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…

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No, I’m not going to offer to pay…

and you shouldn’t expect me to.  We are on a fu*king date and you’re the man.

I know, you think I’m a bitch for saying that, but I’ll start by saying the confusion in dating and total lack of rules isn’t totally men’s fault.  Nobody (men and women alike) knows what the rules are anymore and therefore are left unsure of what they are supposed to do; trying their hardest to not step out of line or do something that could ruin their chances.  It’s like walking on eggshells when you first start dating someone- fearing that any comment or gesture could be misconstrued.  And women have set the bar so low- so of course you aren’t going to do more if you don’t have to.  But does being with someone who has no standards really make you feel good about yourself?! Now don’t get me wrong, the women’s liberation movement was a great thing and I am thankful for it, but with that, women started taking on new roles in all areas of life, including dating, and not all of them were completely favorable for women or men.  Bottom line, in dating, men want to feel manly and in charge, like the protector/provider, and women want to feel like ladies, they want to feel pursued, and people want to know what the expectations are.  The man paying for the date allows both parties to play their respective ideal roles.  And let’s face it, when she does “the reach” she doesn’t actually intend to pay and is only doing it out of obligation so you don’t think she is ungrateful. I mean, can’t she just say “thank you”? Below are some guidelines you should follow regarding paying on a date.

  • You should without question pay for the first three dates.  After that she can start paying for a few things here and there, but for the most part, you should assume that you are paying for everything.  Yes, it sucks and it’s expensive, but it’s an investment and you shouldn’t plan dates that are beyond your budget. Once you are in a relationship, discussions can be had and that balance might need to shift, but in dating you should pay.
  • When she offers to pay it is just to show her gratitude, so simply tell her no as soon as she starts to do “the reach.” It’s even better if you can get your credit card out before the check even comes and immediately hand it to the waiter when he brings the check- it will avoid the awkwardness all together.
  • If she insists on paying for dinner/the date, dump her immediately.  I know this sounds harsh, but by insisting to pay she is taking the upper-hand in the relationship and is revealing her controlling, dominant ways.  Either that, or she doesn’t think you can afford it.  Either way, it is a bad dynamic.
  • Never split the bill.  You are dating, you aren’t friends.
  • I said this in the first point, but I really mean it, don’t feel like you have to have one expensive date after an other.  Believe me, if she likes you even a little she won’t care.  I would recommend you planning to spend the most on date #2 or 3, but don’t look to spend a lot on a first date.

Text me!!! How and When to Follow-up

Let me tell you, the 3 day rule is bullshit.  By the time the third day has rolled around we have already loved you, longed for you,  fought with you and gotten over you in our heads.  Yes, it is psycho, but every single woman does it. Every. Single. One.  After any good date we are on cloud nine imagining the possibility of you being the One, or simply someone who will temporarily amuse us and make us feel special for a little while.  Now granted, we don’t really like you since we still don’t really know you, but we are attracted to the attention and who we imagine you to be based on those few hours spent together. After a day or two the excitement slowly starts to wear off and we start to check our phones a bit more frequently, “When am I going to hear from him?” By day 3 we are going over everything that was said (and wasn’t said) on the date to explain why we haven’t heard from you yet. And by the end of day 3 we are annoyed and start to write you off.  Below is a play-by-play of how and when to follow up after a first, second and third date.

On the first date: If you really like a girl, ask her out again at the end of the first date.  Women are planners and we just want to know when it is we will see you again.  Be specific and agree upon a day to see each other next. Simply ask “When can I see you again?” and don’t settle for a vague response.  Don’t worry, she is never going to reject you to your face.  If she really isn’t into you, she will cancel over text, but if she had a decent time, she will most likely give you a second date simply because you asked.

30 minutes after the date: This is the most important follow up and yet the most overlooked. Text her once you get home from the date telling her you had fun and making sure she got home safely.  This will reassure her that you want to see her again and that you are a gentleman.

***the next morning: This is not a necessary follow-up and I do not recommend doing it often, but if you really like a woman, follow up the next day with a text stating “I made a reservation for X restaurant for 8pm on [agreed upon day].  Does that work for you?” She will be blown away that you took the initiative and will make her feel special.

A few days after your first date: depending on when your first date was this will either be at the end of the week (your first date was Tuesday) or Sunday evening (your first date was Thursday).  Simply text her asking how the rest of her week/weekend was.  This can create a little bit of a back and forth asking what she did and telling her what you did or have planned for the weekend.  Telling her parts of your schedule is a good way to create a closeness and make her feel secure (in other words, if you’re telling her what you did all week she is assuming you didn’t do it with another woman).

A day before the second date: text her to confirm your plans for the following night and tell her where you are going.  Women like to know in advance what the plan is so they have time to plan their outfit, etc. Believe me, we put in a lot of thought and prep work into every date, and that takes time.

Second date: Once again, if you are really into a girl, you should ask her out for a third date on the second date.  This doesn’t need to happen every date, but the key is to get to the third date because at that point it turns from you being the guy she went on that date with to a guy she is dating.  Therefore, lock down the third date at the end of the second date.  If you can, make the third date less than a week after the second.

Two days later: After the second date you should be texting every other day and should reference what you talked about on the dates.  Most likely she mentioned plans she had, or a movie she liked or even something you mentioned that you can reference.  For example, I went out with a man who talked about how he liked running in the park at night because it was too crowded during the day.  So a few days later, during the day, he texted a picture of the crowd running during the day followed by the text “see what I mean about the crowd.”  It was thoughtful and made me feel like I was sharing the experience with him.  In general, picture texts (of places or experiences, not yourself) are always meaningful and makes the text conversation more intimate.  On the flip-side, the follow-up text could be as simple as “how was dinner at X restaurant?” referencing plans she talked about having.

After date 3: Now after date three you really switch from going on dates to dating.  Most people are too busy to spend three dates with someone they are not truly interested in. After date three you should establish your communication pattern.  At this point a phone call can really seal the deal, but it could also sound forced and awkward.  It should be whatever you are most comfortable with, but it should be often- think daily- and should change from a keeping-in-touch approach to a more intimate, chit-chatty vibe.  For example, share stories about something that happened at work, or with your friends, and definitely share more about your schedule and what you are doing on a daily basis.

After having sex:  After a woman sleeps with a man she begins to panic a little. She thinks “Shoot, I hope he still likes me”, “I hope that changed things for the better, not worse”, “I hope he really wants to date me and wasn’t just interested in sex” or some variation.  Regardless of when you have sex with her, whether it be date 1 or date 10, you need to IMMEDIATELY plan the next date.  That means, before you let her leave your apartment, you schedule the date.  If it happens that you forget, then you need to follow-up with a text that same day.  So for example, say she slept over on a Friday night and left your apartment at 11am the following Saturday, at 4pm you should text her referencing something you spoke about and then say, “so what does the rest of your week look like?” Once she tells you, lock down a date…and if for some reason your schedules don’t workout, tell her that.  Simply say “ok, I’m not free those days, but I want to see you again, so next week?” You have no idea how much that will be appreciated! You must send a text the same day the sleepover ended!

Obviously, your communication depends on her participation and can vary greatly.  That being said, the above guideline is the minimum you should be reaching out to her – it also will make it easy for you and will keep her thinking about you in a positive way.

Overheard while out to eat (at a nice restaurant)

While out to dinner, there were two men sitting at the table next to us who appeared to be father and son. They were well-dressed and approximately 80 and 60 years of age, respectively. The older gentleman said straight-faced “he discovered he had crabs in his eyebrows.” Now I’m not sure how one gets crabs in such a location, but I’m thinking that whatever it was left him with a fishy taste in his mouth. Ha

Yes, she’s crazy

I believe every woman is crazy at least once in her life, usually with a certain man, but there are other woman who are just truly CRAZY. The woman below is batshit crazy.  My guy friend met her online and asked her to meet up for drinks to which she said yes and gave him her phone number.  This was the text conversation taken from his phone.


Kevin: Hi Sarah, it’s Kevin (names changed for purposes of this post). glad to hear Thursday works for you.  Is there a specific area you would like to meet? What type of bars do you like?

Sarah: on the UWS near 70th and Columbus.  Someplace like Bin 71.

Kevin: Ok, well then why don’t we just meet at Bin 71.  8pm?

Sarah: No, I didn’t mean we should actually go to Bin.  Just someplace like it.  (mind you the address she gave is 1 block from where Bin is located)

Kevin: um ok, well I don’t really know the UWS so I’ll look some places up.

a few hours later:

Sarah: Hey, really sorry, but I totally forgot I already had plans Thursday, so I have to postpone.

Kevin: No worries.  Next week then

Sarah: Ok thanks.


Sarah: Hey, my plans actually fell through for tomorrow night so let’s still meet up.

Kevin: Hey, sorry, I already made other plans since you said you couldn’t meet.  Let’s meet next week

Sarah: well I have dates every night next week, so I can’t. (Who says that!!!!)

Kevin: Ok, well then I guess the following week.


Sarah: So what’s the plan for tonight?

Kevin: ??

Sarah: I figured you would want to meet tonight since I am busy all next week

Kevin: No sorry, I told you I have plans.

Sunday morning:

Sarah: I met someone last night and he is great and I didn’t have to go through Match to meet him. so I won’t be going out with you now.  (does she really think a one-night stand will turn into a relationship!)

Kevin: Congrats.  Best of luck to you.

One week later:

Sarah: Want to grab a drink?

No response.


“I ain’t sayin’ she’s a gold digger, but she ain’t messin’ with no broke…”

This past August I went to my first Yankees’ game (and first professional baseball game ever) and it was great. My friend  knew a guy who worked for the team so we were given tickets to the Audi Club and inside the club we ran into an old friend of hers that was married.  As is typical whenever a married person is talking to a single person, the friend (we’ll call him Chris for purposes of this article) was dying to be entertained with stories of being single and our dating escapades. Throughout our conversation, Chris  kept mentioning “rich, successful, good-looking guys” that he either knew, wished he knew or wanted to set us up with.  It struck me that he kept saying the words “rich” or “successful” so I finally asked him why he kept emphasizing that the men had to be rich.  (Now let me be clear. Yes, a rich man would be ideal and that is one of the adjectives I would use when describing my dream man to a friend or family member, but I would never so openly talk about it with someone I just met.) He looked at me confused and then simply said “Well why wouldn’t you want a rich guy? That’s like a guy saying he doesn’t want a hot girl. It’s just ridiculous.” Yes, yes it is.  

Of course I want a rich man, and so does every other woman on the face of this planet!!!!!!!! That doesn’t mean I won’t date a man who isn’t rich, but it means I’m going to look for a man who appears to be financially comfortable and more importantly, ambitious and seemingly capable of becoming wealthy. Like with everything, though, it’s all about perception. Below are some indicators that women look for when determining if you can be categorized as “potentially rich”.

1. Do you live alone? The most obvious indicator of lifestyle is where you live.  If you are living in a two-bedroom apartment with 5 roommates it sets off an alarm, whereas if you live by yourself (studio or not) we assume you must be making enough to afford that apartment, which is no small feat. And do you live in Manhattan? We also know that if you have that apartment in Manhattan, versus say Hoboken or Brooklyn, you are paying top dollar.  That’s not to say the outer boroughs are inexpensive (because they aren’t), but Manhattan portrays a certain level of success.  Each borough, and neighborhood, reflects a style that women (and men) make assumptions based on. The location of your apartment not only reflects how much you’re paying in rent, but also your cultural preference (or lack thereof). You should seek to live in an area that fits your personality and bank account.   For example, someone who lives in Williamsburg most likely wouldn’t want to live on the UES and vice versa.  (this applies to all cities, not just NYC).

2. What you do for a living. Let’s face it, she’s going to ask what you do for a living (most likely right before she asks how old you are) and you can’t really change your profession to impress a girl.  That being said, it’s all about the spin you put on it.  I don’t advocate lying, but if your job is on the lower end of the pay scale and has limited upward mobility, you can be vague.  For example, if you are a teacher (not to pick on teachers) you can say “I work in education.” If you’re not comfortable doing that for fear that she may respond with “what do you do in education?” I strongly suggest saying something positive about your job immediately after revealing what you do. For example “I teach high school science; I absolutely love it.” I find that so few people actually like their jobs that when we meet someone who does, we are immediately impressed.

3. Your watch and your shoes. As I’ve said before, these are two things women always notice and they are, or can be, very expensive. These items should be viewed as long-term investments that will last for several years, if not longer, and will be worn regularly.  Find the nicest watch that reflects your personality and make sure you take care of it.  If you buy a watch with a leather band, be sure to replace the band once it gets overly worn and be careful not to scratch the face.  You should also own at least one good pair of work shoes and one good pair of casual shoes.  Post college, sneakers are not an acceptable form of footwear when going out.  If you are looking for casual, easy shoes, check out Cole Haan, Sperry Topsider boat oxfords or classic boat shoes for the summer. (I will have a more thorough post on shoes in the future, but for now you get the idea).

3. Your car. As someone that lives in NYC, cars aren’t really that important or prevalent, but in pretty much every other town or city across America they are.  The thing is, most women don’t really know cars and therefore will only know the two extremes.  If you have a nice car, such as an Audi, Range Rover, BMW or Lexus, we assume you have money.   That being said, I am not recommending going out and buying a car beyond your means.  If you aren’t in a position to buy an obviously expensive car, your only job is to make sure you have a new(ish), clean, normal-sounding car.  Basically, just don’t have an embarrassing, piece-of-shit car that rattles every time you come down the street.   The key is to get a decent car and then take good care of it so it looks nicer than it is. It’s all about maintenance.

4. How you talk about money.  How a person talks about money and the things they have is not only a huge indicator or whether they actually have it, but also how they choose to spend it.  Any discussion of money on any level makes most people uncomfortable so I would avoid the conversation all together.   Also, any type of discussion about expensive things or events can very easily come off as braggy and unattractive – it will make you sound like you are trying to show off and prove that you have money.  People who really have money don’t need to talk about it.  The only women you’ll attract by bragging about  your wealth are real gold diggers. This also applies to your online profile and profile pictures.  If the majority of your pictures consist of you either standing in front of your expensive car or attending a charity polo match it will be clear the image you are trying to convey and it will just look like you are trying too hard.  On the flip side, if you complain about how expensive things are and act cheap, no woman will be attracted to you. It’s a thin line to walk.

5.  Your knowledge of wine, golf, skiing and global cultures. It costs money to travel, and golfing and skiing are two relatively expensive activities while wine is associated with sophistication and can also be quite pricey (think trips to Napa).  Being exposed to all of these things makes it seem as though you have the means to support these activities, as well as intellectual curiosity to seek them out (which translates to ambition). Lucky for you, it  is pretty easy to read up on different cultures and try pretty amazing wines without ever leaving the comfort of your home, while Groupon and similar sites have made  ski and golf getaways more accessible.  So go arm yourself with knowledge.

First impressions mean everything

Before the first day of school every year I remember my father telling me “make sure you make a good impression with your teachers because they are going to decide whether they like you within the first week of class.”  He was right. In fact, according to Princeton University researcher Janine Willis, people form an opinion of you within 1/10 of a second of meeting you and that impression can never be significantly altered.  Therefore, the most important thing you can do when initially approaching a women is smile and be normal.  This seems like pretty lame advice, but I am telling you, the key is to look your best and not do or say anything that would put her on edge.  Every woman loves attention so the mere fact that you are giving it to her  will make her happy- even if you don’t look like Prince Charming, it really doesn’t matter.  I think the best in-person approach is to make eye contact and say “Cheers” while holding up your glass or simply say “hello”.  It is that simple.  Online, you should keep your emails short, positive and to the point. I mean, why would you want to invest a lot of time on a email you don’t even know if she’ll respond to? The key is to write an email that forces her to respond with information she is comfortable sharing with a complete stranger.  You have to remember, even though online dating is now commonplace, women are still aware of the fact that they don’t know the person on the other end of those emails and therefore are a bit guarded.  An example of a good introductory email would be:

How are you? I really liked your profile. How long have you been in New York? What part of Connecticut are you from? I have family in the New Haven area so I’ve  spent a lot of time there. Hope you are having a good weekend and I hope to talk to you soon.”

Perfect.  It is straightforward, references my profile and warrants a response by asking me factual questions about my life, nothing too personal.  It also puts me at ease because he mentioned that he is familiar with CT, so it creates a bond with us- makes me think he is like me.

On the other hand, I received the below email.

“Subject: You can’t be serious…

Totally. Dig. The blonde. It kind of reminds me of a soft and shiny field of wheat, slowly waving in the field on a warm and lazy summer day — right before it gets harvested and processed into beer. Why beer? Who knows, I love beer. And you reminded me of it, which made me smile. Whoa, I just realized the enormity of that statement… your first impression ONLINE made me smile! I guess this is what they mean by love at first sight haha :)Sorry, bad habit — I just say/type stuff impulsively whenever they remind me of stuff — where are my manners, Hi I’m Psycho(ok, well that is my name for him)!

Let’s talk more — when are you usually free to chat?”

Seriously?! Maybe this guy has one of those personalities that is really quirky and endearing once you get to know him, but I don’t know him!!! Therefore I just find everything about his email offensive.  First off, you are comparing my hair to beer. Really?! If you are going to compliment anything about a woman’s  appearance you should say something unoffensive like “you have a great smile.”  That’s about it.  Everything else will come off as creepy and aggressive.   Secondly, don’t even joke about how we have a profound connection by referencing “love at first sight”- that sounds like something a serial killer says when he is kidnapping a woman.  He needs to stick to reality and not write whatever scattered thoughts come to him.  Lastly, by asking when I am free to chat he is A) presuming that I would want to talk to him on the phone and B) asking for my schedule, which is too personal for a first email- it makes me legitimately question if he would begin stalking me.
Therefore, gentlemen, stick to the basics, act normal and just smile and say hello.

Source: Association for Psychological Science 

Please send questions and comments

Please send any questions you want answered, stories you want to share or topics you want covered to  Also, I would love to hear any date recaps you would like to share- I will be happy to post it and provide my commentary.

Women, please let me know the most fun date you have been on.  Be specific.

8 things you should never wear

1. Short-sleeve button-down shirts. You shouldn’t even own this.  You shouldn’t even look at this when you are shopping for clothes.  Nor should you be seen with anyone wearing this.

2. More than 2 sprays of cologne.  Part of the allure of cologne is that we need to get closer to you to fully smell it. Keep it light.

3. Shirts or sweaters with a single hor-
izontal stripe
.  This style went out in the ’90s. Let it go.

4. Turtlenecks.  Doesn’t it feel like you’re  being choked by a very very weak child?

5.Leather jackets.  I know I am going to get a lot of disagreements on this one, but really, they are not flattering on men!

6. Graphic T-shirts or anything made by Ed Hardy.  The only t-shirt a guy should wear is one with a sports team/logo on it or one that is completely plain.

7. A jersey.  If you aren’t actually in the game and you’re over the age of 14 there is no reason for you to be wearing a jersey- grow up. Just wear a team t-shirt like everyone else. It looks trashy and as Jay-z said “I don’t wear jerseys I’m thirty plus. Give me a crisp pair of jeans… button up.”

8. Wife beaters.  Enough said.

contributing editor Dave Parkmont