Best bar to close the deal

Brandy Library

This old world, upscale TriBeCa lounge is the perfect place to conduct a sultry evening filled with seductive glances and flavorful liquor. Stocked with the best Brandies and Whiskies, you will have a wide variety of options that will leave you feeling powerful and relaxed while old-Hollywood drinks, such as the French 75,  will be sure to make her feel like a starlet.  The low, smooth leather couches almost make it impossible to not lean towards your date while the warm, dim lighting, combined with the burning fireplace in the winter, make it almost impossible for her to resist whispering flirtatious temptations into your ear.  The food is good, although mostly unnecessary, as you will be too distracted by your date to think of eating. I recommend going on the weekends to avoid the business men during the week, although any night in this lounge is nearly flawless.  If you want to close the deal or just spice-up your existing relationship, get dressed and have drinks at Brandy Library.Brandy Library located at 25 N. Moore Street, near Varick Street

“everyone likes being complimented, even if they know it’s bullshit.” – my father

There is no sound sweeter to a woman (and maybe even a man for that matter) than a compliment.  We love it!  We love everything about it -even when we know you are feeding us lines. That’s because we want to believe it. I mean, who doesn’t want to believe great things about himself/herself?!  That being said, if you aren’t comfortable giving a compliment, it will often come out forced or sounding like a sales pitch.  In addition,  women will often get a bit uncomfortable when they are complimented because they don’t know how to respond.  Below are some helpful tips on how to give a compliment that will leave her smiling and wanting more…of you!

Delivery: how to sound natural and genuine

The goal when giving a compliment is not sound like you do it all the time to every woman that walks by, but to also not sound forced and awkward like you don’t know how to talk to women and needed to rehearse the compliment.  Either of these deliveries puts a woman on edge and forces her to response.  The best type of compliment leaves little time for a response, other than a quick thank you.  If you aren’t used to complimenting women, start by practicing on a female coworker.  One day simply say to her “I like your shirt” or “your hair looks nice” in passing.  Say it matter-of-factly, as if you are telling her it is sunny outside then keep walking or quickly move on to another topic without skipping a beat. It doesn’t matter if the only female you work with is 60 years-old and scary, this practice will get you comfortable with having that type of interaction with women.

What to compliment:

Stick to the basics.  Hair, clothes, jewelry or shoes.  All of these items are in the safe zone…they are things that won’t trigger a bad reaction and women hold a lot of pride in each of them. You might feel weird complimenting something she is wearing, but believe me, she’ll love it.  About 5 years ago a bouncer complimented my shoes as I was walking into the bar and I still clearly remember him and the shoes. The exchange was all of a 3 seconds, but it made me feel good!

When to compliment:

  • The most important time to compliment a woman, and also the most natural, is when you first see her.  This does not apply to women you are approaching in a bar, this is only for women you already know.  For example, if you are meeting her at a restaurant for dinner, when she walks in and greets you simply say hello, hug/kiss her and when she pulls away from the hug say “you look nice” or any variation of nice.
  • When she is dressed up.  If she is ever dressed up more than normal it is imperative that you tell her she looks great.  “Wow, you look unbelievable/great/fantastic/beautiful.”
  • During sex. this can be a really intimate compliment, such as looking her in the eyes and saying “you’re so beautiful” or something a bit less meaningful, such as “wow, you’re sexy” while looking at any part of her other than her eyes.
  • Do not try to use a compliment as an introduction.  If you have never met a woman before and are approaching her in a bar, do not think that complimenting her will get your foot in the door.  In fact, it will ruin your chances by sounding cheesy.

Now go make her feel special and compliment her.

Boxers or Briefs

I went out with a guy about a year ago, who was a bit older and more established than me.  To paint the picture, he owned a $2 million apartment on the UES (no not the UES-er) and wore a $10,000 watch, while I was living in a two bedroom apartment with a roommate.  I didn’t date him for the money, but all of this is imperative to understanding how the events of our short-lived relationship unfolded. So we went out a few times and each time I had a lot of fun. For our third date he invited me to a nice dinner on a Saturday night.  Up until this point we hadn’t had any sleepovers and our two previous dates were during the week, meaning I was wearing conservative, work attire.  I was really looking forward to finally having a date in which work clothes and a cab ride home at the end of the night were not part of the equation.  For the evening I planned on wearing a strapless dress so I decided to get some sexy strapless lingerie to go underneath.  The date couldn’t have gone better, and by the end of the night we could barely keep our hands off of each other – I was dying for him to take me home.  When we got back to his apartment and started hooking up he couldn’t find the zipper on my dress so I unzipped it feeling sexy and excited to reveal the black lace corset I was wearing underneath.  To my surprise, when he saw my lingerie he said “why do you have so many layers on?”rather than  “wow that’s hot” and jumping on me like I would expect any warm-blooded male to do. I was speechless and mortified…and totally turned off.  I just wanted to put my dress back on and slink away I was so embarrassed, but I refused to be that girl, so I ignored his comment and continued on with where we left off.  Within seconds his pants came off and there in the front of his boxers was a huge hole. No joke, probably  3 inches long over his right thigh.  I was disgusted! Here I am in $200 lingerie (which he had the nerve to negatively comment on) in his $2 million apartment and he couldn’t buy a new pair of $5 boxers. Was he serious!? This is a 43 year old man- why did he not have fresh, clean (yes, I am assuming they are dirty if they are ripped) underwear?! After seeing that I did not want to touch him and got stiff and awkward. Let’s just say the night did not end to his benefit. My point, gentlemen, is that women really care about under garments for both you and themselves.  We really don’t care if you wear boxers or boxer briefs (tighty whiteys are never a turn on, but I have seen some black and grey briefs that were hot – although I wouldn’t encourage wearing them the first time you are going to be with a woman), but whatever you are wearing should be clean and in tact. I mean, if you are that close to getting laid, why would you mess it up by not having normal underwear?! And I can assure you that women put a lot of thought into their bras and panties, so take a moment to acknowledge how good she looks in them- just simply say “wow” when you see her in them.  Believe me, it will go a long way!!!

If you are looking for a good pair of boxers or boxer briefs, see my recommendations below. General rules to follow when buying underwear is to stay within the blue family for boxers and for boxer briefs stick to grey or black.

What your profile picture says about you

I once forwarded my friend a picture of a guy from, who had reached out to me.  I was excited about this guy and wrote “I’m excited- a hot, normal guy.”  His profile picture was of him on a boat wearing a T-shirt, hat and sunglasses.  My friend simply wrote back:

“Hat = bald

Sunglasses = wrinkled

Chest up  = short

Let’s not jump to conclusions….”

Yes, sadly this is how many (not all) women think.  I never ended up meeting this guy, but based on his other pictures I would be willing to bet good money that he was neither short, wrinkled or bald.  That being said, it doesn’t matter, since it’s all about perception.  On any online dating site, your picture is the most important aspect of your profile. Both women and men see a person’s profile and immediately create an image of who they think that person is.  If I don’t like what I see in the profile picture I am never going to take the time to read the profile.  Therefore, here are some simple guidelines to creating the image you want, whatever that may be:

1. Under no circumstance should you take a picture of yourself in a mirror with your camera phone.  Are you so anti-social that you don’t have a single picture of yourself with family or friends or standing in front of some famous landmark!? It comes off as trashy or lame. Just don’t do it.

2. Don’t post a muscle picture of yourself at the beach, in a bathroom mirror (see above), or anywhere else.    Unlike men, I have never once heard of a woman going to an online dating site to get laid.  If she is even halfway attractive she can simply go to a bar on any given night and find someone.  Therefore, seeing your perfectly chiseled body is only going to either A) make her think you only are in it for sex and lose interest or B) intimidate her.  The only time I have ever seen a body picture be acceptable is when the guy is in the pool/water with either a bunch of friends playing around or playing with a kid (usually a niece or nephew) and the focus isn’t on his body, it’s on his activity.

3.  You must include pictures with friends.  In The Departed Alec Baldwin’s character says “Marriage is an important part of getting ahead: … people see the ring, they think at least somebody can stand the son of a bitch…”.  Well for that same reason, you need to include pictures with friends, or at lease pictures in which it is clear that you cropped friends out.  If you don’t have a single picture with a friend, women assume you have no friends and therefore must be a socially inept shut-in or a weirdo.

4. If you are posting pictures with women other than family members make sure the women are hot, but classy.  Any woman in your pictures should look like the type of women you want to date.  Women are extremely territorial so the best thing you can do is include pictures with other woman to spark their competitive nature and prove that you are appealing to other women (even if it is just a friend or even your friend’s girlfriend). Be warned, this is a tricky tactic that can easily backfire.  If the woman is too hot, it is intimidating, but if she is too plain looking we think “he must not be that great, I can do better.” (although I would say it is safer to go with a plain Jane than a super gorgeous woman). One guy I was initially interested in had pictures of himself from what looked like a club in Vegas with two women with fake boobs, wearing close to nothing and he had a shit-eating grin on his face.  As soon as I saw that picture I thought “gross, what a creepster!”  I get that pictures like that might give you huge bragging rights when shared with your guy friends, but they will never appeal to women. Honestly, if he thought that made him look good I shudder to think how he would be in real life.

5. Never try to make a sexy face! Men, your sexiness lies in your manliness, and there is NOTHING manly about you trying to look sexy. According to OK Trends the most effective pictures are those taken in which you are not smiling, although smiling doesn’t hurt and I have to say, personally there is nothing better than a good smile.  Also, it doesn’t matter if your profile picture is a clear picture of your face versus a full-body shot. Therefore find whatever your best asset is and make sure it is the focus of your picture.  Like i said, it is all about perception.  The profile picture just has to be good enough that it makes her consider you.

6. Be aware of the clothes you are wearing in your pictures.  Although your pictures might be taken on a random day when you happened to just throw any old shirt on, a woman will look at that and think that is reflective of your style.  Be sure your clothes reflect the style you would want in a woman.  For example, if you want a classic, preppy woman, you should be wearing classic, preppy clothes whereas if you want an edgy, artistic woman you should be wearing something with an edgier style.

How to write your online profile

Let’s face it, in today’s world it is almost ridiculous to talk about dating without talking about online dating.  The large majority of people I know, both male and female, are, or have been at some point, on an online dating service.  The difficulty with online dating is that people are much pickier than they would be in person.  I think of some of the men I’ve dated who I originally met at a bar or through friends and realistically,  if I saw their profile online I probably would have never been interested. They wouldn’t be good looking enough or tall enough for my online criteria- or their personalities that hooked me wouldn’t translate into a written self-decription.  That being said, they were great and I had so much fun dating them.   That’s why it is so imperative to have your profile really reflect the best version of yourself, and the best pictures (refer to What your profile picture says about you) so that you can get to the first date stage.  Think about how much women analyze every little (dating) situation- so just imagine how much we analyze your profile!

The key with writing a good profile is to stick to the basics and don’t be offensive.  Look, she is basing 75% of her decision on how you look.  So if after seeing your picture she still wants to read your profile, then all you have to do is not mess it up.  Yes, that’s great if you are witty and can put a funny story in there, but I have found that most of the men who have really funny, great profiles are usually a disappointment in person.  Bottom line: It’s OK if your profile is the same as every other guy- stating that you are laid-back, loyal, honest, family-oriented and love to travel (and yes, nearly every single profile I have read says those things).   No girl is going to find anything offensive about any of those things…well, assuming you say it in a normal, nice way.  An example of the wrong way to do it is the profile below.  The is a real profile, no joke!

His stats: 38, classically handsome, full head of brown hair, 5’10”.  Based on his picture, a catch. Then he felt the need to write this:

“I’m living like there is no tomorrow, because there isn’t one.

Happiness is freedom from fear. Leave yours behind and surrender to your senses.

I’m no stranger to beauty.


-Heart Breaker
-Race-car Driver
-SoHo & Scarsdale
-Wall St.
-Ivy League
-Deep voice
-Smell great
-Stiff stubble
-Sexy after dark

I’m handsome, dark, tough and mysterious.

Spring Travel:

Feb: Paris

March: Rio

May: Cap d’Antibes

May: Monaco Grand Prix


Miles Davis
Bruno Mars
B Tribe

Ps, if ur alarm clock is going off, I’m not in bed.”

Is that a fu*king joke? Honestly, any woman with an ounce of class and intelligence would think he sounds like an insecure d-bag. The only woman who would ever be attracted to a man who said this would be a trashy, gold digger. Now is that really who you are trying to meet? If so, follow the template above.  If not, then follow the simple rules below.

1. Don’t refer to your looks unless it is in a self-deprecating, funny way.  If you want to say that you look good in a suit, then post a picture of yourself in a suit- never write it in your profile.  Believe me, we can decide for ourselves if we find you attractive.  By mentioning it you will only sound superficial and self-obsessed or insecure.

2. don’t include cliche quotes or sayings, such as “living like there is no tomorrow.” Really, how many people really live like that?! And even if you are one of the .0001% of people that does, you should be smart enough to think of a more original way to say it.  Using cliche sayings makes you sound like a used car salesman – like you are trying to be smooth, but aren’t cool enough to pull it off. No woman will ever be turned on by that.

3. Don’t refer to sex! Yes, we get that sex is a huge part of dating, but we want to believe that the men online actually want to DATE us, not just sleep with us.  Therefore, even if you are online just to get laid, don’t ever admit it to a woman or make it obvious.

4. Use proper grammar! I get that not everybody is the best writer, especially when it comes to having to write about themselves- it’s nerve-wracking.  That being said, poor grammar, makes you look unintelligent or like a foreigner very quickly.  Have someone proof read your profile if needed, which leads to my last point…

5. always have a woman, whether it be your mother, sister, friend, or friend’s girlfriend read your profile prior to posting it.  I guarantee she will have a few pointers that will make you sound more appealing to the opposite sex.

If you need me to proof your profile, send a draft to  I will not post your profile draft unless you allow me to do so.


One of the most perfect go-to dates for any stage of a relationship, and definitely my vote for the best first date, is going to a wine bar. Living in NYC, it’s almost guaranteed that your date will be a wine drinker, or at the very least will have an appreciation for wine. In addition, wine bars typically have the perfect lighting to set the mood, along with an air of sophistication and a sound level in which you aren’t forced to yell to hear each other nor are you forced to whisper to avoid being heard by nearby patrons.  A great new wine bar to enter the scene is Corkbuzz, located just south of Union Square at 13 East 13th Street. Competing with the likes of nearby Pippa and Tarallucci E Vino, Corkbuzz has shown that perhaps those other spots are no competition at all. The bar is perfectly decorated to create a feel that is simultaneously modern and comfy and is more spacious than the typical wine bar, with all seating, including the stools at the bar, being regulated by the hostess.  The food menu is more extensive than the typical cheese-plate-only wine bar menu, and served in portions that won’t leave you famished, but that she will actually eat in front of you. The menu will also save you from having to order several appetizers or tapas that add up to a large bill at the end of the night.  The wine list is comprised of wines that you most likely have never heard of, unless you are a true wine connoisseur, which takes the pressure off of you to pick a good bottle and puts all the work in the hands of the Sommelier, who is both knowledgable and down-to-earth.  Simply have your date describe the tastes she likes and your price point and you will be sure to get a great bottle.  In order to avoid a long wait for a seat, I would recommend going on a Tuesday.   They also offer wine classes, for those who want to brush up on their wine knowledge.

A bottle of the Ascheri Pelaverga Verduno ’10 with the braised short ribs, the mushroom pappardelle and the sauteed brussels sprouts to share

Watch to wear

Whenever I meet a guy I immediately check out his watch and his shoes- both are very reflective of the person’s personal style.  And let me tell you, most women do the same (if not both, then one of the two).  Bottom line: your watch and shoes matter.  One watch that I love that is currently on the market is the Mougin & Piquard for J.Crew Grande Seconde watch available in cream (pictured right) and black.  I typically prefer watches with metal bands, as leather bands seem a bit old, but this watch is classic and sexy and looks much more expensive than it’s $425 retail price.  This is a great summer or year-round watch that makes the statement that you are accomplished, confident and someone I need to know.

To buy the watch, visit J.Crew


UES-er from Westchester (provided to help you understand how women interpret dating situations)


Date: Upper East Sider from Westchester, age 39, HOT!

What: blind date from recap sent to my girl friends.  To make it more fun, I used the points system…

So I was ridiculously nervous – actually I don’t know if nervous is accurate, but I was completely dreading the date. I honestly couldn’t think of a single thing we would talk about and I felt like I didn’t have it in me to put my game-face on. The whole thing just seemed exhausting. Of course I got shitfaced (off of 3 glasses of wine! Wtf!), which I NEVER do on a date. But overall it was a good date and I left the date really wanting to go out with him again. I don’t think he’s the “One”, but I definitely enjoyed his company.

Things he did that got him closer to sexy time:
1. 10 points for being good looking. Pretty classic looking except he has a very crooked nose and space between his 2 front teeth that actually makes him cute and takes away from the d-bag overly-classically-handsome look. But is still very attractive. Immediately upon seeing him I was attracted to him- so my type!!

2. 6 points for wearing a pink tie. I LOVE when a manly man rocks pink (shirt or tie). It makes me think they are secure in their manhood (and have the goods to back it). And it’s a little waspy, which I love.

3. 10 points Although he wasn’t wearing cufflinks, which I typically love, but he had his initials embroidered on his cuffs. He wore a suit well. (refer to how to wear a suit)

4. 40 points for picking a good wine bar and having comfortable seats at the bar. Then (and this is really what the points are for), when this guy standing behind me at the bar started crowding me UES-er moved back and just pulled my stool towards him and commented on how the guy was rude for crowding me. You all know I love that on so many levels from attention to etiquette to proving he can effortlessly move a stool with my complete dead body weight on it…because you know that means he can lift me. 😉 just saying…

5.  5 points for being adorable and wanting to hold my hand, but being too awkward to really do it at first. At some point I must have been talking with my hands or something and we touched hands and he grabbed a few of my fingers (not the whole hand) and wouldn’t fully wrap his hand around mine. So instead he kept his fingers straight and just kind of squeezed my fingers between his fingers and thumb. It was adorable in an awkward kind of way.

6. 100 points for kissing me like a man and doing it well. He knew how to kiss! And he even went in for the kiss in a perfectly manly, aggressive-but-sweet kind of way. Then we continued walking to the next bar.

7. 10 points for ordering a chocolate dessert because I had mentioned liking the chocolate cake at Mezzogiorno. So he assumed I really like chocolate cake (which I actually don’t, but didn’t have the heart to tell him.) It means he was listening and I love that!

8. 20 points insisting that we go get food when I said I was hungry when I was willing to blow it off. And I like the fact that we just went to a bar with food and he didn’t try to go over the top and go to a restaurant at 10:30 at night. He simply picked the closest place that was acceptable. I was already interested, so he didn’t have to impress me with his selection.

9. 100 points for paying attention, but not referencing match or how we met. He made mention of a few of the things I had said in emails, but never once mentioned match or said “so you said…” while referencing my profile. It’s awkward enough, there is no need to bring it up on a date in public.

10. 20 points for admitting he googled me prior to the date. Yes, this would creep me out if I wasn’t interested, but I was.

11. 100 points because I felt like a WOMAN. I felt sexy and playful and womanly with him- exactly the way I want to feel with any guy.

12. 10 points because I was thinking about how there were a few awkward lulls, but we were together for over 4 hours talking. The fact that I could talk to him for that long is pretty amazing.

13. 300 points because he put me in my place by calling me out in the most perfect (and funny) way possible. Love when a man does that!!!!!! Might be my favorite thing!

14. 5 points because although he invited me back to his apartment it was indirect and said in a way that it seemed like an afterthought. Like he thought he had to say it, but never actually expected me to say yes. The date was sexy, but sex was never expected.

15. 5 points. He played minor league hockey for a year after college, which I normally would find incredibly sexy, but hockey players are not my type. He played lacrosse too, which is more my type.  That being said, I know he has a sick body and keeps it in shape.

Things he did to kill the sexy:

1. Minus 15 points for saying some inappropriate weird comments. Only 15 because they weren’t mean and seemed to come from a place of not knowing what to say and being nervous. He seems like a guys’ guy and seems like he could be a little awkward with women.

2. Minus 200 points for reminding me of my ex. Had the same mannerisms and talked in the same way. Almost seemed braggy, but I think (and really hope) it was because it was a first blind date.

3. Minus 10 points for saying he doesn’t like the Hamptons. He said it is too much of a scene and his friends always want to go to clubs there and he said it is easier to go to Westchester to just hang by the pool.   So although I don’t like his statement, I like the reasoning. Oh and he said he’s not a beach person, so I guess it should only be minus 5 points, because I love when people admit that.

4. Minus 1 point for having a really loud laugh. It kind of caught me off guard and scared me at first. Hahah.

The importance of a well-fitted suit

Men, you don’t seem to understand what a man in a well-fitted suit does to us women.  You know how you feel when you see a beautiful woman in perfectly tight white pants or a dress that is cut just low enough to show off a little more than the curve of her breasts? Yea, you know.  Well that is how women feel when they see a man in a well-fitted, nice suit. Now I’m not talking about only high-end, Armani-level suits.  The key isn’t the name brand or quality of the fabric- although both are nice and don’t hurt – the key is how it is tailored to fit your body. And no, you don’t have to have a gym-5-days-per-week body to pull off a tailor-fitted suit. That is the beauty of a suit, if it is tailored correctly it makes you look like you have a better, stronger, taller body than you actually have.  American men tend to shy away from having clothing be too fitted or tight, but I’m telling you, it will help your cause! I always joke that you can tell a man’s age by how his suit fits (at least in NYC).  The guys in their early to mid 20’s wear suits that aren’t tailored nearly enough (or at all), and the suit is always too big and ill fitting.  Most likely their mothers bought it for them for their college graduation and their fathers never explained to them that they needed to then go get it tailored.  Men in their late 20’s then realize they need to have their suits tailored, but are afraid to wear them too “tight” so the suits are still slightly too loose.  Then men in their 30’s seem to realize (or should) the importance of a well-fitted suit; they realize by wearing a suit you are demonstrating that you’re a MAN and all that implies – power, money, sex.  It turns us women on- a lot! Now this applies to all forms of a suit. My friends and I will always say how sexy it is when we see a man in a bar whose wearing suit pants and a shirt with rolled-up sleeves and no tie.  We know you were wearing a suit earlier that day and are winding down.  Believe me, any woman with any taste, loves a man with a nice suit.  Now I know suits costs a lot, even for non-designer brands, but in NYC there are plenty of places that offer great deals.  A great place to buy a suit at a reasonable price is My Suit.  You can get custom-made suits here, tailored to your measurements for around $500.  For those who can afford a higher-end make and brand, go to Mr. Porter.  So go, buy a suit and get it tailored to fit you perfectly!

Pictures coming soon…