Loving The Lounge
A bar is too noisy and uncomfortable; restaurant disqualified for the reasons already discussed; your apartment, too forward (usually). That leaves the lounge, which is a brilliant invention in its own right. My friend Jeff and I have often mused about opening one in Boston, which is notoriously light on places to take a girl for a drink. Here are the requirements for a good lounge, of which there are many in NYC, several close to my
house:
- Enticing, dim lighting; no overhead lighting for our brothers who are getting thin up there.
- Comfortable couches that make the girl relax and allow you to be physical
- Nice, ambient music that is not too loud; a DJ is usually too much.
- Steady flow of cabs outside to fall into upon departure.
- Wait staff and bartender who get it and know your system.
Because this is the first time you’ll really engage the girl, the setting needs to be advantageous and play to all your strengths. Do not let her choose the spot; elements you can’t control will usually work against you getting laid. Make sure she comes alone. It’s also very important to have an understanding with the bartender and waitress, which usually means you tipping them well so that they follow your instructions to a “T”.
I don’t drink and haven’t done so for 10 years, but for all you booze-hounds out there, my advice is: take the night off. This brings me to an important rule of the game:
You should not drink while “on the job”.
Booze your tits off with your buddies on Saturday night, not here. Banging this chick is going to take your A-game and you don’t want to be dull. Until you establish yourself with the bartenders and get comfortable with your spot, you should show up a bit early, well-dressed (it doesn’t hurt to throw on a suit, at least not in NYC) and post up at the bar. Quiet nights are best, because they’re more intimate, and also because you’re more likely to find an open couch or nook in which to cuddle.
Tell the bartender how it is - she works for you for the 2 hours or so you’ll be there. I tell them I don’t drink but that I am meeting a lady, and that I don’t want her to feel uncomfortable so could they please bring me seltzer waters, in a high-ball glass, with a lime. And call it a Tom Collins. Or a Gin and Tonic if you prefer. Never leave your drink, and don’t let the girl sip it – she will freak out, I guarantee you. If you go to the bathroom, take it with you. When done, take both her glass and yours to the bar and give them to the bartender. Also, I find that drinking 2 or 3 seltzers on top of the meal I ate an hour before (solo or with a buddy) can be a challenge; I usually tell the bartender to make mine almost entirely ice; hers, little ice and stiff.
Bring the drinks back (it’s best to order at the bar while she’s sitting on the couch so she can’t hear the conversation) and do a nice little toast, making strong eye contact when the glasses clink. Avoid giving orders to the waitress out loud because she may hear you say “Tom Collins” and respond, “I thought you were drinking seltzer” or something worse.
Tell them to ask the waitress not to announce the drink - they often do: “Apple Martini for the Lady and a seltzer for the Gentleman”. You’ll be fucked if they do that – not the good way. Also, and I learned this the hard way, don’t let the girl see the bill. Sure drinking water keeps the cost down, but she’ll flip when she reads, “Seltzer - $4.00” after you’ve been drinking “G&T’s” all night.
I was able to avoid terrible embarrassment one night when precisely this happened by looking sheepishly at Nicky, and saying “Look at that – they undercharged us. Should I mention it?” She was still suspicious. Save yourself a huge problem - keep the bill private.
This is an obvious point, but I’ve had weird situations and my friend Nathan once met a girl, invited her to a drink and she brought a friend. Can you believe that shit? He rightfully refused to pay for their booze.
Also, it’s a statistical fact that it’s far harder to have sex with a girl when she’s in a group setting. Partly girls don’t want to disappear and hence be labeled a slut and partly they are having “fun” with others, making it nigh impossible to isolate a would-be candidate. Avoid at all costs; reschedule, if you must.

