Chris Brown shows chin-gash on Twitter

Despite the rumors that Chris Brown and Rihanna are back together (they have been partying next to each other an awful lot lately), the rapper is still technically dating Karrueche Tran. Meanwhile, Rihanna has been romantically linked to the most emo hip hop star of all time, Aubrey "Drake" Graham.

Eventually, we knew, this would turn ugly. We just didn't expect Chris Brown to be the one who walked away with the boo-boos.

According to the Daily Mail, Chris Brown and Drake danced a tango of pain last night at the downtown club W.i.P. While the previous evening Mr. Brown had hit up Greenhouse with his lady friend, last night he was apparently out with just his crew in the basement below the SoHo club. That's where he sent over a bottle of champagne to Drake's table. The bottle came back with a note, "I'm f****** the love of your life, deal with it."

Again, let us stress that this is what allegedly happened, because we really can't see Drake stepping up like that, especially with Mr. Brown's notorious temper.

Things got ugly between the two groups, and earlier today, Chris Brown's Instagram account had a picture of a nasty gash (shown above) along with the caption, "How u party wit rich n**** that hate? Lol... Throwing bottles like girls? #shameonya!"

This picture and the message have since been deleted. Perhaps Chris Brown doesn't want to admit that he got into a fight with Drake over Rihanna, or rethought the brilliance behind telling the world that Drake's crew managed to beat him up.

Either way, this will be the defining East Coast/West Coast feud of our hip hop generation...except, of course, that Drizzy is Canadian and Breezy is from Virginia.

La Pomme.

Thomas Monson, the founder of Bookabottle, met The Observer at midnight on a corner of Union Square in a black two-door BMW. He leaned a dress sneaker against the door, drumming his fingers on his knee and listened  to opera by the blue light of a third-party stereo system. This was actually very much in keeping with our expectations—on the website’s FAQ, the people behind the company site are described as “a group of Ivy League nerds that like to party.”

“I’m not a nightlife person,” Mr. Monson said as he pointed the car west through the rain. Next to him sat Seung Hee Kim, a very attractive woman in a short skirt and wellies. The FAQ phrase is more about the spirit in which the site was created, he said. “I don’t like going out. Like right now I really just want to go to sleep, and Friday for me is a crazy day because I literally do a 22-hour day on Friday, every single Friday.”

It was perhaps inevitable, in the Groupon era, that the frenzy for local discount sites would infect the nighclub bottle service business. Bookabottle works like this: Users select a day and a preferred environment ("upscale lounge" vs. "nightclub"), and Bookabottle allows them to pick from some 30 venues and a variety of liquors. Pre-booking means that bottles that usually cost around $350 can be had at a 20 percent discount. The purchaser then flashes his receipt at the bouncer, bypassing the line outside.

It’s a controversial concept. If you’ve ever had to watch a friend explain that you can actually save money with bottle service if you get enough people to go in on the bottle, you’ve experienced Bookabottle’s somewhat tragic contradiction first-hand. And quite possibly lost contact with that friend.

Mr. Monson is confident that there’s a large market for the customer who wants to make it rain responsibly, and at a designated time, and, more broadly, wants to change the very nature of going out. Mr. Monson is obsessive about customer service, and raises his voice only when he talks about the seedier elements of nightlife. At times he projects the air of a dorm’s RA, who, hey, guys, likes to have fun too, but just wants everybody to be safe while they’re at it.

At some point in the night, a customer service representative will swing by to check up on each customer. Ms. Kim usually handles this duty, Mr. Monson explained, because customers are around 80 percent male and would “much rather be greeted with a beautiful woman” when it comes to customer service. Ms. Kim stared out the window during the compliment, and after it.

“I stay up until about four just in case there are any issues,” he said. “[Ms. Kim] has my phone number, the mangers have my phone number, the customers have my phone number.” He demurred on the topic of what goes wrong at 4 a.m., referencing hypothetical mischarges. “For the most part things run very smoothly, but we’re still in this beta stage where I still haven’t gotten things perfect, and not to say that everything will ever be perfect, but we can do a lot better than what’s going on right now in nightlife.”

It’s hard to say what exactly appealed to Mr. Monson about the first stop of the evening, La Pomme on 26th, which seems like a fairly standard nightclub and shares the block with two barbeque restaurants and a place that teaches Israeli martial arts. Nostalgia perhaps—the room is purplish and glossy in the way things were on TV shows at the end of the ’90s.

“We booked the bottle service because one of our girls is engaged,” said Bookabottle user Reno, a tiny woman in a tight dress who falls in the just-under-30 age range. She waved at the group of friends dancing in place around their table. The shin-height table held their liter of Ketel One and chasers. “It’s a pretty good deal.”

“She’s taken, she’s taken!” one of the friends shouted, trying to wave the Observer away. Reno shot her a look.

“We don’t even do bottle service much, but we do party a lot and we were looking on-line, and we saw this stuff it was like, Ah, Bookabottle what’s that?” said Reno (her name comes from Indonesia, not the place where you shoot men just to watch them die). They’re regulars at R-Bar, but this was their first time at La Pomme. “We wanted to try this place out. We go all over the place, our girls do, and we party a lot.”

How frequently?

“Once a month,” she said, then considered. “In the summertime, we go out every weekend. Especially on rooftops, because it gets too hot.”

“Exactly!” her friend Helena agreed. She’d scooted around the miniature table because she heard someone discussing partying, or discounts. “I’m Yelper,” she said. “I do a lot of research, I try to save money. I’m Chinese, so I’m cheap, but I like to spoil myself.”

The conversation transitioned, seamlessly, to the women trying to convince the Observer to take a shot. Other members of the party, who’d been otherwise involved in bounce-dancing or chatter, fell into the chant almost reflexively.

“Shots, shots, shots, shots, shots,” they said. The Observer said and did nothing, and the chant died down.

The Observer piled back into the BMW with Mr. Monson and Philip Kennard, the site’s CTO and co-founder, who’d met us at La Pomme. Ms. Kim had been waiting in the back seat.

Mr. Monson used to be a business vice president at Hopstop—at his insistence, let’s just say he’s around 30—and, he explained, there are some things about nightlife that he doesn’t understand. He goes out of his way to pick the clubs with only the finest reputation and the most stellar customer service around, so who would want to go anywhere else? Conversely, what club could turn down the guaranteed market he’s offering when the mark-up is already so obscene on a $40 bottle of Grey Goose?

“If you know that you can sell your inventory, and you’re not making a 1500 percent markup but you’re still making a 1200 percent markup, common sense says do it,” Mr. Monson said, pounding the wheel with a palm on the last two words. He is, he explained, an “entrepreneur down to the bone.” This is not his only venture, but he clearly thinks it’s among his more promising ones. He says there have been several hack attempts on the site and his email, in an attempt to steal his business model. He’s lost 40 pounds developing it.

Ms. Kim also decided to wait in the car at R-Bar, just below Houston. R-Bar is supposed to be strip club-themed—there are enough oddly placed poles to wear out even the most space-creative ecdysiast—but with its red lighting and gold-framed paintings, the an overall effect of the place is “Haunted Mansion meets an erection.” The waitresses, and the manager, all wear red t-shirts.

We found the shaved-bald Bookabottle customer Sanjay not far past the entryway stripper poles. He gave his friend Anup’s shoulder a hearty slap.

“He just settled down a little,” Sanjay said. “But this man here was single-handedly supporting the New York nightlife industry for a while. He was far more notorious that I was.”

Both were a-bit-over-30. Anup looked left and right out of humility. “My doctor said I need to calm down!” he said.

“He also just got married recently,” Sanjay said. “That’s the big reason. And my girlfriend’s leaving me so I’m going to start going out more.”

He added, “It’s a mutual understanding. I’m just not the guy she wants to spend the rest of her life with.”

Their cramped table was only a few steps from the bar, making its convenience factor low, but they’d attracted a few friendly females, including another bride-to-be, this one in a veil, wearing a ring with a flashing plastic jewel. She said she wasn’t sure whose table this was.

The two work in finance (“Don’t mention that too loudly because we’re not a very popular bunch right now,” Anup said seriously. “We’re having fun but nobody’s asked me what I do for a living. As long as I get them drinks, things seem fine.”) They weren’t attracted to Bookabottle for the discount, then, but for its guaranteed entry.

“You know how it is with New York City nightlife,” Anup said. “You’d have to know the bouncer who would let you in and you’d have to sort it out with them. This way you don’t have to worry about the hassle because Bookabottle is at the club beforehand. If your bouncer’s on vacation or whatever you don’t need to worry about that shit.”

It's important to keep the glamour in perspective, Mr. Monson said repeatedly. “It’s so easy to get sucked into nightlife, if you’re working in that business.”

This was on an earlier phone call, where he’d dropped the RA act to adapt the tone of a burned-out rocker. “The second you forget the party is not yours is when things start to go wrong.” If he ever seemed tempted by the nightlife game himself it was at Cielo in the Meatpacking District, which has a great reputation in nightlife “the same way Goldman Sachs has a great reputation in finance,” he said.

After a businesslike frisking by the giant manager George, Mr. Monson and The Observer entered the club to stand at the back of the room as green lasers scanned just above head-level. The walls were some kind of gray leather upholstery, segmented like an airline seat, or a padded room. George sidled up and crossed his arms, indicating the DJ, someone famous to people who follow that kind of thing. There were no customers here. Mr. Monson just wanted The Observer to see the place.

“My goal is to go through life completely unnoticed and unspoken of,” the Cornell grad said later, growing philosophical as he drove The Observer to the A train around 2:30. “Ultimately I hope to end up somewhere completely isolated, maybe in Montana or something.”

At the subway, he asked that Ms. Kim step out of the car so that The Observer could see her wellies. They’re part of his latest venture Zoubaby.com, which offers a patented way to monogram rain boots.

Update 3:40 p.m. Corrected Mr. Kennard's title, and added his name.

Mr. Grossich: Well, it’s not so much snobbery. At the end of the day, I’m a marketing guy, and marketing is all about selling and finding a niche that you can own and cultivating that niche. … If you want to wear shorts and a ripped T-shirt and go have a drink somewhere, there are plenty of places you can go.

The Campbell Apartment’s dress code says: ‘Proper Attire Required. Absolutely No Athletic Shoes, T-Shirts, Sweatshirts, Baseball Caps, Shorts or Torn Jeans.’ Did you write that?

We started off with the simple ‘Proper Attire Required,’ but it was too open-ended. … I must say I appreciate your respect for our dress code, because there are journalists out there, who will remain unnamed, who have almost a vendetta against us because they were turned away at the door when they felt that because they were journalists that should somehow make a difference.

I assume you mean Times’ restaurant critic Frank Bruni, who wrote last year about being turned away from Campbell for wearing ‘a pair of very, very expensive Tod’s shoes’ that your doorman mistook for sneakers. Did you apologize to him afterward?

That wasn’t the person I had in mind, but certainly to start apologizing for our dress code starts to challenge why we have a dress code. Honestly, I can’t recall what we did, but we try to train our hostesses as best we possibly can, because it’s a very touchy subject. You walk in and, you know, I understand it, people take it very personally. It’s like—‘Max, I don’t think you’re worthy. Get the hell out of here!’

Your company describes its lounges as the city’s ‘most refreshingly civilized places.’ Isn’t poshness and civility out of vogue?

With all that’s going on in the world, and all the issues with people losing their fortunes or not being able to get a job or make any more money, it’s a relatively small expense to treat yourself to a plush environment, a well-made drink.

Does your World Bar in the Trump World Tower still have a $50 drink with drops of liquid gold?

Yes, we do.

Isn’t it a precarious time to be a king of the New York cocktail lounge—sort of like being a top Hummer salesman?

Overall, it’s a very sophisticated city that’s been at the center of this kind of lifestyle situation forever.

Lifestyle marketing seems dead: People aren’t buying something because it taps into what they want to be; they’re buying it because it’s a bargain or will really help.

It depends on what you’re selling! We’re selling ambiance, we’re not selling Chevrolets.

But isn’t the fancy, cigarette-holder, horn-rimmed era gone? The days of the big swinging dick, as Michael Lewis called the Alpha Male trader, were declared dead in September.

Goldman would argue differently, I think! That’s another story.

You opened New York’s first cigar lounge, the Cigar Bar, but now people can’t smoke in your places (except the Carnegie Club). You openly hated the ban when it was created, but what about now that it’s been awhile?

I still think it was somewhat arbitrary. We are living in a society that has particular freedoms. … The flip side for me is obviously I’ve saved an awful lot of money reupholstering.

You recently leased a former post office on the ground floor of the iconic Empire State Building for the Empire Room, which opens in the autumn. Its style harks back to the 1920s?

People, particularly in times when things are difficult, want to hang on to something. I think, universally, people continue to think that the past is somehow better than the future.

Eater.com made fun of the chandelier and dotted carpet: ‘It's like being on a third tier cruise line or maybe a Marriott Renaissance.’

Obviously, they’re not our customers, are they?

Your places have gobs of nostalgic, Old World glamour, but one thing they don’t have is youth. Are you envious of hip but gourmet downtown places like Death & Co or Milk & Honey?

Not really. We get those people, but it’s a different experience. We don’t shun youth, but we certainly have a franchise that I guess one could consider a little more—I don’t want to say adult—but a little more sophisticated in that respect. I’m sure we have plenty of customers that enjoy both.

Are you dismissive of the gourmet, organic cocktail movement?

I respect it, but there’s a point where, in my mind, it becomes almost too precious. If you’ve got 150 people and the bar is three-deep, there’s not a lot of time to make a drink with an eye-dropper.

Graydon Carter’s mural-covered Monkey Bar and Waverly Inn both want to be versions of the Chrysler Building’s vintage, gilded Cloud Club. Have you been?

I’ve been to Monkey, not to Waverly. … He’s had great success. Granted, you can’t overlook the fact that he’s the editor in chief of a very popular global magazine, and I’m sure that has something to do with it. But still.

You owned a modeling agency, among other things, before going into cocktail lounges. Do you miss it?

We had some success. It was called Punch Models, we were a boutique modeling agency just before boutique modeling became very in vogue. The thing I can say I’m most proud of is I didn’t lose my shirt. Didn’t get rich, didn’t lose my shirt.

Tishman Speyer basically evicted the Ciprianis from the Rainbow Room at Rockefeller Plaza earlier this year. Would you be interested in it?

We’ve been approached about it. … It would certainly be possible to take over the Rainbow bar, but to take over the food service? No.

You were reportedly sued for discrimination last year after hiring only women for hostess jobs. The Equal Rights Commission apparently fined you $15,000, but you appealed. How did it turn out?

It was ridiculous, frankly. As I understand it, what happened was, there was a gentleman who came in, we were interviewing for hostesses. There were other men there, he wasn’t the only man. It wasn’t that it was a man or a woman—we didn’t choose him! I really felt like we were set up a little bit, and I was really put off by all that. And if my memory serves—it’s been a while—I think we settled for far less than that.

You filed suit in State Supreme Court three years ago after the Parks Department replaced your Patio Café with the New York Milkshake Company in Dag Hammarskjold Plaza. What happened?

On the surface, we were simply outbid. … As the judge in our case continued to say to us when we were presenting our side of the argument, his refrain was, ‘Why would anyone want to do business with the City of New York?’ And perhaps he was right.

mabelson@observer.com