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I am adding the following disclaimer to all of my dating related blog posts.  I change details, and create composite characters when I write about dating archetypes such as “Mr. Houdini, Mr. Angry, etc.  I would hate it if someone wrote about a high energy blonde comedian negatively in a blog, so because of that I never include a person’s occupation or anything about their physical description.  I also change enough details that I doubt anyone I am referring to would even recognize themselves if they read one of my articles.   I have split one person into three, or taken several people and put them all into one example.  So simply put, I am very ethical on this blog.

A happily married friend suggested that I should write this list because as he put it.

Some men just have no clue

And because I get a lot of men on this blog searching for all sorts of knowledge about dating, I thought I would give it a shot.  So based on my experience and an extremely unscientific poll of feedback from my female friends, ranging in age from early 20’s to late 50’s I came up with this list.  Many of these are obvious and universal as they apply to both genders.  And mind you I am far from the “perfect” dater.  I make every mistake known to man…and then some.  But in the interest of the public good….here we go.

These tips apply to when you are actually on a date with a woman…not before.  Online dating tips are another thing entirely.

Tip #1 – Don’t forget to compliment the woman on her appearance.  You don’t have to say much but you had better believe that whomever agreed to go out with you or meet you for a drink has spent a great deal of time on their wardrobe, hair and makeup.  Even the less is more type of gal is going to want to impress, so a simple, “You look nice” or “You look lovely” will do.  It is always a huge mistake to say nothing, especially on date number one or two when you barely know the woman. When a man says nothing to me, I assume he is not that interested.

Tip #2 – Don’t look cheap – You don’t have to spend a lot of cash, it can be as little as a drink.  Under no circumstances go dutch.  It is just rude, especially on the first date and especially if you were the one asking her out.  You don’t need to buy an elaborate meal, and you don’t need to spend a small fortune.  But at least OFFER, she may decline but it is a nice gesture.   Even if you think that in 2012 you shouldn’t have to do this,  it is simple common courtesy to offer something even just a cup of coffee or a glass of wine.

Tip #3 – Don’t bitch about ex-girlfriends or ex-wives – I am extremely guilty of this one – just don’t do it!  It is best to keep things light.  You might mention the divorce or breakup, but then do not bash your ex or go on and on about her.  It just makes a woman feel completely ignored, and as if she is some type of free therapist…BAD FORM.  When men have done this to me, I might feel sorry for them, but I don’t take them seriously as a potential partner.

Tip #4Don’t complain about money, that you have no money, or that you are broke…even if you are broke.  Again, you need not be a Rockafeller to impress your date.  I know of countless lower income men who do quite well with the ladies.  When you bitch about your finances you might make the woman uncomfortable, or feel obligated to somehow take care of you.   It is a lot of pressure and totally inappropriate.  You can bring this up later, but when you first meet someone, it’s generally a bad idea.

Tip #5 – Don’t start talking about sex too soon – Now this one is true in most cases unless you met this woman on a hook-up site or for the express purposes of just having sex with her.  In most cases you will just freak out your date and she will want nothing to do with you. If she brings the topic up first, then its different.  Never assume however, that sex talk will lead to sex.

Tip #6 – Don’t text or talk on the phone in front of your date – If it is a work related or family matter, get to quickly and get back to the date right away.  It’s best to physically walk to the bathroom, or to another area when you do it, then apologize profusely and get back to you date.  Don’t make a habit of it, and don’t constantly check your email or text messages in front of your date.

Tip #7 – Don’t go on a bitch fest – So many times I have sat down at a table with a perfect stranger and they just go off on some rant about their landlord, their job, their neighbors or any number of things.  It makes a horrible first impression and it is best avoided.

Tip #8 – Don’t go down a laundry list of questions – Sure everyone loves to talk about themselves but you can make a person feel interrogated when you simply throw one question right after another.  A date is not a job interview relax, talk about something light like the weather.  Also wait for her answer.  I can’t tell you how many dates I have gone on where a man asks me a question, only to cut me off before I answered it.

Tip #9 – Avoid lightening rod topics – Again obvious, but you would be surprised what I have heard from friends: abortion, politics, rape, religion, avoid anything that might alienate you from your new potential partner.  It is one thing if you already have a good idea of the person’s religious or political beliefs from an online dating profile or if you know you have similar beliefs.  But this is not time to preach or convert, if you never want to see the woman again, then this is a sure-fire way to make that happen.   And don’t ask your date if she wants children on a first date – you are putting her on the spot and it is WAY too early to worry about that yet.

Tip #10 – Don’t ask about her former boyfriends or how many sexual partners she has had – This one is just plain rude.  A general rule of thumb is if you wouldn’t feel comfortable answering something don’t ask another person.  And although men might like to brag about how high their number of partners might be, women are usually the opposite.  There are always exceptions to this rule however as some of my female friends make no bones about having a plethora of partners.

Tip #11 – Don’t take her somewhere where you can’t talk – Movies are terrible as you won’t engage in much conversation, as are many music venues.  Keep it simple, but make sure you get to talk if this person is a relative stranger to you.  You might find that she will like you MORE if you actually talk.  Rather than taking her someplace impressive where you will barely share a few sentences between each other. Again if you are just intending on having a sexual relationship with her and not much more, than go ahead and take her to a loud club.  You might confuse or annoy a woman who is looking for a hook-up if you ask her to go on a traditional date.  She might just want to have sex with you and skip the formalities – but make sure you are both want the same thing, before assuming anything.

Tip #12 – Don’t bring up another woman you want to go out with – Think I am kidding on this one?  It just happened.  A somewhat nervous man trying to forward the conversation openly admitted to correspondence with another woman (one I happened to know) on an online dating website.  She happened to be a comedian.  He said he hadn’t gone out with her yet, but was hoping to eventually meet her because he found her fascinating.  I couldn’t make this one up….NEXT!  I have made the mistake of talking about past men, but never a man I wanted to go out with in the future – that is madness.  It’s also tacky to tell a petite woman how much you have a crush on a celebrity that is tall and curvy, the same goes with going on and on about how hot a tall and slender blonde celebrity is when you are on a date with a shorter curvy gal.  Like it or not she is going to make the assumption that whomever you are describing is what you prefer.  DON’T COMPARE YOUR DATE WITH ANOTHER WOMAN.   After you have been dating a while this kind of talk is fine. But when you are just getting to know someone just don’t go there, unless of course you are describing some celebrity your date happens to resemble then it’s not so bad.  I’m a taller than average athletic blonde, when some guy goes on and on about a curvy brunette who is 5’2″, my heart sinks.

Tip #13 – Don’t force her into a socially awkward situation – Don’t also try to meet up with friends, and then force your date to hang out with them.   Your date is essentially a total stranger to you, shoving her into a social situation with a new person, or a bunch of new people is just going to make her more anxious.  When you make the date, and force your date into meeting more new people because it is convenient for you, you are essentially telling your date that she is not that important.  It is a bad call, rude and it shows you have no game.  A first date is not the time for multitasking, if you blow it, you probably won’t get a second chance.  If you would rather see your out-of-town friends, then don’t plan the date on the same night, or end the date and then go hang out with your old friends.

Tip #14 – Don’t openly criticize your date – Look these situations are strange for everyone, for you and your date.  It might take a minute for you both to calm down and really start talking.  If you make a judgment on your date, she will most likely shut down immediately and just want to leave.  And no one wants criticism like this, especially from a virtual stranger and when they are vulnerable on a date.  If your date is being overtly rude to you, it might be time to just end the date and go home.   But if you WANT to see this woman again, don’t pick her apart.  This might seem like common sense, but it happens more than people think.   I have heard way too many stories and had my own experiences with this one.  Personal pet peeve – Hey I thought you were a comedian, why aren’t you funnier? – Well maybe because I am not ALWAYS working.  If I here that particular question one more time…

Tip #15 – Never assume you are going to have sex – This should be obvious but I thought I should write it anyway.  A woman is under no obligation to have sex with you, make out with you or even kiss you – even if you have paid for dinner and drinks.  You might think the date is going extremely well, while your date might never want to see you again.  Some women will go along on date out of a sense of politeness, some will send mixed signals, and some will be downright confusing – it’s all part of the game.  I’ve heard stories of women grinding into men on the dance floor, making out in bars, or kissing for hours in cars who will ultimately say no to sex. You only get to have sex with a woman if she agrees to it.  This is true regardless of the amount of time you spend with her, the amount of effort you put into the date, or even if you spend a fortune on the date.  No always means no.  If you just want to hook-up with a woman, you should make your intentions clear early on.  She may not want to go out with you on a traditional date anyway. Some women are perfectly fine with just sex, but communication is key.  Never assume anything without consent!

If anyone has more tips for me I will gladly add them.  🙂

19 comments on “Dating in NYC: What Men should NOT do on a first or second date.

  1. Joe

    I know (think) that you have probably gathered this information from personal experience. But I just could not help but be saddened that you would have to write an article about it.

    Your comments say so much about how poorly men have been socialized in this society. Or how rampant the runaway ego is that dating men would come off so poorly.

    It not only speaks poorly of men in the dating scene, but I cannot help but think that these boorish behaviors spill over into other milieux.

    Thanks for writing this. Perhaps judges should pass this out when they adjudicate divorces.

    Whew! “What a revoltin’ development this is!” (William Bendix, Life of Riley)

    1. julietjeske

      Women can be just as bad if not worse on dates. I have heard horror stories from the other side of the fence. Some women get really materialistic and demand that some man spend tons of money on them, or they only ask about financial things etc. But I just went on a date that was just flat out weird in that it was nothing but mixed signals. I didn’t really wake up out of my daze and see it for what it was until the next day. I gave him the benefit of the doubt in that I thought he might be socially awkward but I think he was just inconsiderate. I liked the guy so I wasn’t thinking clearly, but he treated me poorly and I should have seen the forest before the trees, oh well.

      I am hardly perfect as I ramble, I talk about my cats, I talk about my divorce, I am nervous…I have tons of bad habits on dates. But I try to not be cruel or lead a guy on when I am not interested. At least I get that part down. If anything I am extremely straight forward when I am not interested, very few men get the wrong idea when it isn’t working.

  2. Captn Scorp'yo

    Very good list. And, yes, a lot of these are just plain manners, and not gender-specific.

    Important corollary to #2 is that it can be very bad for a man to *insist* on paying for anything (especially over objections). Depending on the date in question, this can come off as insecure/patriarchal/controlling. (Of course, some like that.)

  3. Anders

    This, my comment, actually reflects what I don’t do but here it is.
    Learn the art of short lines and release small amounts of your story at each occasion.
    Everyone likes to talk, even the ones that don’t do much of it. What people really want to talk about its themselves in one form or another, YOUR INTERESTS COUNTS AS YOURSELF. Everyone want’s to be seen and listened to.

    I just realized, that unscrupulous people use this listening technique to hide information about themselves and find out things about others. Well, watch out for that too.

    Thank you for an excellent blog it makes me think every time.

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  5. Megan

    Overall, this is a pretty good list, but it is disheartening to know that many men today simply have no idea of what is considered proper conduct on a date.

    Here is what I disagree with:

    Tip #1 – Don’t forget to compliment the woman on her appearance.

    I know I’m good-looking and I know he knows it too since he asked me out. However, I am more than my looks. I have a brain, a personality, feelings, hobbies, etc. Since women are exploited and valued primarily for our looks, I love it when the guy shows me that he is concerned about his looks too and that he has a good sense of style by the way that he dresses on our date. Men always compliment us on our looks, so how about stepping away from the norm and the banal, and looking for some depth. A better tip here might be for the man to put as much into his appearance for the date as the woman did.

    Tip #4 – Don’t complain about money, that you have no money or that you are broke…even if you are broke.

    If my date is literally broke, this is something that I want to know upfront so that I can either 1) end the date early or 2) make sure that this is our last date. Why? Because since he’s broke, he needs to concentrate on stabalizing his financial situaion and securing gainful employment before he can have any kind of meaningful relationship with me. Financial issues are one of the top three problems citied by married couples for divorce. That’s an excellent indicator of what will happen in a romantic relationship when someone is broke. However, if both people are broke, then there’s a perfect match lol.

    Tip #5 – Don’t start talking about sex right off the bat.

    This tip I disagree with because I like to know what I’m dealing with from date number one. If it’s our first or second date and he talks about sex right off the bat, he is simply letting me know who he is, what’s on his mind, and what his priorities are. I like realness early on to avoid wasting time. Again, this would be our last date.

    1. julietjeske

      I have to run to a gig, but I really want to strongly disagree with you on the looks issue. I understand your point of view, but I am a size 4/6 blonde woman who looks a good 10 years younger than my actual age. I even worked as a model briefly when I was younger. I spend a tremendous amount of time on my appearance, I work out, get my hair high-lighted, I spend most of my disposable income on my clothing and I don’t think it is a bad thing. I like to look nice and I love clothes. And I have been on several dates, even second dates and the assholes don’t make one comment. Yet I will compliment them on their appearance. It is really rude. I can’t stand it, and it just makes me think the men aren’t interested. A simple “You look nice” is all that is needed. Especially when someone has spent time trying to look nice. But I usually get nothing. That is just rude. Doesn’t matter on the gender. For example a man I recently went out with wore a sports coat, and I complimented him on it. I was in a dress and heels, and NOTHING! It was tacky on his part. I am just sick of it.

      So I see your point, but I still disagree with you. As far as the cheapness and sex comments they are all a window into the man’s soul. But I do think that dating behavior on the part of men has gotten so bad, that they need to know these things. So many men are frustrated and I have been on so many bad dates, couldn’t tell it to their faces…so I made this list.

      1. Megan

        This ranks right up there with a “you smell good” comment. This is just the way that I see it. Looking/smelling good is to be expected on a date. The point, afterall, is to put your best foot forward. I think this is more of an issue of needs or validation for you. We all seek and require validation in different forms. The looks department is your form of validation which is fine, but it sounds like the guy in the sports coat wasn’t so much a jerk as he simply doesn’t share the same types of needs that you do which is validation of physical attributes through a compliment.

        1. julietjeske

          Everyone is different. For me I find this type of behavior quite rude. And it only takes two seconds and for the most part causes no harm. It may boil down to preference but even my 89 year old grandmother blushes when we tell her she looks lovely. It is just common courtesy, if someone says “Why you look nice” to return some type of compliment, not to just stand there and say nothing, especially when it is OBVIOUS that the other person spent time getting ready for the date. Not all men and women bother…I have heard some stories. The sports coat guy also asked other rude questions which I won’t rehash here, but he basically didn’t know the definition of agnostic. I felt like I had to defend my non-religious beliefs. He was lame. The date was lame. And he was rude.

          1. Megan

            Yes, that’s my point–everyone is different and has different needs which is why I said that you and sports coat guy have different needs in terms of validation. But I think you could use experiences like that to determine whether you want to follow through with a date or not since it’s a huge turn off for you…if you are about to go out with a guy and he doesn’t compliment you on your appearance, then why not just stop things right there and tell him this won’t work? That way, you have saved yourself much aggravation.

          2. julietjeske

            Hey I allow people to be human. It isn’t just one flaw…and then forget about it. I do think it is good advice though as usually a “You look lovely” comment is not going to HURT a guy. Most men make so many obvious mistakes…it just gets old. I think MOST of them have no idea how to date or act on a date…that is the ones who are still single at my age. That is why my happily married male friend helped me with this list. He knew what he was doing and that is why he is happily married! Ha! 🙂

    2. Joe

      As a male I cannot condone any of these negative male behaviors. My concern is with causes.

      How have males been socialized to be so ego centric with respect to interacting with a female?

      Is it a matter of utter insecurity in the face of a polished female date?

      Are these males in the minority or tending toward majority?

      Whose responsibility is it to socialize and help these males develop authentic personalities and character?

      What has gone wrong?

      How might it be fixed?

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  10. goddessofwhine

    Hi Juliet, Thanks for writing this article. I’m a fan of your blog. Could you add tips about how to dress on first dates or dates in general? I live in South east Asia and it does get hot and humid here but turning for a date in slippers and jeans to a restaurant, even a casual one is just a no-no. Looking forward to more of your articles! 🙂

  11. Sex Dating

    Wow… I love reading this article! Very true! 😀
    I had a date before and it’s our first date. He brought me to a movie! WTF!!! 2 hours of awkward moments! No conversations and I’m not that stupid not to sense that he’s not really watching the movie because he’s so busy thinking how and where to touch me! WTF! -_-“

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