Dear Penny,

I'm brand new in town, and was wondering where the best places to meet young people like me are. I'm a 24 year old buoyant blonde and a big Sox fan, with a bubbling personality to match!

Loves, Trista


Sometimes, the city of Boston can make me feel incredibly stupid. Not just because it has a good hundred years on me (and, as my mother would say, "Age before beauty, Penny") nor the fact that it's greatest export is a fluid mixture of scholastic genius' and rabid sport fans, but because every time I step one foot outside, I immediately feel like someone I'm not. For instance, take me and my friends on this particular Saturday night: the Astros are in town, leading 4-3 three blocks away. The Celtics are having an exhibition game nearly next door to my friend Julia's apartment, and instead, the three of us are in a sports bar. Dressed to kill, but in Rad Tad's Sports Bar and Grille instead of anywhere we should be.

"I hate this place," Julia complains, picking up her Heinekin bottle and swirling the remaining contents around it like she were a sommelier in a previous life. Her dark curly hair has been frizzed out, thanks to both the bar's complete lack of air conditioning and the presence of 50+ sweaty, angry men in a 30 foot by 30 foot room. Julia is exactly twenty-seven years old and not a day past. If she was even a millisecond older, the black glittering halter top she wears would be entirely inappropriate for a woman her age, according to her mother, Harriet. Harriet calls Julia twice a day to ask why she isn't married, and twice a day Julia lets her cell phone accidentally go to voicemail. "Tell me again why we just didn't go to the game?"

"We went to the Red Sox game last week," Daphne replies, pulling her Kate Spade Chinatown purse up to her lap. After fiddling with the opening, she plunges her hand into the silk interior and unearths a compact, with which she begins examining her own red hair, most likely to reassure herself she looks at least 15 better than Julia. Daphne is twenty-nine, and her mother could care less what Daphne wears when she goes bar-hopping on Saturday nights. This is probably because Daphne's mother is nearing sixty, and I am 90 sure Julia has borrowed her top from her. "Anyway, I don't have enough money to go to the Laundromat yet. Besides, do you really want to wear the same grungy baseball jersey 2 weeks in a row? What if that cute guy we saw by the hotdog stand saw you and recognized it?"

"Sorry to break your hearts, ladies, but I doubt any of the men we saw last week would even remember what we were wearing last Friday," I say, casting a wary eye over the men attracted to this particular hovel. Rad Tad, despite what his name insinuated, ran a bar that was neither rad, nor an actual bar. Of course, some of the patrons might disagree, but grudging from both their ranging levels of inebriation and the amount of cigarette smoke filming around near the ceiling they did not have much leverage with which to judge. Ten televisions, one bartender with a think handlebar moustache that called all the women "dahlin's," and a downstairs room with a karaoke box was not what I had pictured as a hopping Bostonian bar when I was growing up back in Indiana. Not that there weren't better places for 3 twentysomethings to waste time, but this had been the first place we'd been to that had actually not been completely jam-packed. So, instead of being adored by handsome men for our keen sports knowledge, we are in the corner casting wary glances at Stewaht and Bahb as they argue about Manny's next record and how many games out of first the Sox were. "In fact, I doubt any one of them would even remember what we looked like. We had too much vagina and too little testosterone for that group of rabid fans."

"Penny, you're one to talk," Julia says, setting down her half-empty bottle. "I remember a certain Daniel who sat three seats down from us that definitely would remember what you wore last week."

"What she means to say," Daphne interrupts," is that she remembers a certain naked Daniel whom she saw run out of your apartment the next morning wearing your father's old Sox jersey."

I shrug. "What? Just because I happened to get someone doesn't mean anyone there would remember us. Honestly, I doubt even Daniel would recognize me."

"Still won't return your phone calls?" Daphne asks, getting up to fetch another round. I shake my head, noting the familiar smudged vision creeping into my line of sight. Finally.

"No. And I really want that jersey back, too," I say, taking a final swig of my drink. I push back my chair, craning my neck to look through the misty smoke and see the short line of people at back of the room. Thank God. I hop down, feeling the uncomfortable crunch of fallen bar nuts on bargain shoes. "Damn, I gotta pee."

"And once again, Penny and Daphne leave their innocent friend Julia to the wolves," bemoans Julia, watching us as we both push in our chairs. I laugh.

"Don't worry, Jules," I say, grinning. "We won't leave you with Stewaht and Bahb too long."

"Besides, I think Harriet would approve," Daphne agrees, dropping her Kate Spade in her chair. "Find Mr. Right here, Julia. God knows I'm not going to be around very long. I want to see some grandkids coming from you soon."

"Fuck off," Julia smiles, and Daphne and I laugh before departing the table.


"Three more Heinekins," Daphne tells the barkeeper, who nods absently and continues to watch the last inning on television. She sighs, fully aware that she might have to pluck every single last hair from the man's face before getting his attention.

Daphne understood Boston's love for the Red Sox. A native Bostonian, Daphne had been in love with them too until bedding a rookie outfielder who called her Diana and left his jock straps on her shower curtain. That might not have mattered so much to Daphne, who adored everything with a Red Sox label, until said outfielder was demoted to the minors, and took with him her heart, her season tickets, and her father's 1912 Series foul ball. Impatiently, she drums her fingernails on the bar, an inaudible sound to anyone except herself. "Listen, buddy, the count is still going to be 2-2 after the commercial is over with!"

"I wouldn't even try it," the man next to her says. She looks over. He's about six inches taller than her, wearing the exact same jersey Daniel had stolen from me a week before. He motions to the other patrons sitting next to him. "We've all been waiting since Papelbon went in the 6th, so I highly doubt you'll be next in line."

"Really?" Daphne asks. She looks up and down the row of chubby, forty-something men slobbering over 9 men in tight white pantsuits being projected through a 2 foot box, and then looks down at herself, flipping her glance back up. "I disagree. I have two reasons why he'll get my beers before he will get your—"

"Jack. Jack Daniels." The man answers, the corners of his mouth turning up slightly. His worn Red Sox cap shadows his eyes so that Daphne can not tell if he is making fun of her, or if he is genuinely amused. Either way, she's receptive to the slightly toned dark arms that protrude from his worn jersey top, and even more so to the dark blue denim jeans he is also wearing. "It's 8:30. Are you already drunk enough to flash someone?"

"No," Daphne replies, craning her head to see if the bartender has changed positions. "But I'm willing to flash someone if it would help me to get drunk enough to be that drunk."

"In that case," Jack, Jack Daniels says, reaching into his back pocket, "Your next round's on me."


Julia hates when Daphne and I abandon her. We tell her over and over again that it is never intentional, that it just happens I finish my drink and need to pee at the same time. I blame it on my tiny bladder. Julia blames it on her mother.

"GOOD GAWD CALL IT FOR CHRISSAKES!" erupts from the next table over where 2 middle-aged men pound on the table and their half-full pitcher falls to the floor. It splatters Julia's shoes with amber-colored liquid. She wrinkles her nose, and grabs a napkin out of her purse, immediately trying to scrub the piss-smell out of her sister's borrowed heels. She should have known better, wearing them out with Daphne and I. We never had an evening that didn't end with one of us having a drink either spilled on us or stepping in someone else's wasted 3.50.

"Shit," she whispers, noticing how the suede has inhaled the beer as if it were oxygen. She'd have to dry-clean them. Did dry-cleaners even do shoes, she wonders, continuing to press the napkin fruitlessly against the shoe. There went another half a day's pay, and there was no doubt in her mind that her sister would never let her wear another shoe from her closet ever again. Julia had a wedding to attend in a month, and she'd have to go around her apartment building begging for another shoe swap, a task she was not looking forward to.

"Damn it, Rob!" one of the men at the beer-dropping table yells, noticing that his refreshment was not only empty, but gone completely. He turns around and sees Julia with her napkin pressed to shoe trying to mentally figure out who she had not borrowed from in three weeks and if they were even the same shoe size. "Hey lady!"

"Yeah?" Julia asks, looking up into the slightly tipsy eyes of a man 20 years her elder whose face she passed by every day before going into work. She gulps, and drops both her napkin and the shoe attached to it, then reaches up to adjust her top. "I mean, yes, Mr. Fisher?"

Greg Fisher owns Fisher's Public Relations, a multi-million dollar East Coast production that is looking to expand on the West Coast. This was Julia's dream job, right after marrying Prince William and becoming the first American Queen of England. Greg Fisher was divorced, and spent most of his day entertaining secretaries. Julia knows this because she works in the cubicle directly below his office, and hears every shriek, moan, and shout. Greg Fisher looks blankly at Julia, and for a horrible moment she thinks he recognizes her. For that fleeting moment, she wishes with all of her heart that her mother would show up, take her home, and knit turtlenecks for her to wear to work.


The line for the bathroom at the rear of the bar is not long, but neither is it nonexistent. One of the disadvantages to haunting smaller "taverns" such as these was the one-hole unisex restrooms, and the bathroom lines that imminently follow. I lean against the wall absently, then jerk back as my synapses scream in protest of the dirt and grime that probably now covers my bare shoulder.

"Disgusting," I whisper to myself, checking out my arm to make sure black blisters have not already erupted onto my skin. The walls are wooden and covered with enough local sports memorabilia to make any eBay customer cry with envy. Smoke clung to them like an ex-wife to alimony, desperate to leave its last mark on everyone who came into contact with it.

"You know, I hear the small pox is coming back into fashion," says a deep voice from behind me. I turn around, scrubbing the invisible germs off my hands and onto the floor. A tall, dark haired (and very attractive) man, looking very out of place in a three piece suit, is holding out a tiny bottle of antibacterial gel. "A squeeze?"

"Thanks," I say warily, opening up my palms. He obliges, and I rub my hands together, feeling the obligatory coolness as alcohol meets air. He nods his head, and then pockets the bottle. "Do you always go to sports bars and carry Germ-X with you, or did I happen to catch you on a good night?"

"I've found that in my experience, one can never be too careful in places such as these," he says, craning his neck to look at the head of the line.

"Your wife must love that," I say offhandedly. He erupts into laughter, and the woman in front of me turns around. "Will you stop? Everyone's looking!"

"I couldn't help it," he says, trying to sober quickly. "I've just never had someone ask that question—"

"It wasn't a question."

"Okay, say that remark four seconds into a conversation."

I shrug my head nonchalantly. "I don't see why my concern for a stranger's matrimonial status is so laughter-inducing."

"Clever." He says, stuffing his left hand into his jacket pocket and producing a small white box. He thumbs its top open and offers me a single stick.

"I don't smoke," I say, turning back around. To my immense relief the line is moving forward and I am only one person away. Daphne and Julia are probably already halfway done with their round, and are probably eyeing mine. At this rate, I just want to get back to my seat before last call.

"I'm not married," he taps me on the shoulder with the box, and as I turn back around, I watch him put the Marlboros back into his coat pocket.

"Why do you carry cigarettes around if you don't smoke?" I ask, crossing my arms. He shrugs, and leans against the wall.

"The same reason you ask—"


"Okay, the same reason you remark about my nonexistent wife." He's cute. Very cute.

"Sir, you're mistaking my general concern for something that it's not. I couldn't care less if you were married."

"Really?" He asks, dark eyebrows raised. "How noble of you. Tell me, what hours is the Goodwill store open for this week? I have a few suits I'd like to donate."

"Sarcasm will get you nowhere," I say, as the woman in front of me emerges from the restroom.

"Not even a phone number?" the man says as I open the door and step inside. In response, I close the door in his smiling face. Relieved to finally have some time to myself, I pull down my skirt and sit on the toilet, truly feeling the after effects of the three beers and single bottled water.

"You didn't answer my question."

"I'm using the bathroom!" I exclaim, squeezing my legs together. Through the tiny amount of light being produced by the flickering overhead lamp, I noticed with relief that the door was locked. "Can you not let me pee in peace?"

"Depends on what you're going to do when you get out of the restroom," he replies, and I can hear him smiling.

"If you let me pee…"

"I'll be waiting," he says, and I see the shadows of his shoes on the floor as they back away from the door.


Dear Trista,

First of all, welcome to Boston, the city that only sleeps from 4 am to 5 am because its mother tells it so. Don't worry, a young lass like yourself shouldn't have any problems meeting Boston's finest young'uns. A single Bostonian like you, I find that one can have the most fun lurking around many of the city's late night haunts, particularly on Red Sox game nights (that is, if you cannot afford tickets to the games themselves). These tiny, off the norm places hold many possibilities for excitement, one-night stands, and general tomfoolery. Just make sure, dear Trista, that your buoyant personalities stay in your Sox, and not out. Otherwise, we'll have a whole different column to write.

Loves, Penny


So, this is my new writing project this summer. Sort of in the same vein as AMOC (the dreaded "chick lit"), but very different. I hope you all enjoy it, and if you feel so moved as to review please, please give me constructive critism. One of the problems with AMOC, as many people told me, was that Carly was so unlikeable at first. I don't want Penny to be seen the same way, so let me know if you had any issues in this first chapter so I can revise before putting the second chapter up. I would look for a beta, but in my past experiance, all my "betas" did was spell check and not revise, when what I really needed was hard-core revision! Anyway, thanks for listening to me ramble and I hope you enjoy this story!