Discuss: First Date Mistakes

Aug 17, 2012

A few nights ago, I made the decision to remove my laptop from its permanent home next to my reading chair, and carry it to a too-cool-for-school coffee shop near my apartment.  I thought a change of scenery might do me, and my productivity level, some good.  

I was sipping a chai tea latte and enjoying some harmless people watching, when a young couple who were clearly on a first date sat down next to me.  They started off with the usual banter about their jobs, their roommates, how they like/hate D.C..  The date seemed to be going really well, until they ended up talking about their favorite things (movies, restaurants, etc.).

The Great Gatsby is my FAVORITE book. I’ve read it probably one hundred times,” the woman said with a flourish.  

“I haven’t read that since highschool,” the man replied, “who was your favorite character?”

“Probably the guy with the house,” she said.

There was a pause in the previously free-flowing conversation.  

The change in the air was instant and palpable.  Where there had once been electricity, there was now stagnation.  Watching them over the top of my computer screen, I could see the man’s mind working.  “The guy with the house?  Does she mean Gatsby…the title freaking character?”  He took a long sip from his cup, and shifted in his seat.

“Well, what was it you liked about the book?”  His tone was suddenly tentative, like a man walking through a minefield.  

“The clothes,” she responded.  

The date continued on, but the magic had clearly died.  By the end, the two of them were sucking down their previously sipped drinks trying to get to the end of the date faster.  It was sort of sad to watch their date go from promising to painful in such a short span of time.

Now, I don’t know this woman, and I certainly don’t know if she’s read The Great Gatsby 100 times, let alone once.  But if she was pretending it was her favorite book to sound smarter or well-read, she needn’t have bothered.  The guy was really into her until he got the sense that she was faking it.  

I wonder what would’ve happened if she’d said Twilight or Hunger Games?  Maybe he would have judged her, or maybe he would have found her honesty refreshing.  The world will never know.

Witnessing this incident got me thinking about the biggest mistake that I’ve ever made on a first date.  I thought about it for nearly an hour, and couldn’t think of any particularly troublesome behavior.  Then, on my walk home, it hit me.  The biggest mistake I ever made didn’t happen on the first date itself, it happened immediately after.

I’d gone to a nice bar for a drink with a man that I’d met through work.  We had a good conversation. We shared a few laughs. And as I climbed in a cab to go home, I thought, “Wow. That was a pretty good date.”  

So there I was, sitting in the back of a cab, driving past the Capitol, when I was suddenly hit with this deep feeling of loneliness.  Moments before, I’d been thinking about what a great guy my date was and hoping I’d see him again.  Then, in an instant, my post-date buzz was hijacked.  It was like I took the souffle from the oven to soon and watched it deflate before my eyes.  

I couldn’t shake the feeling, and so I did what I used to do when I got lonely: I text messaged my ex “just to say hi.”  Like we were ever capable of a simple “Hello.”  You can imagine how healthy that conversation was.

The guy called the next day, and we went on two more dates, but the spark had been snuffed out.  The connection was gone.  What was new and unspoiled felt tainted somehow by my shame, and I just couldn’t recapture that first date magic.

So let this be a lesson to you all, when you have a nice date with someone, revel in it for a minute.  Don’t get lonely and dial your ex-boyfriend or go back to your apartment and start Googling baby names for your future children.  Just take a breath, and bask in the glow of a nice first date.  

So what’s the worst mistake that you’ve ever made on a first date?


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  1. becca says:

    “bask in the glow of a nice first date.” Love it and so hard to forget. Recently I found myself planning out my fall, engagement, wedding, life with a guy I went on one date with instead of just enjoying the memory of my best First Date to date.
    Happy weekend!

  2. LeighB. says:

    My worst mistake was shortly after I got out of a long term relationship and I was afraid of being along and single. I went out on a date with the first guy who asked me (kinda a set up by some friends) and I knew it wasn't going to work 30 minutes into drinks and tapas but he was perfect on paper and I didn't want to be alone (it was scary at the time). Mr. perfect on paper was just that, but fundamentally there were a lot of things in our conversation that I didn't see eye-to-eye with him on, but I ended up hiding the things I was passionate about that I thought he wouldn't agree with and struggling to find any minor similarity to play up. Needless to say he thought “faux me” was great and I was unhappily playing along thinking better to have someone than no one. About four or five dates later I very unceremoniously broke up with him (I use the term break up loosely), leaving him stunned and me feeling awful.

  3. AW says:

    My worst mistake on a first date was putting the guy on a pedestal without even knowing him – we knew OF each other, but had never spoken before. By treating him like God's gift from stage one, I unintentionally set the tone for the next seven months and blinded myself to his actual personality/behavior. (Why don't we listen to our friends??)

  4. Sharon says:

    My sister and I call this move the “Sullivan Pull-Back” because we both do it ALL the time! We are both able to convince ourselves at a moment's notice that THINGS ARE NOT RIGHT and we should back off immediately. And it's so true, but once you flip that mental switch your whole mindset changes and I find it impossible to get back to any previous feelings of happiness.

  5. Ella says:

    I made a huge mistake pretty consistently throughout college and my first couple years in DC. I'd go on dates with guys and find I wasn't really interested in them, but would be too passive and shy to actually say that. So it'd inevitably end up in me trying to avoid and put off future dates without having to say anything that might hurt their feelings. It was terrible, because instead of having a bad date and being done with it, I'd drag the process out for weeks or months and it always ended badly. It's only been in the last year that I've gotten assertive enough to just tell people when I'm not interested. It's still always a bit awkward, but it is so much easier for everyone involved.

  6. HB says:

    The worst mistake I ever made was while I was being walked home after a first date. We had just seen a great movie, had a great talk/walk to and from Georgetown and then he asked the fateful question “what do you want to do after you graduate?” (this was my senior year at GW) and I decided to give him my spiel about going into the Peace Corps and living in Africa for three years or more. As a 25-28 year old male the prospect of dating a 22 year old who was ready to move to another continent for the foreseeable future was clearly not appealing, he never called again.

  7. AD says:

    HB at least you told the truth! I'd call that a pretty good move on your part!

  8. CynthiaW says:

    Upon first moving to Texas, I made the mistake (after being asked about my religious preferences) of not stopping there, but mentioning that my sister had converted to being a XXX and that their beliefs were pretty whacky. Turns out the guy was raised in that religion and still believed everything – including the fact that the Earth was 10,000 years old and that dinosaurs were fictitious and the fossil record was a “trick of the devil.” (I was a geology major at the time.)

    After I picked my jaw up off the ground and tried desperately to find another topic of interest, conversation ground to a halt and we sat there awkwardly for another 30 minutes or so before I made some excuse about having to get up early the next day and ran.

    On the one hand, it kept me from wasting months with someone who I had a fundamental difference with; on the other hand, it was an extremely awkward situation – especially since I had burst out laughing at the line about the fossil record and then realized that he wasn't joking.

  9. Ms. C says:

    Interesting post, Belle. I think the most critical error I made on a first date (and I made it many, many times) was to announce “I’m never getting married and I’m never having kids.” During my twenties, I was very vocal about my desire to not get married and to not have children. In fact, I would go on first dates and say that I was “not at all interested in marriage,” didn’t see “how two people could stay together for their entire lives,” that I “didn’t have the maternal instinct,” and myriad other statements that I thought made me a progressive, modern, strong woman.

    It took me a long time to properly articulate my motivation behind this edict. Looking back, I know there was a part of me that did view the institution of marriage as incredibly flawed and one I was hesitant to embrace. However, that wasn’t really the point. I finally realized (at 28) that I felt so strongly about stating that I didn’t want those things so as to avoid having marriage and kids as my default. I felt (and feel) that too many women think, I “have” to get married…and end up settling for the wrong partner. Or, I “have” to have kids…and end up leaving before they leave (as Sheryl Sandburg puts it). So I took the opposite approach and set my default as never doing either.

    I don’t think setting your own default is problematic. However, the problem with entering a first date with this mind set – and, even worse, announcing it forcefully – is that you are preventing (even warning against) the other person from ever engaging in any sort of meaningful, long-term exchange. After you make that announcement, it doesn’t really matter how long you are with the other person, or how dizzyingly perfect it is at times, they never really feel stable.

  10. DGL says:


    I like reading your blog for gems like this. I stumbled upon your site several months ago while i was searching for men's fashion blogs in DC and i've come to enjoy these discussion posts as well as the ones where you share your thoughts on Hill life.

    Having said that, i enjoy reading a woman's perspective on worst mistakes made on first dates from what's been shared. I think it's so interesting that the majority of “mistakes” have been identified as things that were said or felt. In my experience, i think my mistakes have been things that i've done. (and i realize speaking is something you can “do,” but i mean physical actions)

    The beginning of my previous relationship was a bit rough. I knew the girl from college and had been communicating/flirting via text/online and talking on the phone for several weeks before we saw each other. It was long distance. When i saw her, i felt that we had said so much to each other, and expressed enough interest in one another that i could take the liberty to kiss her, which i did upon seeing her. She was a little taken aback and flustered after that, so much so that she didn't even do what she had wanted to: hold hands. (later on in during our relationship she told me this)

    The dating “scene” is one i've always tried to avoid, but being single now i certainly remember that as something to not do in the future. Unless i get a clear go-ahead, right? But recognizing what that looks like is a whole 'nother blog post.

  11. Loved this, Really well-written and insightful. Thank you.

    I think the biggest mistake I've made on a first date is that I wasn't honest about what it was. True, he kind of wimped out (“you promised you'd show me your favorite restaurant…how about Friday night?”) but I told everyone it wasn't a date, when they saw that it clearly was. As a result, I didn't take it seriously, felt uncomfortable, etc. By the time I was honest with myself about my feelings for him, he had given up. He was clearly at fault too but I wish I hadn't gone overboard with the low expectations and instead been honest about the signals that he was sending.

    However, it turned out for the best. He is happily dating my best friend, and I can't imagine myself with him. haha

  12. Jenny says:

    Biggest mistake I ever made was after the date. I told him I would love to see him again but then mentioned to a mutual friend that I wasn't really interested. She told him! He sent me an email that gently let me know he had “heard through the grapevine” how I felt, and it was fine. I was utterly ashamed. I was also 22. I try to be more upfront about my feelings now (and choose my confidants more wisely).

  13. Nicole says:

    I wasn't even aware of the biggest mistake I made during one of my first dates. It was a few months before I was graduating from law school and moving to DC. I apparently mentioned several times that I was leaving in three months!

    The great part is, he didn't care – he was planning on moving to DC too. We've been together for over two years! So my mistake worked out for the better.

  14. Laura S says:

    I must say that I've made some similar mistakes myself that have been mentioned in the previous comments. However, I have to tell you about the biggest mistake a guy ever made on a first date with me. During dinner, about 30 minutes into the date, he mentioned straight out that he was looking for a long term relationship and definitely wanted that to lead to marriage and kids with someone in the near future. Then for the rest of the date [approx another 2.5 hours], he kept mentioning how serious he was about wanting to have children, along with the fact that he wasn't sure he would be interested in even dating someone who didn't want kids, and that he even felt that adopting kids was not for him, as he felt a string urge/need to have biological children.

    This would have been just mildly to mediumly off-putting on its own, even though I give him credit for being up front about what he was looking for, EXCEPT, I was 26 and this was my very FIRST date after having a hysterectomy due to cancer, just several months previously. I had been very reluctant to start dating, as I was having a hard time coming to terms with both my cancer diagnosis and having surgery that made me infertile so young, but I had agreed to the date, as it was a setup by a friend who knew us both and of course thought we would be perfect for each other. So, needless to say, he had no idea about my recent medical issues and hearing all of this was very difficult for me and made me feel as if no guy would ever want to have a relationship with me, since I could not have kids.

    Unfortunately, rather than cut the date short right away, which I should have done then and definitely would do now, I politely continued the date till it ended, growing more and more uncomfortable, depressed and withdrawn. I actually burst into tears after I got home and did not feel emotionlly ready able to date again for almost a year. Even worse, he talked to my friend the next day and raved about how much he liked me and how he wanted to see me again. I think that even under normal circumstances I would have been reluctant to have a second date with him, as he seemed to have some serious issues about ensuring his genetic legacy, and now I can even talk about it and make it a funny story [in person].

  15. nadia says:

    I am so glad you wrote about this. I had a relationship for so long that every time I go on a date with someone I find myself comparing this person to everything my ex bf said or did. It's like my ex bf is the standard and I get lonely and sad after the date as well. Although it was my idea to end it bc of long distance, how do you move on to the next prospect?

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