luis is a co-founder and social software architect at he likes building small web toys a whole lot. More ...

Blog Index
The journal that this archive was targeting has been deleted. Please update your configuration.
« 10 Great Movie/TV Opening Titles | Main | 9 Things I've Learned from 90 Days with a DSLR »

25 First Dates

The following is a small collection of moments and impressions on various first encounters over the past 10 years. It isn't chronological, nor is it ordered by preference. It isn't a definitive list either; if I've gone out with you or someone close to you during the past decade and you can't find any mention of it here, please do not take offense. It doesn't mean I've forgotten, it's more likely that I was simply unable to encapsulate our date into a three-sentence abstract. It's not you, it's me, as the old nugget goes. Please also note that some details have been intentionally modified, to protect the identities of the individuals involved. Coz you know, I'm considerate like that.

1. We're in a jeepney and I can't remember where the restaurant is. We step off, and I realize that I've overshot by nearly 200 meters. The sun is baking and I'm too embarrassed to look at her as we walk briskly to the corner. She pulls out a folding umbrella and says, "Hey, it's ok." At the restaurant, I realize that I underestimated how much the food cost, and am doing nervous math in my head to make sure I brought enough cash. She says, "Would you like me to share the bill with you?"

2. I'm at a pub, staring at my ashtray. When my date arrives she taps the tabletop in front of me to get my attention. She doesn't smile as she sits down. We talk for hours but every subject turns into a debate. She has a contrary opinion about practically everything, including topics that in my mind don't need to be argued over, like Radiohead or the efficacy of keeping prophylactics in your wallet. Months later, I realize that this is actually a pretty annoying characteristic.

3. We're sitting outside on an Ortigas sidewalk. It's past midnight and the call center kids are milling around on their smoke break. She's not a smoker yet at this point, and she watches me drag on my cigarette while we talk about emo bands. She says, "Further Seems Forever." I say, "Mineral."

4. I'm at a Starbucks, facing the sunset. My date walks up to me and the first thing she asks is if I've eaten. As we have croissants together, she talks, and crumbs fly out of her mouth peppering the black metal table between us. I find myself fixated on these for the entire duration of our conversation. I never see her again.

5. I'm in my car, and my date waves from across the drive. She walks up, steps lightly inside and apologizes for being late. She's smiling brilliantly at me, and I find myself developing proverbial butterflies in my stomach for the first time in 5 years. A week later, she leaves forever.

6. She has a little girl's voice and smokes like a chimney, her eyes backlit with what seemed like eternal amusement. When the bill arrives, she wants to pay for it. I consider this briefly until I notice that it's over 5k. I promise her that she can get the next one.

7. She's taller than me, in heels. She knows this, and shows up in flats. We're the only people in the restaurant and when the waiter arrives with a wine menu I confess that I know next to nothing about any of this. I can't tell if she does, but she doesn't correct me as I muddle my way through ordering.

8. The crowded bar is lit with colorful spotlights, and she shows up in body glitter. She walks towards my couch like I'm the only guy in the whole joint, and I instantly love her for it.

9. We're sitting across from each other in a booth at a Shakey's. I have a book I want to show, and I stand up to sit beside her. As I do so, she shifts away imperceptibly so that there's exactly 6 inches of space between us when my butt hits the seat. We don't sleep together until the third date.

10. We're on our second bucket of beer and when she talks she leans forwards like she's about to fall over. Around us waiters are stacking chairs and turning off lights. She tries to negotiate with one of them to let us take away a third bucket.

11. She's in a small black dress and we're dining al fresco. Her skin is almost completely white, and under the dim garden lights the effect is not unlike noir. For the first time in my life, I'm able to raise my hand at a restaurant and have a waiter respond within 2 seconds; they keep hovering around our table.

12. I'm at a bookstore, watching her legs take her from one pile of sale items to the next. She frees a Sophie Kinsella book from the stack, noncommittally leafing through it like she's waiting for something. I peer at her from across the mountain of books. Finally I lean forward and ask her if it's any good, "coz you've been reading it for like 15 minutes." I berate myself inwardly for the terrible pickup line, and the conversation becomes clumsy. The universe decides to give me a hand, and it begins to pour outside - big palm-slaps of rain against concrete. I start to relax. "Hey, we're trapped!" I complain, and her laughter is like wind chimes. I leave the store with her number in my phone.

13. She orders a Black Russian for me; I'd never tried it before. As I sip it cautiously we stare out into the Fort's unfinished landscape and talk about her lesbian experimentation back in high school. She tells me about a gorgeous ex-girlfriend, and how she'd introduce me when circumstances allowed. I chug, and order another.

14. I'm working while at a Coffee Bean, and she comes up behind me, and hands me a postcard. She's walked off before I can turn around. On the back of it, she's written the lyrics of my favorite Wolf Parade song, and a caricature of me working while at a Coffee Bean. Years later I'll randomly spot her on Facebook, and notice that she looks like a prettier version of the lead singer of The Yeah Yeah Yeahs.

15. It's 3AM and she hands me a magic brownie. It's moist and it makes popping sounds as the seeds are ground under my teeth. We talk about the businesses we're currently attempting to bootstrap, our growth strategies, and the likelihood of skipping the angel stage and going straight to mezzanine. Then we get the munchies.

16. We're sitting opposite each other, with Thai food between us. I observe that she has a smile that could light up a room, and she gives me an idea for a new webtoy. I release it the following week, right around the time I ask her out again.

17. I'm explaining the difference between ales and lagers, and my hands are grasping furtively at nothing under the table. She won't let me smoke in front of her and it's making me jittery. We have next to nothing in common and I have to stretch considerably to keep the conversation going. She's smarter than I am, which I find mildly disconcerting. Three years from this night, she'll get married and I'll refuse to attend the ceremony.

18. It's a humid summer evening and we're outside sharing my last cigarette. Our glasses of Grey Goose are perspiring into wooden coasters. She's telling me about ex-boyfriends but I'm distracted by her cleavage. She asks me a yes or no question, and I say, "Cool. Cool."

19. There's a row of empty beer bottles in front of us, and we're both talking slower. We're sharing deeply personal stories about previous sexual encounters, and her hand finds its way on to my knee. I look at it and wonder why I hadn't thought to do that. Then I notice my hand is on the small of her back. It had been there for so long that my shoulder had stiffened from holding the position.

20. We're crossing the street together and she has a black bolero jacket on over a tiny white tank. It's warm out, and she shrugs it off. She arches her back and unfusses her hair majestically as we walk. A guy on a motorcycle almost smashes into a car as he rides past us.

21. I'm at a party, working on tomorrow's hangover. She arrives late, better dressed than everyone else there. I swipe a bottle of cheap wine when no one's looking and, sitting together on a glass platform, we polish it off in about half an hour. She pronounces my name wrong each time she says it. It takes me a year to realize that this is perhaps on purpose.

22. We're at a bookstore, after school. She's pointing out which romance novels she's read. She doesn't look at me as she talks, her eyes darting up and down the shelves instead. Everytime our hands graze each other, my palms go sweaty. I am familiar with many of these authors and have actually read some of these books, but all I can do is nod impotently.

23. We're at her apartment and she's handing me a bowl of chocolate ice cream. It has pineapples and cornflakes in it, and I am inexplicably delighted. It's raining outside. We pass the treasured bowl back and forth between us until it's empty, then we turn and stare at the television. I realize 11 months later how appropriate a metaphor this was for our relationship.

24. It's Valentine's Day, and I have flowers. We're in the middle of a crowd, getting jostled by teenagers clamoring for beer. I hand her the bouquet, and she takes it without emotion. I see her, later in the evening, tossing them unceremoniously into the back of her car. Six years pass before I gather the courage to give flowers to anyone on V-Day again.

25. It's the night after her birthday and I hand her a large stuffed kitty. She keeps it on her lap the entire evening and when I lean forwards to kiss her good night, the kitty gets mashed between us. Many years later I will mistakenly buy this same stuffed toy again, and give it to someone else. I will not realize this dating faux pas until I sit down one Saturday morning to write a blog entry about twenty-five memorable first dates.

Reader Comments (60)

We sit in the school grounds, each sharing one half of my headphones as we listen to my walkman. I pretend to be nonchalant as the raindrops seem to have frozen in mid-air while my heart sings of joy that is beyond words. A decade later, I'm still not over her.

I guess I'm pathetic/sappy like that. Thanks for the nice post - now my brain's shifted into nostalgia mode once again.

May 25, 2009 | Unregistered Commentertundra

I like nos. 5 and 17 the most! :)

May 25, 2009 | Unregistered Commenterheidelicious

Same with tundra, I am now feeling very nostalgic.

#5 - Why did she have to leave?

#24 - Wow. I know how this feels. I LOL'd when I read it, what a familiar feeling that is!

May 25, 2009 | Unregistered CommenterHil

what a nice topic.

my most memorable date was two years ago. i was waiting at CBTL ortigas for 45 minutes for my date to show up. we've been talking a lot online before that but it's the first time we've ever met---anyway, imagine how pissed i was! i was about to leave but he showed up the last minute.

to make the long story short, i didn't find him impressive. i don't remember what we talked about. i don't remember any other detail except for the fact that the tea i drank gave me mild digestive distress.

well, i'm still with him two years later.

May 25, 2009 | Unregistered Commenterliz

tundra: you should put together your own list, i'm actually thinking about the possibility of making a webtoy out of this.

Heide: thanks! #17 left a bad taste in my mouth, but #5 was exceptional.

Hil: About #5, it's a long story. Glad you could relate to #24, it's one of the reasons why I have a real aversion towards giving flowers to anyone but my mom :P

liz: that would be a great story if i didn't know who you were referring to lol :P

May 25, 2009 | Unregistered Commenterluis

#5 was made overdramatic, you melodramatic drama queen

#'s 1, 2 and 24 sound so high school. what was this, a decade ago? :p

and this probably has nothing (or everything, hmmm) to do with the entry, but i noticed that almost half of these are post-yourmostrecentrelationship. word.

lizz: you met him online? really?! wow that's amazing.

May 25, 2009 | Unregistered Commenterclaire

#20 and 11 must really be hot. I get what you feel about #5. She sounds like those perfect girls who could pass as your soulmate, but you'd never end up with, or you've had met at a most inconvenient time. Being in a relationship for 5 years, the only thing I can relate to here is #25 hehe. 25 dates seem like a lot!

May 25, 2009 | Unregistered CommenterRussell

8, 11, 18 and 20 sure sound like hotties. :D

I like your idea and I was kinda wondering if I can ask you if I could steal this but I dunno if I can fill 25 slots LOL

Also, 5 and 17 sound really, really painful.

May 25, 2009 | Unregistered CommenterLarry

Claire: Hello, Capt. Obvious!

Larry and Russell: Well, you know that I have to say they were all hotties, in their own way.

Larry: Well, 25 is the max I could come up with without writing about _really, really_ recent first dates, and I didn't want to start off a slot with "Yesterday, I was at ..."

If I needed to abbreviate this list, I'd probably go with ten, and pick out a mix of hot, weird and disappointing dates. But I wanted to put something together that was as _close_ to definitive as possible. Really depends on what you want your own version to sound like ;)

May 25, 2009 | Unregistered Commenterluis

#5: Arouch! I know how that feels.

Great list. I have a similar list, but in my head, and I'll never publish it.

May 25, 2009 | Unregistered CommenterLuna

claire: yes, we met online through mutual online and offline friends. :D he joined my favorite forum and he was a total asshole. our first real contact was when i told him (over the forum) that baguio was full of squatters. he got mad. lol.

luis: haha, i bet he'd get pissed if you showed him this. and then i'd hear no end of it later!

May 25, 2009 | Unregistered Commenterliz

oh gosh, also, sorry for the misunderstanding. -.-

May 25, 2009 | Unregistered Commenterliz

ok lol #5 seems to be the crowd favorite, but i suggest, if she made you feel that way, you should go after her!

May 26, 2009 | Unregistered Commenterjo

Хорошо что удалось отыскать такой замечательный блог, а то последнее время уже начал думать что инет это мусорка сплошная.

May 26, 2009 | Unregistered CommenterAvertedd

... in case anybody is confused, the" rel="nofollow">liz above is not my sister" rel="nofollow">lizz.

May 26, 2009 | Unregistered Commenterluis

Of course not. Because your sister Lizz knows who most of those people are. The benefit of being related to you, haha.

May 26, 2009 | Unregistered Commenterlizz

And also, #1 is a dead giveaway because when did you last go on a date without a car? Lol.

May 26, 2009 | Unregistered Commenterlizz

Даже и не придирешься!

May 28, 2009 | Unregistered CommenterYorikk

Dude I've been reading your blog for a long time. I didn't know you were Jon Osterman. :D

The way you remember all these details is amazing.

June 1, 2009 | Unregistered CommenterMix

Mix, thanks :P I experience past, present and future simultaneously, so it's easy.

June 2, 2009 | Unregistered Commenterluis

[...] by steffi in boys. No Comments In the spirit of Guttervomit’s 25 First Dates, here’s a few of mine in random order. All different people. Too bad I don’t have as [...]

Gee, I guess you don't get to meet too many *new* girls too often huh...

June 4, 2009 | Unregistered CommenterMarie

wtf™, dami naman niyan...hahaha. crap, i should have done that. nice read, man.

June 10, 2009 | Unregistered Commenterdamncoolasice

Great list. #15 - You wouldn't happen to be talking about listening to Massive Attack? If you are, that's a great way of writing it. Kudos.

July 2, 2009 | Unregistered CommenterJosh

I guess it's only fitting that I'm taking the 25th comments spot of your 25 first dates entry to complain about the fact I've never been on a date.

July 9, 2009 | Unregistered CommenterElizabeth

PostPost a New Comment

Enter your information below to add a new comment.

My response is on my own website »
Author Email (optional):
Author URL (optional):
Some HTML allowed: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <code> <em> <i> <strike> <strong>