Heading into Valentine's Day, I had a pretty good idea of how I wanted to spend my evening: generally inert. To me, at the time, it seemed that the best possible course of action for a single, slightly disillusioned and supremely broke young man such as yours truly was to park myself on one of the stools at our neighborhood hipster bar and ogle the Shakira-lookalike bartender onto whom I've projected my affections. I realized that it might not be the most impressive Valentine's Day night out, and that my subsequent chances of Valentining a foxy young lady were effectively nil, but after a string of messy drinking nights and messy drinking nighttime companions – an inspired run that led observers to remark, "Aren't you getting a bit old to act like this?" and myself to reply, "Gnuhhhh banana Hamlet" before puking everywhere – all I wanted was a low-key night to steady the course of my ship.

But that was before provocateur naturelle Alex "Voetsch" Voetsch came along with his set of Valentine's Day plans: romantic schematics featuring an activity so rich in story potential that I promptly forsook my own lame agenda. Hearing them, I decided – alongside companions Susan B., TBone, Basil and Lesch – to follow "Voetsch" uptown, where we would be attending a handcuff party. The rules were simple: Ladies were given handcuffs upon entering the bar, and guys couldn't partake in drink specials unless they find a gal to bind herself to them. Though my original plan to wallow in self-pity at a local bar was enticing, nothing says "romance" quite like "Voetsch" handcuffing himself to aesthetically challenged women just to score cheap booze.

9:15: I arrive at the bar in midtown Manhattan. I turn a few heads upon entering, though my initial elation is tempered by the knowledge that people are looking at me because I'm wearing red polyester pants and a matching tie. I think I hear someone, possibly from my own entourage, call me a douche.

(Related tangent: the term "douche" has pretty much completely worked its way into the tween-aged lexicon, though this fact has somehow eluded anyone over, say, thirty. Never was this more apparent then when I referred to myself as a "douche" in a work email to all my editor-associates the other day and received responses that ranged from light-hearted amusement to complete disbelief that I would reference a female hygiene product in a work email that included women. Will "douche" ever catch on with the older set? Will I keep my job? New developments to be charted.)

9:30: "Voetsch," the evening's mastermind, suggests that we get some Valentine's Day cards from a nearby pharmacy and hand them out to gals in the bar. I make an impromptu run to Duane Reade for ammo and find a disheartening lack of VDay cards for 9:30 at night on the big day. I end up going with two bags of Spongebob Squarepants lollipop cards, which cost $2 for bags of 22. Bitches better respect.

9:35: The fellas scramble for lollipops when I return. "Voetsch" and I allocate a handful of the "You're My Best Friend" variety to the guys while keeping a bulk of the golden "You Steal My Heart" cards for ourselves. The lollipops are shaped like hearts. These are more of a lock than roofies.

10:12: My crew and I station ourselves in the front corner of the bar, as is the textbook M.O. for a roving group of young men, and begin handing out cards to women within our attack radius. A problem quickly develops: Turns out that when you're in a bar packed with four hundred dudes and seven gals, it's difficult not to hit on the same gals as your buddies. It also turns out that when you hand a babe a Spongebob Squarepants Valentine's Day card, she will think it's an adorable gesture . . . unless two members of your group already gave her the exact same Valentine in the past fifteen minutes. Then it's not so adorable. Noticing our lack of range, "Voetsch" and I embark for a corner at the far end of the bar, hoping to unearth a new trove of girls to bombard with redundant lollipop cards.

10:22: The following exchange takes place:

"Voetsch:" I want to give that girl in the sweater a card.
Me: So do it.
"V:" But she's not that hot, is she?
Me: Not especially, no.
"V:" But I'm sure it would really make her night.
Me: It absolutely would.
"V:" What if I just give it to her and run?
Me: . . .

Ultimately deciding to do just that, "Voetsch" leaves me standing in The New Corner. I occupy myself briefly by watching the two worst dancers in the history of mobility 'n' rhythm bash genitals with each other; then, a thought hits me: Who is more pathetic: A pair of drunken revelers dancing like crippled giraffes, or a lone dude standing there mostly sober watching them? Fortunately a hot babe walks by at that very moment, and though I don't talk to her, it diverts me from my previous line of thought and ushers in a new one: How much do escort girls cost? Are they clean? Is there a Valentine's Day discount? Or do you pay a premium? What if I wait 'til after midnight?

10:30: To date, I have yet to see a handcuffed couple. This is disappointing, as my night's expectations were based around getting one of my louder associates – "Voetsch," Susan B. or Chris, ideally – attached to a heifer and watching him inadvertently offend her as he yelled complaints to us.

The terrible dancing duo is now a destructive force in the back of the bar, as they've switched from close 'n' intimate – albeit awkward – grinding to some distant, retarded cousin of swing dancing, and they now pose a threat to anyone who comes within fifteen feet of the area. Standing just inches from ground zero I brace myself for the worst, which comes seconds later when "Voetsch" enters the area only to get wrecking-balled.

10:50: One fleet of my crew just left for another bar, and the remaining three of us – "Voetsch," Susan B. and I – are about to mobilize when we encounter an obstacle: an errant drunkard snares "Voetsch" with her cuffs and drags him to the bar for rounds of discounted shots. In all fairness, the handcuffer is cute; in all honesty, she is the only attractive girl in her group of four, which clearly conforms to the established female clique-hotness-ratio guidelines. Susan B. and I retreat far, far away and watch the situation unfold.

10:51: The situation unfolds and re-folds in seconds. "Voetsch," sated by discounted shots and terrified by the zoo he found himself in, breaks free from his captor – despite her really, really impassioned pleas – and our trio heads outside. There we find the hot babe that passed me a half-hour ago, and engage her in brief discussion. She compliments my pants, thanks Susan B. for his many thoughtful, identical Valentines Day cards and asks when we'll be back to the bar. At this point "Voetsch" and I realize that she's a paid employee of the establishment, while Susan B. becomes convinced she's coming onto him. Using the baffling tactic he's employed of late, he immediately asks her out to dinner; she replies with the suggestion that the three of us come back to the bar the following night to see her. Susan B. looks at "Voetsch" and I with the, "Hey, let's do that" look. We, in turn, hail a cab.

11:09: In the cab to another bar, "Voetsch" explains his poker metaphor for dating:

"You have to wait for a good hand. I obviously won't play 2-7 off-suit. At very least, I need king-8 suited, and that's when it's late and I'm desperate. In normal conditions I wait around for K-Q suited before I play a hand. Maybe I'll see a flop with that hand, hang around for the turn, y'know. What you really want to see is that pair of pocket aces, though how often does that happen? Smaller pairs are a crapshoot. A 2-2 might hold up – maybe she has a good personality, maybe a cute laugh, something like that – but it's really not a very good hand. It'll win once in awhile, but most times you play it you'll wake up the next day with a fat chick who has a scathing case of herpes but can tell a good joke. You just shouldn't chase hands like that. In the long run, you're going to lose."

11:21: We arrive at the new bar and find it emptier than Rick Moranis's day planner, prompting a round of finger-pointing and invective-hurling. Though fellow struggling writer Molly Knight is waiting tables, the barren bar is more of a downer than some of us are prepared to handle. Half the crew decides to stay, "Voetsch" and I decide to leave and Susan B., drunk beyond the point of decision-making, teeters near the door.

11:45: En route to the next bar, "Voetsch" and I make an executive decision to get some Dominos pizza; then, while enjoying a delectable $9.99 large pepperoni pizza, we erupt into a feverish discussion about the situation in the Middle East with the Islamic cartoons and Danish newspaper""as so often happens in Dominos pizza pick-up-only establishments across the world. We leave when the employees start to look at us funny.

12:20: "Voetsch" and I arrive at the same bar I had intended to visit in the first place. We grab some beers and mosey down to the pool table, where another discussion develops; this one about whether or not it's preferable, at our age, to have a steady girlfriend. Blatantly ignoring the situational influence of having this talk on Valentine's Day, we determine that yes, it is far more advantageous to have a girlfriend. We fail to explore whether or not we, as single 24-year-old guys who are decidedly not getting laid on the day that single girls are most jaded and willing, are essentially choosing to take a cyanide pill while in captivity rather than endure torture.

1:00: After a thrilling round of games betwixt the two of us, "Voetsch" and I are approached by two less-than-desirable females and challenge to a pairs game, with the losers buying the winners drinks. We punctuate our agreement with an almost maniacal laugh, and then proceed to very nearly lose. [Conscience's note: We actually did lose, when I scratched on the 8-ball, but the girls played on and "Voetsch" gave me a "shut the fuck up" look.] For the next game, the girls propose that we "mix things up" and form co-ed teams, which we suspect was their plan all along. I get paired with a confident and healthy-in-the-Victorian-sense gal sporting a dress that made her look like Andy Warhol painted a mountain. (Not painted a mountain on canvas, mind you, but actually hauled some tankers of acrylic paint out to the Catskills and spent a month slopping paint all over a modest hill. As associate TBone would later say, "Wow! That . . . that is a dress.) Immediately, the following exchange takes place.

Her: Oddly dramatic: Tell me about yourself. I want to know everything.
Me: Wow, that's very forthright of you. And dramatic.
Her: Well, I'm an editor, so I have an eye and ear for such things.
Me: Ah.
Her: And what do you do?
Me: I'm a struggling writer.
Her: Oh, that's noble.
Me: Yeah.
Her: Do you do anything else to support yourself?
Me: Not really, no.
Her: I don't know how you get by. I'm a Columbia MBA student, an editor for a famous author and a bartender, and I can still barely get by.
Me: Yeah, it's . . . uh, it's tough.
Her: Well, what's your last name?
Me: Janowitz.
Her: Neil Janowitz? I've never fucking heard of you.

At which point I reach for my notebook and pen and think to myself, "That's probably for the best."

1:37: Having grown weary of my pool partner's never-ending list of credentials, I slip over to the bar, where I find Shakira-lookalike banging away with some drumsticks in front of two gentlemen, who are clearly also drummers. Being something of a percussionist myself, I sit down and the four of us pass the sticks around like a joint, banging out our favorite rudiments. It is an odd, odd scene. But as I sit there on a bar stool, letting Shakira-lookalike's ratamacues blend into the dangerously unnatural beat of my heart, it hits me""my night ended up just as I planned: On a stool, single, disillusioned and broke as hell. Yet, somehow, I feel pretty damn good about the night. The pre-VDay ennui that had afflicted me is gone. Warhol's Lost Masterpiece walks up behind me and says something about buying her a drink, but I keep drummin' right along with Shakira-lookalike, who, admittedly, only resembles Shakira if you're in an extremely low-light situation and are Ray Charles. But sometimes, on Valentine's Day like any other day, you can't be upset about not walking away from the game with more chips than you started. You just have to be happy to have played one winning hand.

And if you can get your buddy handcuffed to a werewolf in the process, well . . . that's just icing on the metaphor.

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Neil's a struggling writer with an email address. He likes subwoofers. No, he loves them.