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

There Was a War In My Head

So, as I mentioned earlier in the week, I had another on Monday night.  I’d been looking forward to it for a while. Or, as much as I look forward to any .

I’d met the online weeks ago, but because of the holidays our date got put off until this week. Which was fine with me. There’s something about having a first date right before NYE that seems kinda weird to me.

Anyway, he suggested we meet at Flatiron Lounge, which is one of my favorite places. Not anywhere near where I live, but totally worth traveling to.

I walked in and even though it was surprisingly uncrowded, I couldn’t find him. Not until he waved me over. Because he really didn’t look like his picture.  At all.  He was much less attractive than I thought he’d be. And I didn’t start out thinking he’d be George Clooney.  Just a not bad looking guy. If you know what I mean.

That said, anyone who’s a regular here knows that I have manners. So I sat down and made the best of a potentially situation.  And it wasn’t long before I realized that he was, indeed, one of the coolest, smartest guys I’ve met in ages.

And so started the war.  In my head.  I don’t know if this is a familiar experience for other people, but it’s happened to me many times.  I sat there, having a great conversation and fabulous , while in my head there was an all out war going on.

Side A:  He’s awesome.  This is the best conversation you’ve head in ages. You need to get over yourself and NOT screw this up.

Side B:  Don’t be an idiot. You’re never in a million years going to want to get naked with him.

Back and forth, back and forth. For a couple of hours. The date actually ran longer than I wanted it to while I tried to resolve the conflict (and couldn’t).

And so…  nothing did get resolved.  I doubt I’ll see him again.  I want to be the kind of person who can see past appearances. But I can’t. At least, not in this instance.  Which sucks.  Because he really is an awesome guy.

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33 to “There Was a War In My Head”

  1. Kim says:

    Now I’m dying to know what he looks like, so I know how high your standards are. Haha.

    I think you should go out with him again, because looks can grow on a person, but not necessarily in one sitting. Obviously you know that, but just sayin’.

    If he’s an absolute troll though, I totally get it.

    • Simone Grant says:

      I don’t know how to say this w/o it sounding WRONG, but in general my standards are very flexible. I have no issues re height, race, ethnicity, baldness… I used to HATE facial hair. And then one day I fell in love with a man who had this repulsive beard. And I learned to not hate the beard (and then he shaved the beard, figuring out that I really did hate it).

      I think all kinds of men can be attractive. But. Sometimes there just is no chance. I think this might be one of those times.

  2. Kelly says:

    This happens to me ALL THE TIME. And it really, really sucks.

  3. Nikki says:

    Oh this is one I know well. I think I’ve just accepted I am shallow and appearances-based at this point in my life.

    That being said, I have def been ridiculously attracted to men that were not conventionally good-looking. It was the conversation, etc, that got me – so maybe I’m not as shallow as I think.

    Some people you’re meant to be friends with, some you want something more. I don’t buy the BS about men and women can’t be friends. Maybe this guy is awesome but you’re not feelin it. Friend = check. More than that? You might be wasting your time and his. That said, Kim is right and people can grow on you…

  4. Gina says:

    I’ve had this same problem before. I met a guy who was amazing but he wasn’t exactly good looking. I decided to go on a few dates with him and to my surprise the more I got to know him the more attractive I found him.

    • Simone Grant says:

      I have certainly found myself, at the end of a couple of hours, finding a man attractive who I didn’t think was attractive at the beginning of a date. But it’s never happened after that. I think (but I could be wrong) that a few hours are long enough, for me.

  5. LildevilMama says:

    It’s funny you’re having this dilemma, mostly because I’ve had it about the absolute awesome guy I’m getting to know right now. He’s adorable, but doesn’t meet some of my usual ‘must haves’, and yet his sheer awesomeness has given me reason to overlook that other stuff.

    • Simone Grant says:

      Well, I’ve fallen for men who were the pure physical description of what I usually find GROSS. And I’m still not sure what my Must Haves are beyond empathy, communication skills, kindness (in other words, I don’t have any physical must-haves) and I’m pretty sure I’m not willing to live w/o those AGAIN. But I think it’s awesome that you found someone that works for you.

  6. Kelly says:

    Why analyze so much? I say turn off the chatter in your head, go out with him again, and just roll with it. We spend way too much time wondering if we should put any investment of time into a man which in my opinion wastes opportunity…this is the very beginning, so just roll with it, date him again, and definitely date others too. See what happens. That’s my $.02.

  7. As a man, a horribly gnarled troll-born troglodyte, I find that I can be quite brave when it comes to quality time with the fairer sex, because I am aware of my, let’s say, lacking luster. I know I’ve put aside my fear of being rejected by the Beauty because of my terrible, “my God, what is that thing?” features, so I can walk into any situation with confidence, style and a serene composure. We all enjoy fine company, but don’t date this guy again in the hopes that you will get used to his looks. Enjoy him, or not, for who he is. Be honest, and go where you gotta go, to get what you need. So what if he doesn’t ignite your torch? No one can take any points off of you.

  8. pups4me says:

    My first thought after reading this post is why did he look so much different than his photo…was it taken years ago? Did you feel misled by the photo and a little bit angry that is wasn’t an accurate photo? I know that’s how I feel when this happens to me…I’m certain it happens to everyone once or twice who dates online.
    Sometimes it matters and sometimes it doesn’t…there’s no rhyme or reason to it because it all comes down to chemistry.
    If you think there is a tiny possibility the sparks could fly then I say see him again to find out.
    But if you know in your heart there’s no way it will happen for you, then by all means skip it.
    Being true to yourself doesn’t mean you’re shallow :)

    • Simone Grant says:

      I think it was a combination of it being an old and “flattering” picture. You know, the kind that’s so flattering that is doesn’t really look like him. And yes, I do feel a bit misled (and annoyed) by those.

      I agree, being true to myself doesn’t mean I’m shallow. Hell, I could date pretty boys if I wanted to. I DON’T. But looks do matter.

  9. Sexy Sue says:

    You need to have a few more drinks, then he won’t look so bad… and why do you, as a woman, have to be as shallow as a man and be all about the looks? You’re 40+… time to not be so picky… if he’s a great guy, and he’s got a decent bank account to enhance that, I wouldn’t worry so much about the looks. When it comes down to it, you want a good guy who will be there for you in your old age, and who will support you, because God knows, writers rarely make a good living, and women tend not to either unless they’re Oprah or Ellen or Martha. Looks fade… you think you’re going to be the same hot chick in 10-15 years? Even with Pilates and lipo, gravity and time are going to win. If you think he’s so great, then you should go on another date… if he’s hideous, that’s another story… but beauty is not skin deep… anybody can be beautiful on the outside… thanks to plastic surgery… it’s the inner beauty that counts.

    • Simone Grant says:

      Sorry, Sexy Sue, I’m not much of a drinker. So let me ask, at what age would it be appropriate for me have some standards?


      Such ridiculousness. Beauty and attraction is a complex thing, but anyone who pretends that externals don’t matter, for women as well as men, is just a fool.

  10. Jen says:

    For what it’s worth, I’d go on one more date and see if you still feel the same. After that you’ll know for sure. Unless of course you have so many options and dates lined up that you don’t have the time to 😉

    • Simone Grant says:

      Truth is, I’d rather not go on a date if I’m fairly certain there’s no chance I want a relationship with a guy. I’d rather stay home and read a book. Call me crazy.

  11. datehater says:

    I have a two pronged answer/response as this is happened a few times to me.
    1. Go with your gut…if you’re not feeling it now it aint gonna happen. Not that you need to want to jump every date within the first 5 minutes, there still needs to be be some attraction. If you don’t have it after a few cocktails and a good convo, it’s not there.
    2. Go out one more time. Surprisingly enough, when you have some time off to think and digest you will come into the second date with a much clearer perspective.**

    **on a personal note, when i HAVE gone on a second date with “questionable” dates, I have known within the first thirty seconds I was soooo not into it. Which brings us back to point 1……however eliminates any “what ifs”

  12. HP says:

    I’ve so been there. I talked with a guy for a good 3 weeks without ever seeing his picture. We would chat for hours, I’m talking like 10 hours some night, we had many of the same interests and it was so easy to talk to each other. Though it took him forever to send me a picture. We finally got our schedules together to have a simple coffee date and I was able to convince him to send me a picture. I was nervous because I knew he’d either be really good looking (and I had hit the dating jackpot) or he wouldn’t be my type. Well to be perfectly honest I was shocked at the picture that I received, and not in a good way. Being the polite person that I am I met him the next day in hopes that it was just a weird camera angle and he looked better in person, well unfortunately I was wrong and he looked even worse in person. Now I’ll admit I’m shallow but I’ve found non-traditionally handsome men very attractive because of their personalities. But he was, to be totally honest, freak show ugly. It was the longest hour I’ve spent and I almost felt a little bit like it was some cosmic joke. I sent him a polite email a few days later that I didn’t think we meshed well in person and that was that. Now I will never go out with someone unless I see a picture first. Call me shallow but to a point looks do matter.

  13. DD says:

    Do not ever listen to people like Sexy Sue.
    You haven’t lowered your standards this long, why start now.

  14. heather says:

    Hey! I think sexy sue does have a point. Simone is 40, being dating for years…I for one am interested just why excatly not one of the 100s of men Simone has dated has not worked out. But you know, if she was in a healthy, established relationship, who would read her blog then?

    • Simone Grant says:

      Yes, because the fact that none of my prior relationships have worked out/I’ve chosen to not to stay in bad relationships is a sure sign that I’m shallow and impossible to please. Or maybe this is just where I’m supposed to be in my life. Nah, couldn’t be. I must be shallow.

  15. DD says:

    Duh, It’s so much better to cling to anyone who is willing to be with you then god-forbid be single after 30.
    sheesh some of the sentiment I’ve heard from women over the years…it seems they don’t care who they are married to, as long as they are married.
    Also, if you were going to lower your standards it would probably have to start with your city-suburb standard, instead of looks haha. (I love your blog btw).

    Some people find their soul-mate at 20 while others have to wait a bit longer. Keep on doing what your doing Simone.
    If you wanted to just simply have a boyfriend I’m sure you could at the snap at a hat. But from the tone of the posts I’ve read, your holding out for something much bigger and better than that.

  16. Arlene says:

    Its been said before, but I am going to say it again – since he is so awesome, I would give it another go. Maybe he is having a bad hair day? worst comes to worst, you have another great conversation, stimulate your brain again, and walk away knowing for sure, that he was not the one for you.

  17. Rain says:

    I believe in the “click” honestly if there was no physical click then there is nothing that you can do…..sometimes the guy doesnt have to be good looking but there is this crazy chemistry that he emits where do start to see a sexiness to him.
    So if it dont click…it simply dont click…

    I am enjoying reading your posts very much…

  18. LJ Maggie says:


    I love your blog and dating adventures. I will admit going on a first date and not being attracted to the guy but we stayed friends and later I was attracted to him. (2 years after knowing each other his true colors came out and not in a good way. We are no longer friends.) That experience taught me to get to know someone. I did go on a number of awful dates and now have started dating someone that is nice and good looking. It took tons of first dates to get to this point.

    I think as you get older your standards change in what you are looking for in a partner and there is nothing wrong with that. And for some of us we have to go through a lot of frogs to find our prince.

    Don’t listen to the Sexy Sues of the world that say because you are over 40 you should find someone that has a bank account and that you shouldn’t worry about his looks. There should be some attraction there.

    One my small biz owner clients is a dating and relationship coach for women over 40 and she tells her clients that the first date is usually a meet date. If you aren’t sure, go on a second date and after that if you still don’t feel it, then politely let him down.

  19. Look Simone,

    Looks and attraction are important & anyone who says they aren’t is either lying or ugly!!!! That being said looks are very subjective. What one woman finds subjective another finds repulsive. I don’t ever think we’ll ever know the reasons why one woman finds Tom Cruise “HOT” and another woman thinks he’s a lil troll.

    If you can not seeing u’rslef getting naked with this guy (your words) how could you be in a relationship with him. This doesn’t make u wrong it makes you honest. Physical attraction is merely one piece of the puzzle. However if it is missing the puzzle will be incomplete.

    When I first met my wife she was “OK”. At the time I was also dating a ex-flight attendant who was beautiful & had an incredible figure. But the more I met my wife the more I realized that she was the one. Why? B/c she had all of the things I was looking for, including physical attraction.

    So, if u are not attracted to a guy and u are not a shallow woman who only dates guys w/washboard abs & perfect teeth I suggest u simply move on. Don’t waste his time & don’t waste yours.

    Good Luck. The right Guy is out there 4 u. It’s just a matter of finding him.


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