Check Your Baggage, Please

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If you had to sum up your worst date ever in one sentence, what would it be?

Here’s mine: I made a girl cry on the first date.

How does one accomplish this exhilarating feat, you ask? Let me tells ya….

My first date with “Monica” was actually one of the most fun dates I’d ever been on (well, up to the point where I made her cry). We had met through a mutual friend, and when I called her a few days later, we chatted for almost an hour before we decided that we might as well go out to dinner. After dinner, we headed to a local bar, where we laughed over cocktails for several more hours. I felt like I could talk to her all night, and she seemed to feel the same way.

Towards the end of the evening, she put her arm around me, furrowed her eyebrows pensively, then asked, “do you wanna go see a movie or something?”

Seeing as how it was 11:30 PM on a Tuesday night, I responded that it was probably too late to see a movie, but we could watch a DVD back at my place. She liked the idea, so we headed out.

Once we got in my car, though, she had a change of heart.

“You know what? It’s getting kind of late. Maybe you should just take me home.”

“Aw, really?”

Not wanting to reveal the disappointment in my voice, I instead launched into “smart-ass mode.” This is where I cleverly and charmingly rebutted every reason she had for calling it a night. (Okay, fine. In my mind, at least, I was being clever and charming.)

“Ya know, I have to be at work before you even have to be awake tomorrow morning.”

“Oh, come on. You’re sounding like a chick. I thought you said you weren’t the ‘chickish’ type.”

“Never underestimate the power of caffeine!”

As we bantered back and forth, she was smiling the entire time. So, she seemed to be enjoying herself. Besides, I figured she’d notice that I was driving back to her place, not mine. And so, I continued the playful—or so I thought—ribbing.

All of a sudden, she burst into tears.

“Why does it always end up like this? Why can’t a guy just drop me off and kiss me and say goodnight? If we go back to your place, you know we’re not gonna watch the movie. We’re gonna be messing around all night, and before we know it, it’ll be six o’clock in the morning, I won’t have gotten any sleep, and I’ll be completely useless at work!”

Whoa. This was definitely not the reaction I was hoping my charm would elicit. Regroup! Regroup!

Inside my mental huddle, I went through a quick checklist:

Did I have fun tonight? Absolutely.


Do I want to continue hanging out with her? Certainly.


Am I hoping to “get some”? Umm… okay, sure. But, honestly, I only suggested coming back to my place because she wanted to see a movie at 11:30 PM on a weeknight.


Okay, so did I come on too strong? Hmm. I don’t think so. Dude, what the hell just happened?!?

Still bewildered, I unleashed a torrent of backpedaling, dousing every accusation she made with some variety of, “I’m sorry, that’s not what I meant.”

That seemed to calm her down somewhat. Between sobs, she eventually admitted that she always seemed to date guys who would hook up with her and never call again.

Great. I guess this means I have to be her friend tonight.

I did my best to convince Monica that I actually liked her and just didn’t want the night to end. Finally, she stopped crying. At that moment, though, a new thought spring into my head.

Hey, wait a minute! Was it fair of her to assume that I was just trying to get laid?

My sympathy erupted into frustration. And boy, did I give her several pieces of my mind.

“Fine! I get that you thought I was just trying to hook up with you. And… okay, maybe I did want to. But, I only suggested coming back to my place because YOU wanted to see a movie at 11:30 on a weeknight. You had NO right to judge me the way you did just because you’ve dated a bunch of a-holes in the past!”

Somewhat to my surprise, she understood and actually apologized, admitting that she really liked me, too, and maybe that’s why she got so emotional. By this time, we’d been parked in her driveway for half an hour, so I gave her a peck on the cheek and dropped her off. She thanked me and said she’d call me.

Well, she did call, and we did talk on the phone a few times after that. But we never went out again. I guess we both just lost interest. I mean, how could we ever top the epic fail that was our first date?

Since then, I’ve learned to laugh about that night. After all, how many people can claim that they made someone cry on the first date? If nothing else, it was a lesson on how the emotional baggage we carry can sabotage new relationships. I also learned to save the smart-assery (smart-assity? smart-assinine?) for… well, maybe the second date.

Still, it wasn’t until a year later that what should have been the lesson of the night struck me. Yes, Monica assumed that I just wanted to sleep with her. And yes, it was a horrible misunderstanding. But wait….

She accepted at first!

So what happened between the time we left the bar and the time we got in my car that made her change her mind? That’s where I messed up!

So what was it? I never found out. I was too wrapped up in the fact that I made a girl cry on the first date.

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By day, I'm a marriage and family therapist. By night, I am a relationships and comedy writer, which can be redundant or an oxymoron, depending on your perspective. I'm the creator of Social Savvy Sage, a coaching service that focuses on developing social skills. I am also the creator of Musings, the blog you're reading right now. You can find me on Twitter. (I am not the creator of Twitter.)


  • This sounds duplicitous to me.

    That’s called being honest with myself. It’s a good thing to do, and it doesn’t make someone duplicitous.

    Incidentally, why are you so fixated on this? Why is it so necessary for you to lecture me on how I supposedly misbehaved? Is it to satisfy some innate issue with self-worth?

    Maybe you should think about that before you keep doling out the misguided advice….

  • Hi Dennis,

    I looked at the story again and I dont see where my false assumptions are. You said to “Read the story again. Pick up everything happened between 1 and 2.” I read this but am still not understanding where the assumptions are. Could you please explain more?

    I chose to respond to your article because you asked a rhetorical question in the last paragraph implying you were/are still processing the event and since this is a blog which allows comments to me implies that you were asking for feedback to help you answer your rhetorical question. I was providing my feedback, though not directly to you, but for all guys who read this article.


  • “What you can’t seem to get is that I didn’t give her a “piece of my mind” because I was disappointed. You keep jumping from 1) her changing her mind to 2) me giving her a piece of mine.”

    I do understand. You stated that you gave her a piece of your mind because your empathy erupted in frustration because you thought that she assumed you were just trying to get laid and you thought this was an unfair assumption. I only thought your disappointment was part of the event. (though you did say immediately after she told you she changed her mind about coming to your place the following “Not wanting to reveal the disappointment in my voice,”…).

    From what you wrote, it sounds to me that she didnt completely think you were trying to get laid, but that it was somewhere in your thoughts and she felt uncomfortable by it. I would say she was likely right given that you said “Am I hoping to “get some”? Umm… okay, sure. But, honestly, I only suggested coming back to my place because she wanted to see a movie at 11:30 PM on a weeknight.”

    To me, this reads like you were open to the possibility of fooling around with her though couched it _technically_ as “watching a movie.”

    To me, what Monica wants is for a guy to be clear that he’s not looking to fool around on a first date.


  • Okay, sure. I was trying to be tactful about this, but since you keep pressing the issue, I’ll spell it out for you.

    Here’s your problem: you pop onto a random blog, you have no idea who the people you’re interacting with are, you have no clue what actually happened, and then you actually have the audacity to dole out misguided advice.

    Let’s take a look at your posts on this thread, why don’t we?

    You say that I lost my cool because I was disappointed that I wasn’t going to get any.

    WRONG. I lost my cool because she made an unreasonable judgment about me. That conversation had nothing to do with her changing her mind. As I noted in the article, we were already at her place by the time all this went down.

    You say that she didn’t get back to me because I gave her a piece of my mind.

    WRONG. As a matter of fact, she did, also as noted in the article. Read, dude, read.

    You say that a guy should “lead.”

    WRONG. It’s not 1950 anymore, and that attitude only reveals your chauvinism. Women want a guy who’s assertive and honest, not someone who’s going to “lead” them.

    Three strikes, buddy. You’re outta there. Oh wait, here’s one more:

    You say that I was wrong to give her a piece of my mind.

    WRONG. Given the circumstances, we were way past the typical first-date posturing. At that point, what she needed was a swift kick in the ass for overreacting. And she appreciated it.

    There’s quite a few more. But I hope you’re starting to realize how wrong you’ve been through this whole interaction.

    For the record, I can admit when I’m wrong. I know how to reflect on my actions and figure out where I messed up. In this case, where I messed up was being an unrelenting smart-ass. Oh, but look at that? Of all the feedback that you tried to dish out, this little tidnit of insight was not amongst them.

    So, you missed the one glaring piece of advice that would’ve been helpful. And, instead, you fixate on several other pieces of useless feedback. Great job, dude.

    And now, I’m going to give you some free unsolicited advice, because you seem to fancy yourself quite the dating coach. But just this one time. I usually charge for this shit, so if you make me have to school you again, expect to get a bill from me.

    I’ve checked out your blogs. I can tell that you’re a smart dude on other topics, but you’ve got a lot to learn when it comes to dating and relationships. Trust me, I have way more experience than you on this. I know how to treat women, I know how to interact with them.

    From your advice, clearly you don’t.

    Relationshisp aren’t about hard-and-fast rules. Relationshisp are about adaptability and flexibility. I think I read that on one of your own posts, ironically enough. Well, guess what? When you start going around dictating to people how they should or should not behave, when you start saying that “this” is the right way to go about it, and “that” is the wrong way, then you’re the one who’s WRONG. (That word starting to sound familiar to you?)

    Because, believe me, you DON’T have all the answers. No one does. And when you get that through your head, when you lay off the blanket statements and absolutist advice, maybe you can start enjoying love and life for the mysterious journey that it is.

    Finally, here are some tips on effectively coaching people:

    1. Don’t offer unsolicited advice. Don’t.

    2. Before you start leveling judgments, ask questions and clarify. Be sure you actually KNOW what happened before you start offering your feedback.

    3. Offer useful and insightful feedback. In other words, give good advice.

    Guess what, dude? You’ve done none of these.

    So, why don’t you go back to the book that you’re reading and keep sharing your stories? There’s nothing wrong with that. But, lay off the attempts at coaching people on their dating, because you 1) have no clue what you’re talking about, and 2) have no clue how to effectively provide feedback to people.

    But good luck, though. And if you really do want to learn something about dating and relationshisp… that’s what we’re here for.

    Thanks for reading.

  • Hi Dennis,

    I was actually trying to be nice with my inquisition. Id just like to engage in a discussion. You’ve really run this discussion into a corner and Im not sure what to say now.

    Im happy if you disagree with my advice. I did ask you some questions and offered some conjectures and welcomed you to clarify them but you didnt really answer any of them until this post.

    Thanks for your last response, and I disagree with much of what you wrote. Im not saying the events you experienced didn’t happen, but I dont believe your assessment of the situation is congruent with what you wrote. I think a different point of view would have better served you and Monica.

    I dont think anyone deserves a “kick in the ass” (your words) on a first date. I think on a first date people should be quick to listen, slow to speak, and slow to anger.

    Thanks for your compliments about my blog. Im still working through this as I will be for the rest of my life.


  • Read your first comment again. How “nice” were you? How “inquisitive” were you?

    It was all lecture. You left no room for “discussion.”

    And if you thought you did… again, that’s just shitty coaching.

    And there’s your kick in the ass.

  • Hi Dennis,

    Im not sure how to quantify niceness and inquisitiveness. I thought it was pretty nice though (whatever that means I guess). I offered some conjectures and suggestions to you (via words such as ‘likely,’ ‘would try’, and ‘wouldve been better’).

    I would say the strongest statement (in the sense that I imagine some people project it onto themselves personally) I said was “No girl on a FIRST date EVER should be talked to like that.” I suppose I could have been a little softer here. Apologies.

    There was obviously was lots of room for discussion or we wouldn’t be here half a dozen posts later.

    “It was all lecture. You left no room for “discussion.”
    And if you thought you did… again, that’s just shitty coaching.”

    This statement makes no sense to me.

    “And there’s your kick in the ass.”

    Sorry, Im not really into S&M.


  • This statement makes no sense to me.

    And that’s probably why you shouldn’t be going around the internet, trying to tell people what to do.

  • Hi Dennis,

    Im sorry to keeping asking this of you, but your last response doesn’t address my concern, can you please address my comments directly.

    Also, I want to let you know that you dont have to read everything or enjoy everything that I post.


  • I’m not going to waste my time trying to teach you how to give feedback and engage in helpful discussion, as you claim you’ve been trying to do. Buy a book.

    If you post something on my blog, you can bet I’m gonna read it.

  • Hi Dennis,

    Yes, it seems very reasonable that you would want to read the comments on your blog articles, but you are free to ignore or not respond to any comments I write.


  • Just as you’re free to keep your erroneous opinions to yourself.

  • Hi Dennis,

    I try, generally, to form my opinions from facts I observe (from experience, reading, and other people’s stories mostly). I believe my opinions here to be truthful.


  • Hi Dennis,

    Thanks for your opinion.


  • Okay, I’ve got some time, so let’s do this. Here are all the false assumptions, misguided judgments, and just plain egregious errors you made:

    Dude, you dont take a girl back to his place at 11:30pm on a worknight on a FIRST DATE. Sorry man.

    Wrong. As we’ve discussed, this is not always the case. Besides, absolute statements are rarely correct.

    It sounds like Monica has good boundaries.

    Wrong. How would you even presume to know? You know nothing about her except for what I wrote.

    The guy is supposed to lead and you lead by doing the right thing.

    Wrong. Chauvinist.

    Monica didnt get back to you likely because you talked to her like this….

    Wrong. She did get back to me, as mentioned in the article.

    No girl on a FIRST date EVER should be talked to like that.

    Wrong. Another absolutism. In any case, I know you think you’re being chivalrous, but you’re actually only revealing your own sexism. Women are not dainty objects to be tiptoed around and baby-talked to. It’s perfectly okay to assert your own needs and speak strong words to a woman, as long as you’re not being verbally abusive. I was not. None of my statements, harsh as they were, fall within the realm of verbal abuse.

    It sounds to me like you were disappointed you had no chance to “score” and then took it out on her.

    Wrong. How presumptuous of you.

    I didnt know it was okay to speak so strongly to a girl on a first date who decides to change her mind regarding the course of where she wishes the night to go.

    Wrong. I didn’t speak strongly to her because she changed her mind.

    You seem angry.

    Wrong. Just puzzled by how dense you’re turning out to be.

    I now think that it was wrong for Monica to apologize to you. She did nothing wrong. She changed her mind and she has the right to do that.

    Wrong. AGAIN, that’s not why I “gave her a piece of my mind.” I may have been a smart-ass, but she overreacted. In any case, she didn’t apologize for changing her mind. She apologized for overreacting.

    Then, she takes two steps backwards. (and you giving her a piece of your mind doesnt help her.)

    Wrong. It actually did help here see why she was being irrational. She understood. Why can’t you?

    Thanks for your last response, and I disagree with much of what you wrote.

    And you have a right to be wrong. 🙂

    Wanna keep going?

  • Hi Dennis,

    Thanks for your detailed response. I disagree with much of what you wrote.


  • Not to jump into the middle of a wicked fight, but Micah I found the following paragraph to be quite presumptuous:

    **Imagine if you were in her shoes. Here’s a girl who simply wants to go out on a date, have a nice time with a good guy, and then be dropped off at home with a soft peck on the cheek. Shes likely nervous on the date and is wondering about your intentions. She mentions about watching a movie later as she maybe desires to be sexual with you. Then, she realizes this likely isnt a good idea for her based on past mistakes she made and then changes her mind (which we are allowed to do). Next, you confront her in a teasing way about changing her mind (which shes likely heard before) and then breaks down because dating is hard and shes frustrated. She wants a different dating experience and isnt finding it and is thus frustrated. SO, shes confused (and allowed to be). Then, you give her a “piece of your mind.”**

    How do you know what she wanted or was thinking? It’s extremely naive to think that all women are innocent, naive virgins with no motives or desires.

    And since when are people on a FIRST date obligated or even expected to be a shoulder to cry on because of bad past relationship experiences? We’ve all got baggage, and if we were to dump it all out on the table on a first date, we’d never get to the second ones.

    And by the way, “The guy is supposed to lead and you lead by doing the right thing.”

    Are you kidding me? Maybe after he totes me around like a little trophy wife he can give me my monthly allowance to buy groceries and have my hair fixed every now and then. After all, I want to look good for my man, not myself!

    Get a clue.

  • FatalFlyingGuillotine

    I really don’t like feeding a troll because it metabolizes attention and excretes shame and stupidity during their sad existence but I’ll make an exception:

    Micah claims he forms his opinions by observing the facts. The FACT is that Micah should turn whatever stunted reading comprehension skills it may have on to its own posts and see what a chauvinistic moron it is.

    Off with its head- this thing and its simplistic, moronic posts are examples of the weakest trolling I’ve seen in a while. Congrats, Micah- you fail at the Internetz!


  • @Micah: You are, of course, welcome to disagree with my statements. Nonetheless, most of these rebuttals had to do with my own thoughts and actions, as well as those of Monica’s. I find it laughable that you claim to know more about my thoughts and actions (and Monica’s, for that matter) than I myself do. Now THAT’s presumptious. But hey, it’s your right.

    @FFG: The sad thing is, I don’t think Micah is a troll. I believe he genuinely believes what he writes. And that, to me, is just sad at this point.

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