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

Anatomy of a Bad Date

Anatomy of a Bad Date online dating dating update  iStock 000010266210XSmallI’ve been a little too overwhelmed with my life lately to keep up with my online dating stuff.  I know that someday soon I’m going to have to schedule a few hours to sit down and clear out the inboxes (Chemistry, especially, will take a lot of time). I’m not complaining.  It’s part of the process.

I have been keeping up with my 2 dates a week schedule and a couple of days ago I took a couple of hours out of very busy afternoon to meet a who I thought seemed very promising.

Boy was I wrong.

I am not, as most people who know me IRL can attest to, untalkative (hmm, that’s not a word).  I’m easy to engage in conversation.  If someone is talking about something I find even vaguely interesting, I’ll dive in.  I didn’t speak much during this date. I couldn’t. First off, this guy was boring the shit out of me.

Recently, my good twitter friend Terry Simpson said something about how talking about one’s self was the least interesting thing to talk about on a date. I’m not so sure about that.  I think the least interesting thing to talk about on a date is online dating.  Followed by a full-scale baggage share.  Seriously, he spent huge chunks of time talking about how his online dating profile was so amazing and he was so great at online dating (which I found hysterical for SO MANY reasons, the biggest one being that he was an old picture guy with bad people skills and it doesn’t matter what you put online if no one is going to want a with you). Then when he got tired of that topic (I barely said a word, no I’m not joking, we were taking a walk on a sunny day and so I tried to tune him out) he started to whine about his recent divorce and job loss.

Eventually, I got tired of listening to him blather on about things and tried to jump in.  I can’t remember what I could have possibly said.  All I can remember is that every time I said anything he cut me off and said, “that reminds me of..” and then mentioned a book by either a philosopher or obscure artist.  And then he went on to lecture for about 5 minutes as to the significance of that philosopher or artist and why they are so under-appreciated.

Why I stuck around so long, I have no idea?  Your guess is as good as mine.  It was a nice day and I was happy to be outside. But I really can’t think of any worse formula for a date:  be an old picture guy (I’m guessing the pics were at least 3 years old, maybe older) + talk endlessly about yourself + shut down all attempts the other person makes to join the conversation with pompous rubbish.

Now, to be kind, the guy is clearly insecure.  I get that.  Old pictures are not a sign of someone who feels good about themselves.  And I don’t think he’s even vaguely aware of how he’s acting.  There was a ‘thank you’ email waiting for me when I got home that night (I had plans immediately following the date).  That doesn’t change the fact that it was one of the worst dates I’ve been on in the last few years.  Years.


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27 to “Anatomy of a Bad Date”


  1. LuckyBroad says:

    I actually once went on a date with a guy who didn’t ask me ONE question. Not ONE. There was zero exchange, zero interest in learning anything about ME, and zero opportunity to actually engage. I think he viewed it as a “if you want to tell me something about yourself, you’ll tell me”. This is only true for so much.

  2. Larissa says:

    Did you talk to this guy on the phone before meeting him for the first time in person? I was just wondering because I have found that after having that first phone conversation with someone I can determine whether or not I want to bother meeting them in person. This has actually kept me from meeting a couple of guys in person, if they are boring me to dead on the phone imagine what that would be in person! I am kind of a newbie to the online dating world and I wrote a couple of posts on my blog (www.larissainnyc.com) about my experiences so far which have been not bad at all.

    • Simone Grant says:

      I did. Sometimes I do and sometimes I don’t. As someone who’s been on literally hundreds of dates with guys I’ve met online over the past decade I can honestly say that I don’t think that phone chats are any more an effective means of screening than a few emails. Some people just give good phone.

      And, um, of my hundreds of dates from online dating only a small proportion have been bad.

  3. kiwicat says:

    I’m sorry to hear about your date. I used to have a friend who was like this: always going on incessantly about the minutest (and boring!) details in his life and never bothering to ask me about what was going on in my life. And when I did mention interesting things I’d done (like taking a course with a Supreme Court Justice and traveling abroad – things that most ordinary people would be curious about), he would only ask me one cursory question and then go back to his own life. Not to mention he was also a failed writer and constantly complaining about how the media and publishing industries fall over their feet over the hottest young writers and how these people would be forgotten in a few years. A valid argument, but when it’s repeated three, five, ten times with nothing new, it just sounds like bitter insecure ranting. Finally, after two years of being friends with him, I’d had enough and dropped all contact with him.

    • Simone Grant says:

      I’m sorry, that must have been hard. I can think of a few friends I’ve cut off ties with over the years and even when I knew it was the right thing to do, it’s always hard.

  4. Lifebeginsat30ty says:

    3 strikes! Geez, self-absorbed much? (him) dodged a bullet there. At least it was only a few hours and you weren’t stuck over a meal! Ugh, your bad date just left an icky taste in my mouth. I really wish we could rate people after these dates.

    • Simone Grant says:

      There are several sites that let you “rate your dates”, but I don’t really get into all of that. I would love to sit around with a few veterans of the NYC online dating scene and dish about some of the guys out there, though…

  5. Steve says:

    Agree with Larissa about talking on the phone first.

    You can weed out twenty or more prattlers, princesses and porkers in the same time you would have wasted on a single in-person dead end.

    Plus, my 1st date poke rate has risen above 85% thanks to that simple technique.

    Let’s take a moment to honor the Great Graham Bell!

  6. Alex says:

    Wow… First off, I’m sorry about this date. Bad dates, for me, just let the air out of my sails.

    You know, it seems to me such an easy thing to NOT go on and on about myself. Maybe this guy was really just nervous or the recent recipient of a lobotomy? I don’t know, but he sounds like a “catch.” =)

    Is there a nice way to tell a person “you know, um, NO, I’m not feeling this date. Bye.”

    • Simone Grant says:

      I’ve ALWAYS wanted to do that – just say “I’m not feeling this, bye”. But I can’t. I want to, but inherently I believe that it’s better to be polite.

      I do know people who claim they’ve done it, after only a few minutes. I can’t imagine.

  7. Patricia R. says:

    I ususally try to do something non-interactive on a first date i.e. a movie. If its an awful date, you can walk away after. If it was good, then scheduling a second date is pretty easy to do. Sitting across from on another over moderately-priced coffee feels like an interview, there is pressure to impress. Trying to hard is called trying too hard for a reason…it’s too hard to deal with.

    • Simone Grant says:

      I’m the opposite. The point of a first date, for me, is to talk with someone. I want to interact. Let it feel like an interview, let it be awkward. Then I’ll know.

  8. Bad dates what a subject. I would love to see a good list of creative ways to get out of a bad date. Because sometimes you know within minutes that it just is not going to work. Then it is just a nightmare going through the motions for a couple of hours with someone you want to smack.

    Actually thinking about it, you could always just say ‘sorry this is not going to work for us, so lets just quit while ahead’.

    • Simone Grant says:

      I’m not sure about that knowing within a few minutes. I’ve had a few dates that needed some time to warm up. I have a theory – some guys are great daters but I would want to have relationships with them (anymore, learned my lesson). Some guys are lousy daters, but maybe some of them are keepers?

  9. This is such a great post because it points out one of the most easy to avoid, but most commonly made mistakes of dating. Any experienced, remotely sensitive human being can probably tell you that a huge no-no in the dating world is to clutter your first date conversation with stories about yourself.

    Of course, the first date is the time to start sharing about your life, but NOT just your life. Ask about the other person. You’re going on a date. Why? To hear yourself talk? No! To find out about the person sitting across from you at the dinner table.

    There is nothing more disappointing than a long dinner date that bores you with stories of his now-irrelevant high school football glory days and doesn’t even bother to ask what you do for a living.

  10. Jolene says:

    Ouch. that sounds like an awful date! The whole blathering on about how great he is at online dating…really? I mean, really. And the old pics – bad, bad move. Kudos for you for getting through it and being nice about it, too.

  11. singlegirlie says:

    Yuck. You know, I go on dates like this all the time. Well, the kind where the guy talks about himself a lot and doesn’t ask me anything. Then there was ONE date who bombarded me with question after question, which was rather disarming as well. Conversation is a two-way street – you give a little and you take a little. I honestly don’t understand why this is such a difficult concept for some people to grab. At least it was a nice day outside!

  12. It is funny how guys meet for the first time and chat to you like you like they are reading from a script and have no real interest in the answers

  13. Tina T says:

    Sorry to hear about your date, but a bad date story makes such a better story than a good date story. You would think that by a certain age people would realize that it’s a monologue, not a conversation if you don’t let the other person speak.

  14. Simone Grant says:

    Thanks – but I’ve always said, I’m not in this for the stories :-) I’d so much rather have a good date and a lousy story!

  15. LadyD says:

    I live in Seattle and keep meeting (as I’ve now deemed them) the “Microsoft Mumblers”, i.e., guys who barely talk (yet write emails that are extremely articulate, interesting, etc.), and I end up asking all the questions and getting basically monosyllabic answers in response – AAAGGGHH!! I’m so tired of being the “entertainment”; I work for lawyers and have for many years, so I’m used to working with usually rather loquacious, intelligent people. But some of these Microsoft guys are just so frustrating! Good guys, intelligent, have their sh*t together, etc., but just DO. NOT. SPEAK!! I have now changed my Match.com ad to state: EXTROVERT WANTED. *sigh* I hope this helps!