Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

One for the Guys

Ok guys, don’t say I never did anything for you.

If you follow the instructions I’m going to give you today, you will be guarenteed better dates in the future.  Probably.  Unless you don’t need this advice.  In which case, attaboy.

Are you a man who is actively , or single and thinking that he’d like to get back into the pool?  Or single and sexually frustrated and thinking that he should get back into the pool, but doesn’t have a clue as to where to start?  If any of those descriptions might be appropriate for you (even a little) then you need to get your shit together and plan the perfect date.  A few perfect dates.

Even if you haven’t met a woman you’d like to take out yet.

You see, most women (that’s right – I just made a HUGE generalization) prefer it when guys have their shit together.  When they actually plan a date from start to finish.  When they say something like, “let’s get together on ___day for _____ at ____ o’clock” (for example, let’s get together on Thursday afternoon for coffee.  How’s 4pm?”).    It’s a turn-on.  So when I had that near perfect Sunday brunch date about a month ago, the thing that made it so great was his planning, more than him.

Now, long time readers will know that I’m a big fan of short first dates.  Or rather, first dates that have no obligation of lasting more than 30 minutes.  See this old post on ideas for more details.

None of those ideas take a lot of planning.  Just a little thought.  And what I’m suggesting is that you go ahead and think of it now.  Right now.  Sit down and plan a perfect date.  A few perfect dates.  From start to finish.  Where you’d like to go.  When (what time of day/day of week).  How you might ask. No, I’m not joking.  I’m suggesting that you think of the words you might use.  In much the same way that some people think through job interviews in their heads.

FYI, there is a reason I’m writing about this today.  I have a date later this week with a guy who seems like a great guy in a lot of ways.  Except that it’s one of those, ‘play it by ear’ dates.  We’re meeting outside a landmark and then ‘we’ll see what we feel like doing’.  I hate those kinds of dates.  Really hate them.  Sometimes they work out fine.  But usually not.  Usually they’re annoying and I end up thinking the guy is a flake.  And so I’m going into it thinking not so good things about him because of the date that he pretty much hasn’t planned.

Guys, do yourself a favor and plan ahead.


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18 to “One for the Guys”


  1. Singlegal says:

    I just cheered in my seat! Now my coworkers are looking at me funny :-)
    BRAVO!

  2. Sarkie says:

    Well my best dates, are the ones that start for a quiet drink at 2pm, and finish at 11pm spending all day with each other. Meeting at a bar we both knew, then going from place to place not knowing where, but each other.

    But then there are the dates where you want stuff to be planned, but say a first date was planned out and I’ve put in all this effort, for location to location to location, and you knew it wasn’t going to work out. Would you still want to go to every place I’d decided on going?

    Play-by-ear = end of first bar, “well i gotta be going now, really sorry” excuse, rather than, “sorry we can’t go white-water-rafting I’ve got to go now”.

  3. Catherinette Singleton says:

    Woman, I couldn’t have said it better my self. There’s a total WOW factor when a guy has a great idea for a date.

  4. aGirlNamedMe says:

    I like a plan. However, when dating, if the plan is too orchestrated, I get the impression that he’s been here, done this before – lots. And I find that distasteful. So….a loose plan is good, but not planned down to the last detail.

  5. pansophy says:

    And herein lies the problem – all women are different. Some women want there to be a plan whereas other women would find the same plan as a sign of the being too rigid or ‘orchestrated’ or whatever.

    So personally, my advice to guys is to learn to listen because women will tell you which kind of woman they are (even if they don’t say it directly). Have a plan, have a backup plan if she doesn’t like the plan, and be willing to give up the plan altogether.

    Having said that though us guys have to think about ourselves too. Do we want to be with a woman who wants a plan, never has a plan, or is somewhere in between. So in many respects how the first date is ‘planned’ (and how everyone reacts to it) is a good indicator of what life would be like with each other, and isn’t that what a date is for _ to figure out if you are compatible?

    So yes, I agree one should do things to set up a date for success but it has to be congruent with who you are and if that makes for a poor date then you probably didn’t have much chance anyway.

  6. Erin Korogodsky says:

    I think the “fly by the seat of your pants” date kinda says that they can give or take you from the very beginning. And I’m a little tired of that attitude. I understand it but I am a little tired of it. To get to know me, you’re going to have to make an investment. Its a very small investment, with huge returns but if you’re not even willing to make some kind of plan or investment in the beginning, what kind of attitude do you really have? I don’t want to be more spaghetti that you’re throwing against the wall to see what sticks. I want someone who’s genuinely interested in getting to know me and who I’m genuinely interested in getting to know.

    Here’s a refreshing change of pace…

    The other day, I was talking on the phone with a new guy – someone who I connected with online and we were planning to meet up. He said, “why don’t I be a man and make a plan for Thursday evening?”

    It has been a long time since anyone spoke to me that way – politely took charge to do something nice for me – and I loved it. Then a few hours later, he sent me a text with the name of a restaurant he wanted to take me too. I was turned on and intrigued even before we met.

    When the night came around, we both had worked late, everything got turned upside down and we ended up walking around a little aimlessly until we decided on a restaurant that I loved and he’d never been too. It was very nice over all but I have to say that his attempt to plan something out was still a highlight. Even though it didn’t work out, I loved that he found the balance between wanting to plan something special and also wanted to pick something I’d like.

    Thank you for this blog – I always relate to your posts and it makes me feel great to know that we’re all going through the same things out there :) -Erin in San Francisco

  7. aguy says:

    Well, obviously girls would like it if guys would plan out dates from start to finish. I’m sure you’d like it even more if we also brought flowers and hired a driver to pick you up! But really, I’m not that interested in putting a lot of effort into a girl until I know her a little bit and have decided she is worth it. First dates should be short, easy and low-effort.

    That said, suggesting meeting by a landmark is pretty lame. Even if you don’t know the area, it takes two minutes to find something on Google Maps or Citysearch.

  8. lostplum says:

    fly by the seat dates work but only when it comes down to picking and the guy actually has ideas (doesnt have to be exactly planned) but if you are out and decided food, or drink, or whatever he should know ideas “then” make a plan!. Nothing is worse then the guy flying by the seat of his pants and it ends with “umm….I don’t know/I don’t care”

  9. amberying says:

    The problem with the “Let’s see what we want to do” date is that it feels like it lacks confidence. Whether or not the guy actually has his shit together, it feels like he doesn’t. Even the coffee/brunch date, as common as it is, is more appealing than that.

  10. My Kafkaesque Life says:

    I’m definitely a planner. I think I should be more spontanous.. Sometimes that’s really better, because if it’s too scripted, one can appear stiff and boring. But every woman (and man) is different, so there’s no general answer to this.

  11. Tales From A Bar Stool says:

    For first dates, it’s definitely best when the guy has a plan in place. But for future dates, I like the “fly by the seat of your pants” approach thrown in every so often. Guys definitely need to put more planning and thinking into their dates. Grow some balls…

  12. @luckychica says:

    Hooray! You’re right, plan the freaking first date! No, it should not be scheduled down to the minute. But a solid location and time are key. At least 2 days in advance. And a landmark doesn’t count. I don’t want to meet you at location X when we might end up on the other side of town or at a beach or park and I’m the asshat in heels.

    This doesn’t mean (as one commenter suggested) that we would also like flowers, chocolate, a chauffeur and commitment. Just plan the first freaking date like you made effort, but not like you do this for a living. Be a man with a plan.

  13. Simone Grant says:

    -Singlegal
    I hope you told your coworkers to go to hell :-)
    -Sarkie
    That’s an awfully long first date. Awfully long. Longer than I’ve ever been on. Well, if that works for you.
    -Catherinette
    That’s what it is – a WOW factor. It’s like any guys who take five minutes to think ahead will automatically move to the head of the line.
    -aGirlNamedMe
    I don’t really know what you mean by “planned to the last detail”. If a guy says, “How about we meet at place X at 7pm on Thursday for drinks?” is that planned to the last detail? ’cause that’s all I’d really like from a guy – time, place, date, action. Not a script.
    -pansophy
    It’s true. I’m sure there are women who’d prefer a completely laid back, “let’s meet outside the X building and then see what we feel like doing”. But I’d say they are in the extreme minority of women over the age of 21. Extreme minority. If a guy needs to be with one of those women because those are the types of dates he feels most comfortable with, then he should definitely stick to his guns and try to find one.
    -Erin Korogodsky
    First thank you and welcome. You make an excellent point. When a guy doesn’t make a specific with me, I ASSUME(whether that’s an appropriate assumption or not) that he’s not that into the date. Whereas when a guy makes an effort, I assume he is into the date, hence into me. Both of these actions affect my behavior – whether or not they “should”.

    The story you told reminded me of a date I had not too long ago. We had concrete plans to meet at a very posh cocktail bar (one I quite like, though it was his suggestion). And then the night came along and it was pouring rain and miserable out. We spoke early in the day and decided to shelve those plans and go to a pub that wasn’t that far from either of our apartments. It wasn’t a great date, but I really liked his flexibility and thoughtfulness.
    -aguy
    Obviously? Um, no, I wouldn’t want anyone picking me up for my date. And I agree that first dates should be short. But I can’t find your point. You don’t think you should make any effort towards first dates. But the guy I’m going out with later in the week is a loser for not making an effort? And, btw, everybody is WORTH an effort of some kind. It’s called respect.
    -lostplum
    I’m fine with meeting in an area that’s dense with bars or restaurants and having him say – here are my 3 favorites, are you interested in any of those (or something like that). But IMO, the fly by the seat of the pants dates usually end up with the guy being clueless and me getting annoyed.
    -amberying
    I’m a big fan of common. Maybe that’s the problem. Maybe guys think that women need to be impressed with some special event. I’m perfectly happy with meeting at a decent coffeeshop (plz no starbucks). And yes, it comes across as a lack of confidence.
    -My Kafkaesque Life
    Again, I’m confused by this concept of scripted? Please explain.
    -Tales From A Bar Stool
    Certainly, once I know someone well then I’m fine with just figuring it out as we go along. But not with someone I don’t know.

  14. csteen85 says:

    My first date with my current boyfriend was planned by him and it was a surprise. We hardly knew each other, but we met at a mutual friends’ wedding. He planned sort of a Marathon Date that involved the Central Park Zoo and a favorite Mexican Restaurant, then we mutually decided to go back to his place. I’m not really that type of girl, but I’ll be completely honest – I was so impressed with his thoughtfulness that I couldn’t resist. :) Great Blog!

  15. Definetelymaybe says:

    Yes,I agree with you. Things should be planned. I’m seeing a girl now, and our first date was last Thursday. I planned everything out from A to Z. I knew that she likes the outdoor seating, so i took that into consideration and picked the place.But i also assured her that i could change the plan if she wants to go to a specific place, like her favorite bar or restaurant. What I wanted to convey to her that I’m flexible and wiling to adopt her suggestions as well. Anyway, we met and everything went according to my plan. So the date was a great succes(: not only was it planned but also we were connected in many ways. She loved the place, the conversation between us, the wine and every aspect of that night.
    Once again, i do agree with you. And respectfuly, i would like to add a few points for guys. Try to “communicate” with the girl before planning a date. Then plan the date based on your input and use your “own” judgement to make this plan more colorful, and more suitable for “her”. I think if you win her heart geniunely, only thing she cares about will be you, more than the place or whatever honest mistake you might make -regarding the planning- on date. Don’t try to look posh. I think how sincere and thoughtful you act will send more “true&natural” signals.
    Thanks for another great dating posting you brought up.
    Bravo!

  16. aguy says:

    I guess I was just saying that I didn’t see the point of planning out a perfect date in my head “from start to finish” like you suggested. All you really need is a time and a place for a first date … I once had a very nice first date with a girl from an online dating site at a Starbucks convenient for both of us. It was short (and sweet) but we saw each other again soon…

    Of course if I end up liking a girl I’ll make more of an effort … but by then I’ll know her a little bit and can hopefully come up with stuff I know she likes to do…

  17. klawless says:

    The old adage “Aim at nothing and you’ll hit it every time” comes to mind.

    I’m with Pansophy in making a plan based on your communication with your date and having a back up (or two) ready just in case. Whether the girl likes spontaneous or not… a first date almost always works better with some guidance behind cupid’s bow and arrow.

  18. Simone Grant says:

    -csteen85
    Thank you and welcome to the blog. I agree, there is something very sexy and kinda irresistible about a guy who makes a big effort.
    -Definetelymaybe
    And welcome to you to. Thank you for the thoughtful comment. I agree, it’s important to communicate and listen. Not everyone has the same opinion of what makes a good date. It’s impossible to know that without communicating first.
    -klawless
    I love that, “aim at nothing and you’ll hit it every time”. Sadly, I think that that’s the attitude so many people have with dating – men and women. People barely even try. And the standards for how supposedly grown adults treat one another are SO low. Ugh.