The Dilemma of First Dates

MDJ Says: There are three things my Zee & I always talk about when on dates:

  1. Our hopes, passions, and dreams
  2. Things we’ll do when we’re married
  3. Snarky observations about other couples we see around us – especially when they’re on their first date

Couples on a first date are incredibly fun to watch. They’re eager, they’re hopeful, they’re fully locked into each other – but a lot of the time, they’re just so painfully wrong for each other.

Zee: He makes it sound like spying on first dates is a hobby. I think our fascination with couples on first dates stems from the fact that we never really had one of our own. We just kind of hung out with each other and ended up realising that “Hey, this is one person I can actually hang out with for the rest of my life!” Or something like that. I can say it was 90% laughter and 10% getting to know each other.

MDJ: You and I obviously do not agree with each other’s definition of a date. As far as I’m concerned, as long as one of you is kilig, then it constitutes a date.

Zee: The kilig has to be mutual! Or at least an expectation of a kilig moment.

MDJ: I’m an emotional guy! I’m always in a state of kilig!

Zee: We do wonder often how it would be or what we would talk about if we actually had an official first date. We’re not experts but we’ve both have had our share of first dates with quite a number of other people, and more often than not, they’ve been disastrous.

Bad First Date

MDJ: And so last weekend, we spotted a couple on their first date with each other. It was a car-crash to watch – painfully horrific, but absolutely spell-binding.

We spent the next hour or so on a Facebook live-blog we had going to chronicle their conversation.

First Date Chat

Zee: They were of course less than an arm’s length away, so here are the snippets we caught of their awkward conversation:


Zee's rendition of the couple on their first date, done on her awesome Galaxy Note 10.1.
Zee’s rendition of the couple on their first date, done on her Galaxy Note 10.1.

Girl: I love playing Final Fantasy! I just spend hours playing it.
Guy: Really? You’re a gamer? That’s cool. I once gave my ex-girlfriend three sets of Sim City.

Guy: What’s your favorite movie?
Girl: Well, I love…
Guy: Walk to Remember was such a touching movie, I cried especially hard in that scene where Mandy Moore was dying…
Guy: Have you seen “Inception“? I love movies that make me think. You know Chris Nolan? He makes me think.
Girl: …

*Awkward silence* Guy grabs his iPhone and scrolls furiously through the photo gallery for five minutes.

Guy: I’ll show you a picture of my sister. You know, we go out every Sunday. As a family.

Girl gets fidgety and plays with a candy wrapper for 15 minutes.

Girl: I go to Davao often so I’m not here most weekends. I love their food.
Guy: I love eating. I once cooked chicken for my ex-girlfriend, and she called me just to ask if it was really me who cooked it.
Girl: You’re making me hungry.
Guy: (Ignores her previous comment) You know, I’ve tried a lot of sports. But football really bores me. Boxing makes me sweat!

Girl: You know, I live really near here.
Guy: Cool. I chose the right place to meet up then. Welp, I need to head home early. Coding tomorrow, eh.

It was 7:30 p.m. and they headed home separately. There was no second date. We don’t know this for a fact, but would be willing to bet a jar of Speculoos Cookie Butter on it.


MDJ: We, of course, are incredibly fond of dishing out unsolicited information, so quite obviously, we’ve done a post-mortem of how this particular first date went, and figured out what exactly went right (not a lot), and what went wrong (DING DING DING DING!):



  1. Zee Says: Proper scheduling & venue. On a first date, and especially on a blind date, schedule it in the late afternoon over coffee. That way, you can easily skadoodle if it’s terrible (“Oh hey, I have a dinner to catch, I gotta jet!”) or extend till dinner and drinks if it goes well (“Say, why don’t we continue this over dinner? My treat.”).
  2. MDJ Says: Setting up an escape hatch for future use. Always make casual mention of a specific time-consuming hobby, or a relatively distant destination you frequent, so when asked out for a second date, you have a viable excuse to say no, i.e. “Oh, I’m sorry, I’ll be out of town all of next week!” or “Gee, I’d totally love to, but I have a 4am bike ride scheduled the next day!”

Aaaaand.. that’s it.



  1. Zee Says: Talking about the ex. That’s a major killer. If you’re friends with, or close to your ex, that’s fine, but you don’t have to bring it up all the time. Even if it’s to prove that you have cooking skills, and are thus excellent husband material.
  2. MDJ Says: Turning the whole conversation into “getting to know me” instead of “getting to know each other.” It’s perfectly fine to have a script in your head to get the conversation flowing – I used to literally have a sheet of yellow pad in front of me containing at least 10 interesting topics to discuss, back when I’d call girls via landline in high school! – but if you intend on asking questions, you’d better be prepared to listen and respond to the answers, instead of cutting off answers and re-directing the conversation back to yourself.
  3. Zee Says: Faking jock credibility. If you say that a sport bores you, you better have the body to back it up. If you don’t, best to say the sport got bored with you.
  4. MDJ Says: Ignoring opportunities to escalate the proceedings. Let’s face it – first dates are a game of call-and-response. If you’re interested in extending a coffee date into dinner, or dinner into drinks, or drinks into something else, you drop discreet clues for the other party to pick up, and articulate for you, so you don’t come off as too assuming or presumptive. Ignore these clues at your peril – you either come across as bluntly uninterested (not good), or slightly dim (even worse). I was aghast at how the girl left the dude a huge opening to extend coffee into dinner by stating how hungry she was getting – a simple “Well then, let’s go grab a bite!” in response would have been nice! – and the guy completely seemed to miss the bait. I suppose he may not have been interested, but I think it’s more realistic to assume he just missed the cue. And for this, I am utterly disappointed.
  5. Zee Says: Not offering at least to bring the girl home. Even if she seems like she would rather walk home than hear another word about you, it’s just right and proper.

Zee: First dates are always nerve-wracking, and always hit-or-miss. There is no cause for you to call a therapist if it doesn’t go right, because dates are meant to be fun and a great way to meet new friends. A first date usually lasts 2-4 hours and most of the time, we try to put our best foot forward and rush into letting the other party know who you are by recounting your life history or act like like a representative of the NSO doing a survey. We try to impress and create an impression as fast as we can, when we should really be listening and appreciating the person you’re with. After all, when you do get to have second date, you do need to have something to talk about too, right? The worst thing that could happen would be losing “The One ” because of the “Only One Date.”

Got any terrible first date experiences or advice to share? Leave a comment, or drop us a line via Twitter or Facebook!

One thought on “The Dilemma of First Dates

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s