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

My Date With the Very, Very Nice Man

“Back from my early date. He was a very, very nice man. A good guy. And cute. I wish I knew a very, very nice women to introduce him to.”

I tweeted that last night, shortly after I got home from my date.  Just to be crystal clear, it was a perfectly fine date.  I enjoyed his company.  We had a pleasant conversation.  The bar he selected to meet at was a place I quite like, convenient for me… I have no complaints about the date.

Anyway, my tweet received several replies:

@singlegirlie, “Uh oh. Too nice?”

@bobmatnyc, “LOL! Not bad enough for you, eh? :-)

@Sean_Oliver, “and another bites the dust. He didn’t want to play “toss you around the apt?”

@ecined, “Pack him up and ship him to Arizona?

@ambilevous, “you have no idea how much it sucks to be on the receiving end of something like that”

@derekscruggs, “More proof that nice guys finish last?

@silentific, “Classic nice guy #fail RT @SimoneGrant: He was a very, very nice man. I wish I knew a very, very nice women to introduce him to.”

@Dzubak, “You girls and your nice guy drama ! I want a specific of nice on this one please. ??”

@KB_in_NYC, “I’m nice. Then again, maybe not so much. I think I have the same nice guy aversion thingy you do. Sigh.”

So here’s the deal about me and “nice guys”.  First of all, I prefer kind to nice.  Kindness is an essential quality I look for in a guy. I can’t love a guy who isn’t kind.

That said, here’s the thing. And I realize that this is something that a LOT of my readers just won’t be able to relate to.

I’m an ex-punk. I mean that literally. I had pink hair. And purple hair. And orange hair. And bits of hair shaved off so you could see my skull.  Oh, and crayon red hair. That was my favorite. There were many years of my life when all of my clothes were black. I have done things, some of them not-so-long-ago, that I would never admit to most of my friends.

I have not been a good girl.

For most of my teens and 20s I was absolutely certain that I would never live to see 30. Not just me.  My friends felt the same way (which is freaking hysterical because my closest friends from back then, who are still the people I love most in the world, are corporate VIPS now). But it was actually pretty reasonable for us to believe it then.  We’d already lost some of the people we loved. And we knew others who were HIV+ (which back then meant something different than it does now).

And then we hit 30 and we were still alive.  Not only alive but doing well. Whoulda thunk it?  So we started to follow some of the rules, sometimes.  Started to think about the future.

The way I see it, the people in my generation (which I vaguely see as very late 30s to early 50s – which is, I guess, more the people in my social sphere than the people in my generation) fall into 3 groups:  Group A is like me.  We never thought we’d make it this far.

Group B are the rule followers. They were the good kids. The ones who always did as they were told. And they turned into rule following adults.

Group C started on the same trajectory as Group A.  They jumped in every puddle, drove their parents nuts, etc. But at no point did it occur to them that they were, indeed, still alive. That as sad and challenging and unfair as reality is, they could make their lives into something.  So they continue to destroy their bodies, minds, relationships , jobs with self-destructive behavior because they are absolutely certain that none of it is worth shit.

I’ve tried, really I have, to have relationships with guys in Group B.  And it just can’t work.  Our brains just work too differently.  I challenge everything. I’m always asking WHY.


I don’t think I’ve done a very good job in explaining this.  Look, it’s not something wrong with nice guys.  I don’t find them unattractive in any way.  It’s about who I am and who they are and the lives we’ve led and the way we process the world. Differently.

ps.  Men from Group C need not apply.

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45 to “My Date With the Very, Very Nice Man”

  1. brewers_rule says:

    Here’s the thing you’re missing about Group B: there comes a time, and in some cases that coincides w/a woman that’s “fun,” B guys love to release their inhibitions w/at the end of the day after following 99% of the rules. Rules have their place, as does breaking some. Just a question of which you choose to follow or break along w/when and where you break ’em (Can you tell I’m a Group B guy?). Isn’t that the place the term “Always the quiet ones” came from? I would think that would be a fun undertaking to not only see, but elicit from, Group B guys. Hate to sound mean here, but I’m sensing some laziness here from someone who claims to wanna continue having fun 😉

    • Simone Grant says:

      I don’t think you sound the slightest bit mean :-) I do think we’re talking about slightly different things here. This isn’t really about wanting someone who is inhibition-free. Who likes to cut loose and have fun. This is about finding someone I’m compatible with, whose belief system is similar to mine and whose life experiences have been somewhat similar to mine.

  2. Izzy says:

    Wow. I absolutely loved this.

    Thank you for sharing it and digging deeper. You really hit the nail on the head when you say, “First of all, I prefer kind to nice. Kindness is an essential quality I look for in a guy. I can’t love a guy who isn’t kind.”

    I will tell you that I am a mixture of A/B. I’ve done some ridiculous things in my young life (mid 20’s) but my friends always consider me the cautious one. In comparison, yes I am cautious, but the kids in Group B would think I was a little crazy anyway.

    I’ve found that when I date guys from Group B, I appreciate them for who they are, but also understand that they will never “get’ where I come from. Perhaps we aren’t giving them a fair shot, but in my past relationships/dates I hate getting looked at like I have three heads. The guy that works for me is a little rough around the edges, family is a little strange, and also kind/respectful. If you find one that fits the bill pass him along?

  3. jamy says:

    I don’t know why it troubles me, but clearly there are people who fall into some other category (or many others!). I mean, I guess I’m in group B, but I used to be an activist (of a sort), have left-wing views, am much less of a consumer than most folks…though I am still relatively conventional. I would hope that you might find a guy who is somewhere in between A and B–that’s where I fit and I figure there must be guys out there like me too. (Not that I have much luck finding them!)

    • Simone Grant says:

      Any attempt to group people is an oversimplification, at best. I do think there are 3 overall groups and that it may be specific to people in my age group because we were caught in the middle of some major societal shifts. But I know that lots of people don’t fit neatly into one or another. The whole grouping exercise is really just a way for me to explain why I am more likely to click/be attracted to some men than others. Nothing more serious than that.

      • jamy says:

        We’re the same age, so that’s not the reason I see this differently. Maybe I just would categorize people differently if I were try–but I haven’t.

  4. Christian S. says:

    A understands and challenges you

    B can’t see you for who you are

    C has a different goal in life than you (none)

    P.S.: why do I always have to think of Valerie’s letter when reading your posts?

    • Simone Grant says:

      You hit the nail on the head. Squarely. I seek a man who understands and challenges me and I firmly believe that a guy with life experiences and a worldview similar to mine would fit that bill. I also believe that a man who has spent most of his life following the rules/NOT questioning authority will never really be able to see me for who I am.

      Thank you. Sincerely. Thank you.

    • Simone Grant says:

      Valerie’s letter?
      I’m going to have to ponder than one.

      • Christian S. says:

        “[…] what I hope most of all is that you understand what I mean when I tell you that, even though I do not know you, and even though I may never meet you, laugh with you, cry with you, or kiss you, I love you. […]”.

        I do meet lots of really interesting people lately – still I don’t encounter the genuine attitude of mind to accept others for who they are without wanting them to accept “their” point of view very often.

        Maybe my heads way of trying to express “Thank you. Sincerely. Thank you.”?!

    • Kayle says:

      OMFG, this is the first person who’s nailed it. Can you please fix the entire self-help genre and stop their “she just likes being abused and is a sicko” bullcrap??

      The other hting that is hindering decent matches is that people actually believe this crap themselves and go hunting for particular groups according to stereotypes instead of growing up and knowing people. It’s a rather nasty cycle.

      And hi. late in the game.

  5. LAguy says:

    So what separates nice from kind?

    • Simone Grant says:

      Ah semantics…
      In my words, nice is action. Nice is shallow. Nice is facade. Nice has nothing to do with truth or feelings. It’s conforming to society’s rules for polite behavior.
      Kind is caring. Kind is meaning. Kind is feeling and warmth. I seek a man with kindness in his heart.

      There are many people who’ve said it better than that, I’m sure.

  6. Laura says:

    I probably fall into Group B as well and would probably be into a Group B guy (or a mix between A and B) but the nice vs. kind debate did get me thiking.

    I’ve never really thought of it before but I definitely prefer kind/respectful (like Izzy said) but when it comes to nice guys I get board quickly and opt out of those relationships.
    If a guy is too nice there’s a good chance I could hurt his feelings or break his heart too easily so I tend to walk (run) away from those situations.

    As a side note, it’s always a bit funny when you’re on a date and think to yourself “I wish I knew someone who would like him, because he’s just so nice!” Haha. 😉

    • Simone Grant says:

      OMG, I was totally thinking for most of the date that he was such a great guy and I wish I knew the right girl for him. I’m still thinking of it. It’s kind of a horrible thing to be thinking, though :-)

  7. Terry says:

    I applaud your effort to make categories – boxes – sometimes they even work.

    Once again, no advice for you with this one; but I never have advice. I think it is simpler – I think we can look to backgrounds and see why people cannot see us as we are, or as we were – or relate – but still exceptions make rules– bla bla bla.

    Face it- sometimes it clicks, sometimes it doesn’t. We can try to explain it- and someday we will have better definitions than today. So, don’t beat yourself up over it– nice guys, or kind guys don’t finish last. If they don’t click – well, they don’t click. You can analyze it – but most of the time our analysis fails us, and may not be helpful.

    When you try to make something work- because you really want it to for whatever reason you convince yourself – well, in my experience it is just a tragic result. I think what you are saying is you don’t want to “make” it work -.

    It’s ok. Three weeks ago I saw a little old lady at the Biltmore Mall here in Phoenix. She was beautifully dressed. She was about 5 foot (maybe was once) – she was thin, had a walker – was working hard. In the middle of her gray hair was this bright, fire-engine red streak that she had put in. All I could think was “That’s a lady who is struggling against her body but knows how to live.” Somehow- now I think of you- in 50 years I hope you don’t forget that spirit – and wherever it resides in you, its ok to let it out.

    • Simone Grant says:

      Yes, sometimes it clicks and sometimes it doesn’t. I don’t think it’s a complete waste of time to analyze the whys, but maybe it is. I’m frequently wrong. I’d like to think that if I live to be a little old lady I’ll be walking around with a streak of something in my hair. Or maybe wearing a pair of doc martens.

      In the meantime, I have my red shoes.

  8. jeannevb says:

    Love the honesty. However, as a woman in her mid 40s with lots of divorced friends, I encourage you to take a closer look at Group B. Try a second date with Mr. Nice… or even a third. Perhaps he’s just putting his best foot forward, or maybe his last girlfriend told him he was a jerk, and he’s trying to change his image. Regardless, nice guys can have something magical hidden behind the pressed shirts and perfect manners. Take the time to unbutton that shirt.

    • Simone Grant says:

      I appreciate the advice. I do. And I’m not lying, I really have tried. Not with him, no. But with others. I’m sure he’s an amazing guy. I wish I knew the right woman to introduce him to. I just don’t think he could ever really understand how I think or why I do the things I do (or did the things I did).

      • Kayle says:

        I think the big difference is that a LOT of people in the nice camp never have been introduced to critical thinking or even the bulk of our other, more “shallow” stuff and certainly not our deeper experiences and perspectives we’ve evolved because of them. Sometimes it makes communicating even on a surface level totally impossible. that’s where they’re fundamentally different and can’t really get us excited. It’s just boring.
        We’re looking for more than just someone to fulfill a role or make us feel loved in an abstract way (to us. because kittens and fluffy bunnies and “nice hugs” and hallmark cards are like mrhuh? to do with who we are). We’re looking for someone who adds something to the experience of life that justifies choosing being paired over being alone. Most people don’t need that or look for it. They would just prefer not to be alone (and appreciate fluffy bunnies kittens and cetera). We would prefer to be alone rather than give up time and energy without feeling it’s reciprocated in a way we can use/appreciate. And also tend to feel that nice guys deserve someone who can appreciate them to.

  9. SecretSquirrel says:

    Have you ever taken a “nice” guy to someplace with an edge to see whether he has that inner tiger that he’s hiding? He may be from group A but so bound up in his current life that he comes across as a group B type. Just a thought.

    • Simone Grant says:

      Oh, I could tell you stories. Hahahahaha. There ARE actually stories I don’t feel comfortable telling on the blog. Maybe eventually.

      Believe me, I’ve known plenty of solid citizens (myself kinda, sorta included back before I left my old career) who wear suits every day but who are clearly in the A camp. It’s not hard to spot them/us. Really it’s not. Back in my post I mentioned my old friends, the now corporate VIPS? My 2 closest friends both have the distinction of getting me/us tossed out of bars. They both are seriously VIPS now. One sits on a lot of corporate boards. But just a couple of years ago we nearly got thrown out of a bar again because she nearly caused a riot. It was hysterical (it was a very posh place and we were all dressed up).

      Like I said, I don’t expect everyone to get it.

  10. Brittany says:

    I think your response about the differences between nice and kind was spot on. I think I understand your dilemma though. I’ve always been in “Group B,” and I tend to gravitate towards that type of guy as well, but the “too nice” syndrome is slippery slope. Those guys, unfortunately, tend to get boring after a while. I obviously don’t want a guy who’s an asshole, but I do want someone who will keep me on my toes.

    • Simone Grant says:

      Glad I could answer that one without sounding trite. I think most of us seek partners who are kind. But “too nice” tends to mean someone who is overly deferential. It doesn’t seem like too much to ask for.

  11. AOC Johnny says:

    Thanks darlin I had a few reasons on my mind what would nice boy entail in this case, I get it and was spot on.

    Compatibility means a lot. How you view the world from your experiences is a big deal.

    Thanks for clarifying


    • Simone Grant says:

      Glad I could help clear that up. There is absolutely nothing wrong with nice/kind/decent guys. I just don’t happen to be a nice girl. And compatibility means a lot, like you said.

  12. Jonathan says:

    Crap. Yeah, I’m a ‘B’ who wishes more and more he were an ‘A’ or at least dabbled in ‘A-ness’. Haha! That came out totally wrong.

    • Simone Grant says:

      No one is completely happy with who they are or how they lived their lives in the past. I, for one, wish I was a little kinder to myself and my body when I was younger. I could use a few of those brain cells back:-)

  13. D says:

    I don’t think this guy is actually a nice as you think. Rather, he was acting nice because he thinks that’s the way to attract women. A lot of guys make this mistake. I used to make that mistake.

    BTW I’m in group B but I was also something of a punk — i.e. one that got good grades — and later became an entrepreneur. There are many rules that can be broken. Some people adhere to social rules while ignoring business rules.

    • Simone Grant says:

      Entirely possible. But with this guy, I don’t think so.

      And, um, breaking business rules doesn’t make you a punk :-) I’m actually laughing very loudly right now. Sorry, but it’s incredibly funny.

  14. Teri says:

    you are right to follow your instincts. if you don’t see a connection with someone, why go out again?

    i often feel judged about my choices as a woman in my mid-30s. people see me turning down someone for a 2nd date and think i’m crazy, because, OMG!!! don’t i want to get married and have kids soon?!!! i would love to get married and have kids, but not with the wrong guy.

    dating can be brutal and you do what you have to do.

    • Simone Grant says:

      First welcome (sorry, if you’ve commented before, I don’t recognize your address) and thank you. Thanks so much of what goes on in my mind. I feel judged, not just here on the blog but IRL about every dating decision I make. What’s wrong with him? Why didn’t that relationship work? Why couldn’t you stick it out a little longer, maybe things could’ve worked out.

      We’re big girls. We’re going to have to live with the decisions we make. We’re smart enough to know that. Let us do what we have to do.

  15. Tahoe Bill says:

    Well hey, you didn’t TELL us you wuz ex-punk. Thought you were just all prissy & stuck-up! 😉

    Seriously, though, it’s NOT horrible to think “I wish I knew the right girl for him” during the date. Actually, I think that is kind. Nothing wrong with meeting someone and introducing them to someone else. In fact, I think dating would be all around better if we did more of that.

    Also, imo you don’t have to have the same background as someone else to get along. What matters is where you are now, not how you got there.

    • Simone Grant says:

      Certainly, there’s no need to have the same background. I agree completely. But I think it’s important to be able to understand one another and how you think/what makes you tick. And sometimes people are just too different.

      I am who I am now, but I’m also how I got here. It’s not that complicated, actually :-)

  16. browolf says:

    Some people want an easy life and some people don’t. I’d surmise you get the most reward from things you have to put effort into. You challenge yourself. Your blog perhaps is a case in point. It’s only natural then you want a guy that also challenges you. Nice guys are just too easy and you’re not going to learn anything about yourself there.

  17. Veronica says:

    How come most of the guys I’ve met (and even been on dates with some) are Group B? Or do guys just claim themselves ‘Group B’ for it seems the most ‘secure’ condition? I’m wondering now…

  18. Black Iris says:

    Here’s the funny thing – the reformed “bad guy” is a huge turn-on for many women. And it seems to me that guys don’t mind settling down with someone who isn’t as wild. The “good girl” admires his nerve. The “bad boy” gets to make her a little wilder. He settles down a little, she feels pleased and proud. So why doesn’t it work in reverse – a guy who never had the nerve to run wild can enjoy being with someone who did, but is now calmer?

  19. Jaclyn says:

    It’s hard to find the right guy especially when you have high standards! I read this article and it opened up my view on what I thought I wanted and what may work best for me. May help!

  20. LushFun says:

    going to quote ya:
    “I’ve tried, really I have, to have relationships with guys in Group B. And it just can’t work. Our brains just work too differently. I challenge everything. I’m always asking WHY.”

    Think of the most bitter thing I could say… and put it in the context of age, opportunity, and actual reality. Choice is elusive here today gone tomorrow, alas it is ignored. People are delusional at times at to what they can achieve.

  21. DakotaGrey says:

    I just read this, and I have to say it’s so true! I like you have a streak of picking the bad ones. There is nothing wrong with Group B and you tell yourself all the time to be with Group B but like you, I just can’t. Your minds don’t sync and after a while (for me a very very short while) 5 get incredbily bored with Group B. I’ve never been that type of ‘good girl’ to sit down and play wifey from the start. Not me will never be me. And the Group A guys play into that bad side. Which unfortunately has its expiration date marked from the start. But none the less I keep going back to the group A puddle…and I have a Psych degree! ha, could never figure that one out.

    What it comes down to for me is the challenge. If a guy is a push over and there’s no challenge to it, im bored, next. Even if they are the sweetest guy. I’m still bored. Group A guys master the challenege and I’m hooked.

    Thank you for sharing your stories! I love them!

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