insults, we ordered a round and caught up. They were happy to hear that things with Sherry were going well, and it seemed like they were all happy in their relationships. Markus tried to convince me that maybe I shouldn't be so negative about Valentine's Day, but I told him that it was a pretty weak argument to tie my relationship with Sherry to my meeting Val that day. I said that as long as people insisted on making stupid Cupid jokes, I'd hate Valentine's Day.

Of course, all of my friends were whipped, and one by one, they made excuses to leave and get back to their women. I figured that I'd go back to my apartment, which I rarely visited these days, and watch a little TV before bed, when I saw Val walk in the door. I hadn't seen her since Valentine's Day, but I owed her at least a thank you and a drink for setting me up with Sherry, so I waved and got her attention. She smiled when she saw me, and sat down in the chair that I gestured to.

"My boyfriend is meeting me here, and I'm early, so I can sit with you until he shows up," she said, getting right to the point, a characteristic that I appreciated.

"I just wanted to say thanks, and buy you a drink for introducing me to Sherry," I said.

"I'll take you up on that," she smiled, and I noticed that she seemed to be more attractive than I recalled from our last meeting. "I hear from Sherry that things are going well with you."

I must have had a real shit-eating grin on my face, because Val said, "Sherry has that same look on her face when she talks about you."

"I will say that she is an amazing woman, but a gentleman doesn't kiss and tell."

Val smiled and said, "Well, if the same rules are supposed to apply to ladies, then your girlfriend is no lady."

I felt my face get warm, and assumed that it was bright red. Val chuckled and said, "You should be proud, not embarrassed," and I shrugged bashfully.

We ordered our drinks and had a great talk until Val's boyfriend Sasha showed up. He was a tall, handsome guy who looked to be a few years older than us, and had a slight Russian accent. Val introduced us, we shook hands, and I made excuses and headed home. As I walked to the subway, I thought about how strange things were—it was clear to me that Val and I had some chemistry, but because she was seeing someone, she introduced me to Sherry, and now I was in a great relationship with her, and not Val.

I got home, changed into sweats and started watching TV when my phone rang. It was Sherry, calling from the hotel in Indianapolis, and we caught up. I told her about my meeting Val and her boyfriend, and she suggested that the four of us should go out, which seemed like a great idea. She then told me that she was naked, and described, in detail, exactly what she was doing to herself and what she intended to do with and to me when she came home in two days. I'd never had phone sex before, and it was pretty incredible.

When we had both reached satisfaction, Sherry said good night. I cleaned myself up and went to bed.

Sherry returned a few days later, and we picked up where we left off. But as much as I enjoyed the sex, and I did, and her company, there were times that I felt like something was missing. Those thoughts were fleeting, but never totally out of my consciousness. For her part, Sherry seemed happy, and I was glad that we were having fun, and that there were no signs, at least any that I could see, that Sherry wanted to move our relationship to any other place.

A months after her business trip, we went out for dinner with Val and Sasha. Sasha turned out to be a pretty fascinating guy, a computer genius who had moved here from Russia as a child and had serially started a number of Internet companies, selling them for increasingly obscene amounts of money. And as always, I enjoyed talking with Val. In fact, I had to admit that at one point, she and I were chattering away and I noticed both Sasha and Sherry looking bored. I forced myself to engage Sherry, and things proceeded well after that.

Later that night, when we were in bed, Sherry said, "You and Val seem to get along really well."

Being an idiot, and not thinking, I responded, "Yeah, we seemed to hit it off right away."

A somewhat dark look passed quickly over Sherry's face, which changed into one that usually meant something good was about to happen to me, and she said, "Well, do you think that she would do this to you? And she commenced to do something with her mouth and a finger that shortly brought me to a screaming, trembling orgasm.

After I had tried with some apparent success to repay Sherry's kindnesses, I lay there thinking and wondering about what it would be like if Val, in fact, did that thing, and I smiled to myself before dropping off to sleep.

Unusually, Sherry's ardor did not seem to wane, and we continued to fuck like bunnies, but also spend time doing other non fucking things together. While it was mostly very enjoyable, sometimes it was like I had a small stone in my shoe that increasingly would, out of the blue, cause me discomfort. I tried to confide in my friends, but, to a man, they fell back on the standard responses—you enjoy her company, she is good looking, the sex is great, why would you want to rock the boat?

It bothered me, though, because I figured the longer we were together, the snowball careening toward a permanent relationship would build up speed, and I would find myself, in a tuxedo, with a face covered in wedding cake before what would certainly be a honeymoon not to be forgotten. And some days, I would kick myself, because most people never find anyone who is even close to perfect, and Sherry was certainly close. But you know what they say about "close," and I hated that it bothered me so much.

One evening in January, I went to Sherry's office to pick her up before dinner, and she had just gotten a call from a client and needed to do some hand holding. I sat in the office reception area checking my phone, when Val came out, presumably on her way home. It was unseasonably warm, and she was wearing less clothing than any of the other times that we had met, and I had to admit she was pretty striking.

"Hey Val," I said, and she turned her head and smiled at me.

"Larry, why are you waiting here?"

"Sherry and I are going out to dinner, but she got a call and had to take it."

"Sorry to hear that. I'm going to meet Sasha at Lucky Peach—you guys should join us."

I had always wanted to try it, but we had never gotten around to going there, and I figured it would be fun, so I said, "O.K. with me, but I'll have to make sure it's O.K with Sherry."

"Call me on my cell when you know, and I'll let them know."

"Fine," I said, more excited than I should have been, and I enjoyed watching Val walk to the elevator, her hips swaying seductively in her tight skirt.

A few minutes later, Sherry came out into the reception area, looking very cute, as she usually did.

After we kissed, I said, "I ran into Val on her way out, and she and Sasha are eating at Lucky Peach, and asked us to join them." I noticed a flicker of something pass across Sherry's pretty face, but thought nothing of it.

"Um, sure, that would be great," she said, and I believed her. I called Val and told her that we would be there in a few minutes. Taking Sherry's hand, we walked to the elevator, left the building and grabbed a cab to the restaurant.

When we arrived, Val and Sasha were sitting at a table for 4, and I sat down across from Sasha, with Sherry on my left and Val on my right. Conversation flowed along with wine, and the food was amazing. I ate combinations that seemed to make no sense until you put them in your mouth and then the chef's brilliance was demonstrated. I was having a great time—Sasha was interesting as always, Val and I chatted effortlessly, and Sherry was her usual clever and funny self.

Right before dessert, Val's leg accidentally brushed against mine, and I drew back as if I had touched a hot stove, almost falling out of my chair. Everyone looked at me, and I whipped my head around, making eye contact first with Sherry, then Sasha, and finally with Val, whose furrowed brow indicated to me that she understood that her touch was what caused my reaction. I couldn't stand her gaze and looked back at Sherry, who had a blank look on her face. I stammered out some stupid excuse and pulled myself together. We made it through dessert without further incident, paid the check and headed out.

My head was spinning. I always knew that I had some sort of rapport with Val, but that had been electric, and I didn't hear Sherry right away.

"Are you O.K., Larry? You've been acting strangely all night."

I tried to gather my wits, and said, "Yeah, it's all good. Just trying to figure out why I lost my balance in there."

Sherry looked at me and I thought she was going to call bullshit on me, but instead she turned and hailed a cab. The ride to her place was quiet, and when I looked at Sherry, she was looking out the window, pensively, and I watched her as the lights flashed, alternating light and dark as we hurtled down the avenue.

And that night, although Sherry's desire for sex seemed unaffected, I thought that maybe her heart wasn't really into it, or maybe, in retrospect, it was my heart. But the next morning, things seemed back to normal.

That night, though, as we sat on the couch, watching television, Sherry looked at me and said, "Larry, where do you see this going?"

The time had finally come, it seemed, to define the relationship. As much as I was enjoying it, we were both at the age and time of our lives where people were either getting married or moving on. Sherry was entitled to that, and to be fair, I was happy, and could see being happy with her for years. But I wasn't sure about it, and the thing with Val was certainly troubling. On the other hand, she was happy with Sasha, and was it worth blowing up my relationship with Sherry for the minute chance that something would someday happen with Val? I realized that Sherry was staring at me while I was thinking.

"Larry, are you there?" she asked, with an edge to her voice.

I decided quickly that a version of the truth was needed, and I said, "I'm very happy with you, and I hope you are with me. And we should think about the future."

That non-answer answer seemed to satisfy her for the time being, and she cuddled against me and we watched TV for a while before going to bed.

Unfortunately, my promise to think about the future seemed to set Sherry off, and over the next few weeks she dropped hints, some subtle and some more blatant, that something needed to be resolved, and soon. And, it appeared, preferably by me giving her a diamond ring.

I thought about it, and even priced a few rings, without much enthusiasm. I could see myself married to Sherry, but I wasn't ready to be married to Sherry. It wasn't that I needed to know her better—I was satisfied that I knew her well enough to realize that she would be an amazing wife and, should we go down that road, an incredible mother. But I just could not pull the trigger.

Of course, Valentine's Day was approaching, and it was shaping up to be another disaster. Not only was I getting the usual "Cupid" crap from everyone, but it was clear that Sherry expected me to propose. I came very close to buying a ring once—I even had one picked out and my credit card in my hand, but got cold feet and walked out of the store instead. I walked the windy streets of New York and decided that I owed it to Sherry and to me to tell her the real truth, and let the chips fall where they may. Best case scenario, we would stay together and take more time to decide whether we wanted to make a lifetime commitment to each other.

I had made reservations for dinner at our favorite French restaurant, and Sherry looked phenomenal, and there was a light in her eyes that was extraordinary. Which worried me, because I knew that I was going to disappoint her. As usual, the food was excellent, the wine perfect and the conversation was great. Before we ordered dessert, I decided that it was time. I cleared my throat and said, "Sherry, this has been an incredible year. You are an amazing, beautiful, smart and funny woman, and have been an incredible girlfriend."

I could see her smiling at the compliments, and I continued, "I know that you want to know where we are going, and I think I know what you want." Sherry's smile had disappeared, replaced by a questioning look. I had no place to go, though, but forward. "I think that someday, you and I could think about marriage, but I want to be honest with you—I'm not ready yet. And if you will bear with me and give me more time, I hope we can get there."

Sherry's questioning expression turned to anger, then sadness, then back to anger. Through clenched teeth, she hissed, "Are you serious? After everything I have done this year? You need more fucking time? Not going to happen." She stood up sharply, took a step away from the table, turned and said, "Don't bother coming to my place. I'll ship your crap to you."

I felt everybody's eyes on me. I sat there quietly for a few seconds and realized that I had now added a public breakup to my reasons for hating Valentine's Day. I began to laugh, first quietly, then louder, until I was nearly convulsing. When the spasms stopped, I noticed our waiter hovering over the table.

"I assume that you will want the check, sir?" he asked calmly, as if stuff like this happened every day.

Which seemed hysterical to me, so I laughed again and said, "Yes, please."

When he returned, I gave him my credit card. When the final bill came, I added a nice tip, signed the receipt, got my coat from the coat check and headed out of the restaurant. I started to walk to the subway to my apartment, but decided that I needed a drink. And I figured that Malone's was as good a place to go as any, so I changed directions, went to the station and took the train uptown.

In the few blocks between the subway exit and the welcoming doors of Malone's, I must have passed a dozen couples, holding hands, kissing, and generally looking happy. I, of course, was seething. I knew that I did the right thing for me, at that moment, but there was a nagging doubt in the back of my mind that I had not made a good long-term decision. I opened the door to the bar, and, as expected, it was mostly filled with couples, or groups of couples, on Valentine's Day dates.

I pushed my way through the crowd and wedged my way to the bar and ordered a Maker's on the rocks. The smoky sweetness of the bourbon burned when it went down, but then caused a pleasant warmth to spread up from my gut. It felt better as I drained my first glass, so I ordered another. I was about two sips in when that fucking Sam Cooke song came on again, and without really thinking, I slammed my glass against the dark wood bar and said, louder than I should have, "Fuck. Not this again!"

"Seriously?" I heard a familiar voice say, and I turned around to see Val, dressed to kill in a form fitting black dress that hugged her curves.

"What are you doing here?" we said at the same time, and laughed. She put her hand on my arm, and I felt that electricity again.

"You first," I said.

Val shrugged and said, "Sasha and I went out for dinner, and after the appetizer, he mentioned that he had found what he called an irresistible opportunity to move to St. Petersburg—the cold one in Russia—and run a big Internet company. He wanted me to come along."

"That was nice of him," I said.

"Yeah—I should move thousands of miles to a country where I don't know anyone, and don't speak the language and give up my job which I love. Real nice," she said, scowling. "But I was mostly pissed off that he had made these arrangements without ever discussing them with me. I told him 'Do svidanya' which is pretty much the only Russian I know, and walked out. And what happened with you and Sherry?"

I paused, realizing that the situation had changed before saying, "Ever since that dinner that the four of us had, Sherry has been pushing me to, you know, define our relationship, to," I made finger quotes, "'move things forward'. I knew that she wanted me to propose, and I wanted to make her happy. But I couldn't do it. It was clear that she expected me to do the whole kneel and propose thing tonight, but instead, I asked for more time."

"Ouch," Val responded.

"Yeah, that didn't go over too well. And she walked out on me." I raised my glass and took a swig of the fiery amber liquid. "So, here I am."

"But you guys seemed so happy," Val pressed.

"I was. She was...is... an amazing woman. But I obviously had doubts, I guess, or I would have closed the deal, as we say."

Val looked at me, and I noticed how blue her eyes were. She said, with a wry smile, "just another man afraid of commitment, I guess."

I shook my head. "No, I'm not afraid of commitment—just afraid of committing to the wrong person. And I wasn't sure that Sherry was the right person, and I wouldn't want to go down that road, and hurt her."

There was an awkward silence as we both drank and looked at each other. For some reason, the loud bar seemed to be silent, and I realized what I needed to do. I put my hand on Val's arm and said, "To be completely honest, I couldn't stop thinking of you."

Val's eyes opened wide and she said, in a low voice, "You felt that too?"

"Like a cattle prod in the gut."

She tilted her head up, and I leaned over and gently brushed my lips over hers. The small sigh that escaped her mouth was about the hottest thing I ever heard, and she melted into my arms. I held her tightly, feeling the warmth of her body and the firmness of her breasts against my chest. Her hair smelled floral, and I closed my eyes and buried my nose in her golden tresses.

Val looked up again, and I kissed her, for real this time, and felt shivers down my back. When we disengaged, she was breathing hard and said, "Well, Cupid, that's a bullseye."

And for the first time, I didn't mind the joke.