Setting Up Cupid

I was sick of the jokes, and had been for my whole life. When your name is Larry Cupid, every February pretty much anybody I met thought it would be clever to make a joke, as if I hadn't heard every one. And to make it worse, I'm a salesman, so I'm constantly introducing myself to new people every day.

"Gonna find me someone to love this year?"

"Where's your bow and arrow?"

"Are your wings stuffed under that sweater?

Very fucking funny. I couldn't wait for Valentine's Day to be over, because at least the jokes slowed down. This year was no different. Everyone that I spoke to felt the need to make a joke about my name, but because I am generally a nice guy, and a good salesman, I had no choice but to chuckle, as if it wasn't the millionth time I had heard the oh so clever quip.

I love my family, but why couldn't they have changed the name? I know that my dad was teased, but it never seemed to get to him. And to make it worse, apparently it wasn't even the original family name—some moron at Ellis Island decided to shorten Kupidowitz.

I wonder if guys named Scrooge or Claus had it bad at Christmas. That would be great.

And to make it worse, there I was, single on Valentine's Day. It had been nearly 2 months since Tracy had dumped me, not that I didn't see it coming, because things had been pretty tense between us the past few months. But still, it was better to be in a relationship, even a crappy relationship, on Valentine's Day, than to be single.

Now, a smart man would have left work, headed home, ordered in Chinese food and watched basketball, but no, I'm such a nice guy that I agreed to meet up with a bunch of friends at a bar, before they went out on their special dates. Of course, I had agreed to this before Tracy had split, but these were my friends, and so I figured I would go, have a beer or two and then head home. Basketball games don't get interesting until the second half, anyway.

I left the office, took the subway uptown and got to Malone's about 15 minutes late. Bill and Jenna, Alex and Gabby and Markus and Olivia were already there, drinking and laughing. I worked my way through the crowd to their table and squeezed in between Markus and Alex. I couldn't help noticing that the three women looked good, and were dressed for a more interesting night than we were currently having. My friends were going to have a good fucking night, and a good night fucking. Good for them. I had hundreds of cable channels at my disposal and the entire Internet.

After exchanging greetings, man hugs and air kisses, I ordered a draft IPA and pretended to enjoy myself.

It is difficult enough to be third wheel; being a seventh wheel was excruciating, especially since everybody spent the night dancing around the fact that I was single on what is generally considered the most romantic night of the year. It got worse when the soulful voice of Sam Cooke began to sing, "Cupid, draw back your bow, and let your arrow go...." My friends stopped talking and whipped their head around to look at me.

Annoyed, I spat out, "What? I know, my name is Cupid. I've heard the song before, you know."

They all did know, but couldn't help themselves, it seemed. They continued to make uncomfortable conversation, until, one by one the couples headed out to their romantic dinners, leaving me alone. At that moment, Connie Francis' recording of "Stupid Cupid" came on the sound system. I banged my fist hard on the wooden table, causing Alex's empty beer glass to fall off and smash onto the floor.

The waitress came over and asked me if everything was alright, and I lied, saying that it was. I decided to pay my tab and hit the road.

As I was waiting for the check, I smelled, over the beery scent of the bar, a sharp but pleasant perfume. I looked up and saw a blonde woman standing next to me. Being a man, I noticed that she was not bad looking, with a pretty good body. She wouldn't turn heads, necessarily, on first look, but her blue eyes and friendly face would probably grow on you over time.

"Tough day?" she asked in a strong, clear voice.

"Yeah, I guess," I responded, a bit embarrassed.

"Not a fan of Valentine's Day?" she replied, and without waiting for an answer, continued, "me neither."

I figured it wouldn't hurt to ask, so I pointed at the chair next to me and said, "Can I buy you a drink?"

The woman smiled. "I'll join you, but I can buy my own drinks."

"Fair enough," I responded, "please have a seat."

She sat down, and it was clear now that she was shorter than me, and as I looked closer, I thought she was kind of cute and maybe it wouldn't be another crappy Valentine's Day, after all.

"I'm Larry," I offered, sticking out my hand, awkwardly.

"Val," she said, shaking my hand firmly with a small hand. "So, what happened?"

"Happened?"

"Yeah, I saw you pound the table. Valentine's Day breakup?"

That seemed a bit direct. Whatever happened to subtlety, discretion, privacy? I thought, before responding, "um, no, not really. It was a couple of months ago."

"I'm sorry. That sucks," she replied, showing concern on her face.

"I'll be fine," I replied.

The waitress brought us drinks, and Val insisted on paying for the round. I agreed, and promised to pay for the next one.

"So," she asked, "if it isn't the traditional reason why people get angry on Valentine's Day, can you tell me what the problem is?"

"You'll laugh," I replied.

"I could use a laugh," Val responded, but in a way that was funny, not obnoxious.

I smiled sheepishly. "My last name is Cupid."

Val stared at me for what seemed like a minute before breaking out in hysterical laughter. When she caught her breath, she said, "Oh my god, I could see why today really sucks for you."

I nodded.

She continued, "And the music, Sam Cooke, and so on, right?"

"Yeah," I chuckled, "it was Stupid Cupid that set me off tonight."

Val shook her head, "I know what you mean."

Emboldened by Val's directness, I said, "Really, how do you know?"

"Val," she said, pointing at her small, but attractive chest, "short for Valentina."

I nodded. "Right," he responded, "I guess you do know what I go through."

"It gets worse," Val said with a smile.

"How? " I asked, smiling, "your last name isn't 'Day' is it?"

"My parents were cruel, but not that cruel," Val replied with a small laugh. "My last name is Hart."

I could not believe that someone had it as bad, if not worse than me. "Your name is Valentina Hart? Seriously?"

Val reached into her purse and pulled out a wallet, then extracted something and tossed it across the table. I picked up her New York State drivers' license. The picture predictably did not do her justice, but it was clearly her. And the name on it was "Valentina Hart." I noticed that the address was only a few blocks from the bar, which gave me some fleeting hope of taking her home.

"O.K.," I said, tossing back the license. "Either you win the 'bad name on Valentine's Day' award, or you are willing to go very far for a laugh."

Val chuckled, "So, we have something in common. Can I ask you, though, 'Cupid' is an unusual name—"

I interrupted. "Supposedly, when my great grandfather Moshe Kupidowitz came through Ellis Island, they changed it."

"Makes sense," she replied, "but I honestly think I'd rather be 'Larry Cupid" that 'Larry Kupidowitz.'"

"Most of the year, I guess," I responded.

The conversation reached an awkward pause, and we finished our drinks and ordered a second round.

Once that was out of the way, our conversation flowed pretty naturally. We talked about work, a little about our backgrounds, some music and even a little sports. We watched the couples come into the bar, and made up stories about them—the older man with his younger girlfriend, the guy who furtively checked out every other woman in the bar and ignored his date, the mushy couples trying hard to live up to the Valentine's Day pressure. About three rounds in, we actually got to see what looked like a woman breaking up with her date, from the look on his face right before she put on her coat and walked out of the place, and the fact that he appeared to order a number of amber colored shots, which he downed quickly and joylessly.

Val excused herself to go to the ladies room, and I checked my watch, surprised that it was already 11:30, and even more surprised at how much I was enjoying this usually annoying day. I realized that it was about to reach the critical moment, where I would ask for her phone number, or try to walk her home for the proverbial nightcap, and I would find out exactly how good a Valentine's Day it was going to be.

When she came back to the bar, before I could say anything, Val said, "Larry, this has been nice. You seem like a nice guy. Can I have your phone number?"

That seemed pretty promising, so I offered to call her cell, but she insisted that I write down the number on a bar napkin, which was less promising, but not unreasonable, considering we had just met. I had such low expectations for the night that it didn't bother me that much—I definitely would have called her for another date, but if she wasn't interested, I wouldn't kill myself.

She put on her coat, so I did the same, and walked her to the door. "Thanks, Val," I said, "for helping to make what usually is my least favorite day of the year fun."

"Thanks for everything," she said, reaching her face up and kissing me on the cheek before heading out to the street. Having nothing better to do, I followed her out and started to walk to the subway.

I have to admit that over the next few days, I kept hoping that she would text or call me, and kept checking my phone, in vain. And by the following week, I had pretty much moved on, figuring that she wasn't interested. So, I was surprised to get a call from her one evening while I was watching one of my favorite sitcoms.

"Larry, it's Val," she said.

"How've you been?" I asked, trying to keep my voice flat.

"Good, and you?"

"Pretty good, I guess," I answered truthfully. My bad day had passed, and I had made a couple of pretty good sales at work.

"This may be a little weird," Val started, "but I have a friend that I would like you to meet."

That was unexpected. She liked me enough to set me up with a friend, but not enough to go out with me. It was both flattering and a little annoying. "Really?" I asked, "that is a little unexpected."

"I know, trying to set Cupid up on a date...." she started, trailing off when I didn't laugh.

"Yeah, thanks," I said, disappointed that she of all people would trot out another line that I was quite familiar with.

"So," she asked, "are you interested?"

"I don't know, tell me about her."

"She just joined my company a few months ago and is really nice and pretty. Tall, skinny, nice figure, blonde hair. She seems really smart and has a good sense of humor. . ."

There were as many red flags in that description as there were lures, but I'm a nice guy, so I figured, what the hell.

"Sure, why not?" I responded.

"Great—I'll give her your number, and she can call you to make arrangements."

"That's fine—what's her name?"

"Oh yeah, you will probably need that," she laughed. "Sherry. Sherry Wine."

It was my turn to laugh. "Really?"

"Yeah. I figured if anyone would be sympathetic to her name issue, it would be you, Larry. And I thought you were a nice guy who would get along with Sherry."

"Sure, I'm sure it will be great." I paused and figured, what the hell, before continuing. "Val, can I ask you something?"

"You want to know why I'm setting you up with a friend when we had such a good time the other night, right?"

"I knew you were smart," I said. "So?"

"I wasn't completely honest with you. I was at the bar to meet my boyfriend, and he got stuck late at work. I was already at the bar, and figured I would have a drink. Then you offered me a drink, we had the bad Valentine's Day connection and you were a nice guy and it was fun. But I'm in a relationship and happy, so it wasn't going to go any further. But I thought Sherry might be a match for you."

I was a little disappointed, but realized that Val had never been anything but honest with me—I never asked her if she had a boyfriend, and she never really led me on. And maybe my date with Sherry would be fun. "I appreciate your honesty, and if you endorse Sherry, I'd love to go out with her."

Sherry called me the next day and we made plans to get dinner on Friday. She sounded nice, if a little shy, but perfectly pleasant. Friday rolled around as it does every week, and as we agreed, I met Sherry at a small Italian restaurant in the non-touristy part of the Village that she suggested. I was early, as usual, and was having a beer at the bar when a tall, slim blonde walked in. When she took off her coat, I could see that she was wearing a skirt, blouse and blazer, looking like she came straight from work. My first impression was that she was attractive, if not head-spinningly beautiful, but assuming that it was Sherry, I wasn't prepared to sneak out and stand her up based on appearance alone. Not that I would do that.

She looked around the restaurant looking a little uneasy, and I stood up and walked over to her. "Sherry?" I asked.

"Yes, Larry?" She asked, sticking out her hand.

"Yes," I responded, shaking her hand, and noticing that she had a strong grip.

Dinner was excellent, and the conversation was fine, if a little labored at first. Sherry was, as advertised, nice, smart and had a subtle, cutting sense of humor. I liked her, although I didn't feel that same easy rapport that I had with Val. But it was also just a first date, and a blind date at that, so the fact that it was enjoyable at all was a plus.

After coffee, we left the restaurant, and although it was a cool February night, there was little wind, so that it was comfortable to walk and without discussing it, we walked through the streets of the Village chatting, puffs of fog escaping our mouths.

It didn't seem like we were heading any place in particular, but Sherry stopped in front of a brownstone building and said, "This is mine."

I was about to say good night and tell her that I had a good time, when she asked, "Would you like to come in?"

Why not, I thought. It was not the best date I had ever been on, but it was far from the worst, and I was enjoying Sherry's company, so I said, "Sure."

I followed Sherry up the stoop and waited while she fumbled in her bag for the keys and opened the door. I expected that the building would be subdivided into a number of apartments, but was surprised to walk into a wood paneled entrance hallway that opened into a central room that had a staircase at the back, and doorways to rooms on both sides.

"This is all yours?" I asked, surprised because nothing in Sherry's manner, or her description of her job, indicated that she could afford to own her own brownstone in one of the nicest neighborhoods in New York.

Sherry looked a little embarrassed and said, "It is. I grew up here, and my parents passed away a few years ago, leaving me the building, not to mention enough money to pay for it. It's really too much for me alone, but I love it and could never sell it."

"I'm sorry about your parents," I said.

She shook her head. "It's O.K. now. But it really isn't good first date conversation, is it?"

I nodded and appreciated the way she handled the issue.

"Take off your coat," she said, and I obliged. She took it and hung it up in a coat closet that looked to be half as big as my bedroom.

I think that she saw my fascination with the house, so Sherry asked, "Would you like a tour?"

Of course, I said yes, and she started off showing me the downstairs rooms, including a beautiful kitchen and a library filled with more books than the shelves would hold. I followed her upstairs and she showed me the bedrooms, including the one that had been her childhood room, all of which seemed bigger than my entire apartment. She opened a door that could have been a closet, but which turned out to be another staircase, and I followed Sherry up the stairs into a master suite that filled the entire floor. It was decorated in a restrained modern style that was both functional and attractive. I looked around the room, and when I turned to look again at Sherry, she was unbuttoning her blouse, giving me a glimpse of her fair skin and the bra that enclosed her small breasts.

I honestly had not expected more than a drink, or a cup of coffee, but I was certainly not going to reject the advances of this attractive and interesting woman. After she had finished unbuttoning her shirt, I stepped toward her and pulled her close for a kiss, which felt very nice. Within a very short time, we were naked and in Sherry's large, comfortable bed, exploring each other's bodies. Sherry wasn't my usual type—I generally went for shorter, curvier women—but Sherry's body was really flawless. She had virtually no body fat except where you would want some, and I found out that night that she was a particularly talented and attentive lover who enjoyed both giving and receiving pleasure. Which is a nice way of saying that in that bed, she totally rocked my world, to use a cliché, and if her screaming my name was any indication, I had a similar effect on her.

I woke up the next morning, naked, thirsty and sore, lying next to Sherry, and in the morning light, her body looked even better. I watched her breathe for a while before getting up to use the bathroom, take a drink and splash a little water on my face. I was not the most experienced guy in the world, but I had been with a few women in my life, and there was no question that was the best sex I had ever had. And there was a big gap between that and second place.

When I returned to the bedroom, Sherry was lying, nude, uncovered, on her back, her long legs spread, and her trimmed pussy appearing to be waiting for my attention. I touched her between the legs and she sighed, so I began to rub harder. She reached out and took my hand, pulling me toward the bed, and I landed on top of her prone body.

The next thing I knew, I opened my eyes, it was after noon, and I was exhausted. Sherry was nowhere to be found, so I got up, took a quick shower, dressed and went downstairs, following the smell of coffee to the kitchen. Sherry was there, her hair wet apparently from a shower that she had taken while I was not conscious, wearing a robe, drinking coffee from a mug. She smiled at me and said, "Coffee?"

"Yes," I croaked, "please," and she poured me a mug of the steaming brew. I added some sugar and milk and took a deep swig. I then noticed that there were fresh bagels and cream cheese on the center island, and I realized that I was famished. We ate breakfast and made small talk, and after we cleaned up the breakfast disthes, I turned to Sherry and said, "I want you to know that was the most incredible sex that I have ever had."

She smiled, and her face lit up. "It was pretty amazing, you were amazing."

It was my turn to smile, and as I did, she walked past me and started walking up the stairs. I had a pretty good idea why, and I followed her up to her room. She took off her robe, confirming my suspicion that she was naked underneath it, and within seconds, I was also undressed, and we were going at it again.

Over the next few weeks, Sherry and I spent an incredible amount of time together. Dinners, either out or in, followed by mindblowing sex. There wasn't anything she was unwilling to try, and she pushed me to try things that I never would have considered. She was also a clever conversationalist, quick with a joke, and never took offense when I kidded with her.

During early May, Sherry was sent out of town on a business trip, and I realized that it had been a long time since I had a guy's night with my friends, so I made arrangements, and met up at Malone's with Alex, Bill and Markus.