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

I Made a Girl Cry on the First Date

Today’s guest post is written by Dennis Hong.

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

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

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 “ 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 . 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 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.

Looking for dating advice? Then check out Dennis’s group dating advice site, LemonVibe, where everyone gets rated on the quality of their advice!

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14 to “I Made a Girl Cry on the First Date”

  1. I would think it’s the fact you pretended to be driving to your home (not hers), it probably freaked her out.

    Unfortunately it was probably too early in the relationship to tease her as she really didn’t know you properly.

    Maybe you should mark that down to a ‘lesson learned’.

  2. jamy says:

    I agree with Christine. When Monica backpedaled, if you’d accepted it with good grace instead of a lot of teasing, you might have had a second date. If you could’ve taken it more easily when she decided not to go back to her place instead of pressuring her, even playfully (though I wouldn’t have found it playful), then you might have avoided her emotional reaction. The back and forth banter was her trying to be “cool” and avoid you deciding she was a bitch.

    Why this isn’t perfectly clear to you is what I don’t understand. She changed her mind, you harassed her, she got upset. That’s not very mysterious.

    • Dennis Hong says:

      Meh. I wasn’t really looking for a second date after that.

      • jamy says:

        A second date isn’t the point–you ask at the end of the post, “What was it? I never found out.” I promise you, she felt harassed. I’m not saying you meant to do it but you thought the teasing was fun and playful and she didn’t.

        • Dennis Hong says:

          She changed her mind before I started teasing her. She suggested the movie while we were at the bar, and by the time we got to the car, she’d changed her mind. That was what I was asking about.

          Either way, it was a tongue-in-cheek comment. Obviously, people are allowed to have a change of heart.

          • jamy says:

            But she cried because you teased her, that’s my point.

            • Dennis Hong says:

              Yes, I know that. That was already perfectly clear to me.

              I know I made her cry because of my teasing. Come on, what idiot couldn’t figure that out? My question was, what made her change her mind in the first place? You seemed to take that as me asking what caused her to cry.

              • jamy says:

                Sorry, I got turned around in the story. My apologies.

                What made her change her mind? Probably nothing you did, merely the realization that she wasn’t ready the spend the night with you. Probably not that she didn’t like you. I know things might not have turned to sex, but certainly there was little sleep to be had…and thus the change of heart. At least that’s why I would change my mind in a similar situation.

                • Dennis Hong says:

                  No worries. Yeah, that’s pretty much what I figured. Like I said, everyone’s allowed to have a change of heart.

                  Oh, and for what it’s worth, we had met once before at a friend’s get-together, and the entire night consisted of playful teasing and flirting. That’s why I was kind of taken aback when she started crying all of a sudden….

  3. Jordan says:

    I respectfully disagree with both of you. Teasing is an integral part of flirting, and also a great way to start the flirting process, especially on a first date. The first encounter is as much about “not messing it up” as it is about seeing if you are compatible with that person. If you are a guy who likes to tease, then find a girl who can dish it back.

    Why she freaked out is no mystery, this is where I agree with Jamy. She proposed seeing a movie on a weeknight. Though you made real life turn from a romantic comedy to a sob fest very quickly. She wanted you, but she also wanted to be treated like a lady.

    Was it your intention to get laid….of course. We can play like we are high and mighty beings, but when the food is on the table we are enticed to eat.

    • jamy says:

      You think teasing is great, but not everyone agrees. You are right that if you like it, you should find someone who does. But I’m not sure that teasing someone about changing her mind at midnight on a weeknight on a first date about inviting you home is the way to make anyone like you.

  4. Dazediva says:

    To suggest a movie at 11:30 p.m is a clear sign for ‘I’m into you, I don’t want the night to end’ .. how many cinemas have late shows ? (Sorry folks, am in India right now and the last show is at 11 pm)

    Monica probably realized that by suggesting the movie so late and agreeing to go back to Dennis’s place for a DVD would perhaps make Denis think that she was ‘up for some’. The change of heart came from the realization of this, topped with the past bad experiences of men not calling her back is what made her back off and cry.
    Dazediva recently posted..M for Make the Time & Mix It UpMy Profile

  5. alanc230 says:

    Call me antediluvian, but it bothers me that society has devolved to the point where there is an expectation of having sex on a first date.
    alanc230 recently posted..How to install Prestashop – A complete guide for beginnerMy Profile

  6. Two of Us says:

    Teasing can be fun, but maybe just a comment would have been sufficient. To keep teasing her, she may have felt pressured causing her to freak out. She probably changed her mind once she got in the car since it was late and truly just wanted to go home.
    Two of Us recently posted..Major Signs He Isn’t the OneMy Profile

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