Dating Experiences From 50 First Dates

Dating Stories

Thanks to Jenn Choi for asking my first question on Whale. Jenn asked about my funniest online dating story. Though I’ve been on 50 first dates or so, the number of dates that have a story worth telling are pretty small. Most of the dates have been pretty standard, although I’ve often wanted a date to throw up on me so I can have the killer dating story.

There was the time a date asked me if I was autistic. The worst part was that she was a special education teacher that worked daily with autistic high school students. In truth I wasn’t so offended and we’re still friends.

Once I went on a first date to an independent film festival that took place in people’s living rooms. The films were pretty funny. It was when I first started dating so I was somewhat awkward and for some reason didn’t my date to get a drink afterword. Because we were silently watching films the whole date we didn’t get to know one another and she had no reason to accept my second date invitation. Rookie mistake.

I’ve gone on a first date twice with the same person, though she didn’t remember our first date.

I’ve had my share of awkward dates where we sit on opposite sides of the table, sipping on our old fashioneds and staring awkwardly past one another.

Previously, I’ve written about a number of strange date cancellations I’ve received.

Perhaps the most interesting date experience I’ve had — and the one I discussed on Whale — is the time I went on a three-way date with a woman, let’s call her Bridget, and her boyfriend. This occurred because I had gotten myself somewhat involved with Bridget and she was in an open relationship. This was completely for the experience you must understand.

By this time Bridget and I had gone on probably three dates and she had sent me a questionnaire by email that required me to fill in my relationship and sexual history as well as my sexual preferences. However, before we became intimate she wanted me to meet her boyfriend. The three of us went to Thai food and then to bubble tea. Yes, it was awkward. Not the most awkward date I’ve been on though. We didn’t talk about the fact that I might one day soon become intimate with Bridget. I found it most awkward that they each paid for their own meal. Even with friends we often take turns paying I consider this ritual a display of friendship and intimacy. I can’t imagine splitting the bill with someone I’m dating.

Bridget and I dated for only another week or two and then, not wanting to actually be in an open relationship for the long run, I ended things and pursued another woman I had recently met. Like a handful of dates, Bridget and I are still friends.

Dating Tips

Here are a few tips and tricks I’ve learned from going on 50 first dates.

People Only Look as Good as Their Worst Photo
Maybe this is shallow, but people always ask. Perhaps this photo fact isn’t so surprising, people often put their best foot forward so almost by definition their photos are as good as they’re going to look. But listen we all look the way we look and shouldn’t be ashamed of it. And as we all know tastes in physical appearance vary widely. I think people should be confident enough in themselves to show what they really look like rather than trying to hide it. I’m 6’6″and in high school weighed a mere 150 pounds so you can imagine the teasing I was subjected to (even my basketball coach called me “sticks”). This self-consciousness has stuck with me a bit, but there I am in dating photos, chicken legs and all.

Occasionally someone comes out of left field and ends up looking much better than any of their photos. About 1 in 20 times someone will look so different from their photos that I wouldn’t know it was the same person.

Pay for the First Date (If You’re a Guy)
There is a common line of reasoning that says that whoever asked the other person out should pay for the date. Or that on a first date you should split the bill. It’s not 1950, but listen bro, just pay for the date. I’ve never not paid and I’ve never had a woman complain. I’ve had lots of female friends have guys not pay and they always complain.

I think most women appreciate this and chivalry isn’t dead. I keep this practice up until date three or four when eventually the woman begins insisting she will pay at which point I give in (after a while it become douchey to not let a woman pick up the check if she asks).

Create a Standard Date
If you’re going on a lot of first dates and are time constrained you really need to Mark-Zuckerberg-wearing-a-white-t-shirt-everyday your dates and just come up with something standard to do with everyone. Thoughtfulness is important, but on the first date you have no idea how you’ll get along so there is no sense in trying to come up with something creative. And trust me date planning can take a lot of you. Plus a large volume of creative first dates will leave you no first-time activities to share with your significant other once you do get serious.

I would also recommend making the date someone inexpensive as a matter of practicality. Going on 1-2 dates a week and spending $50+ each time can hit your wallet and feels even worse if the date is a dud.

Always do an activity if possible. Sitting across from one another eating dinner or finishing your drinks becomes very awkward if there is no chemistry and conversation subsides. An activity gets the blood flowing, loosens things up, and provides context for conversation. If you do get a drink try to sit at the bar side by side unless you are a skilled conversationalist. Make sure you are no positioned in front of a bar mirror. Even better, sit near a window where people watching can spark conversation and fill the silence.

I have two go-to dates. In the summer I buy my date froyo and we walk Greenlake in north Seattle. It’s beautiful and one of my favorite places to go anyway. In winter we play indoor bocce ball. I ask my date first of course and if they object I come up with an alternative.

These dates also offer an easy exit if things aren’t going well or the option for more fun if they are. Finishing a loop of Greenlake, for example, offers a natural break to part ways or a chance to walk across the street and grab food or coffee.

Second dates moving forward I try to do something fun and a little original.

Chemistry on an App Doesn’t Equal Chemistry in Real Life
It was somewhat surprising to me when I first discovered this, but it has held true. Often a date and I will banter back and forth over text, but when we meet in person the chemistry quickly fades. Other times the chemistry remains. Still other times answers over text are terse and I wonder if we should actually go through with the date, only to discover that in person we hit it off. Don’t rely too heavily on texting chemistry as measure of what the date will be like.

Links

1. On epistocracy

An interesting idea many will despise:

Epistocracy comes in many forms. An epistocracy might give everyone one vote, then grant extra votes to citizens who pass a test of basic political knowledge (such as the citizenship exam). Or it might grant the right to vote only to citizens who pass such a test.  Or it might instead hold an “enfranchisement lottery”: Immediately before an election, choose 10,000 citizens at random, and then those citizens, and only those, are permitted to vote, but only if they first complete a competence-building exercise.

Trump would have likely fared better under an epistocracy.

2. Apparently cows like to milk themselves

3. The Sinbad genie movie (very interesting)

4. Reddit has a meme economy

5. What’s the most mysterious photo ever taken?

6. Soviet era minced meat commercial is strange in many ways

Why time management is ruining our lives

That is the title of a profound article from The Guardian. There are many points of interest.

One of the sneakier pitfalls of an efficiency-based attitude to time is that we start to feel pressured to use our leisure time “productively”, too – an attitude which implies that enjoying leisure for its own sake, which you might have assumed was the whole point of leisure, is somehow not quite enough. And so we find ourselves, for example, travelling to unfamiliar places not for the sheer experience of travel, but in order to add to our mental storehouse of experiences, or to our Instagram feeds. We go walking or running to improve our health, not for the pleasure of movement; we approach the tasks of parenthood with a fixation on the successful future adults we hope to create.

The article concludes that productivity is just a way to avoid asking and answering hard questions about how you’re living and a way to artificially feel immortal in a existence that always ends in death. Do read the whole thing.

You can seek to impose order on your inbox all you like – but eventually you’ll need to confront the fact that the deluge of messages, and the urge you feel to get them all dealt with, aren’t really about technology. They’re manifestations of larger, more personal dilemmas. Which paths will you pursue, and which will you abandon? Which relationships will you prioritise, during your shockingly limited lifespan, and who will you resign yourself to disappointing? What matters?

Extreme Forward Thinking

Via The Seattle Times:

…an Amazon patent document published in April: flying warehouses held aloft by blimps.

It would float above a city at 45,000 feet of height, and hold not only thousands of items, but a fleet of drones.

Gravity would make the drones more energy efficient, as they wouldn’t have to power up until they’re close to the ground.

The drones could make their way back to the mothership in a shuttle, accompanied by packages and workers not afraid of heights. It could move to hover over other cities based on demand.

That futuristic vision is preceded by a discussion of Amazon’s Voltron-like drone patent.

Very Brief NBA Post

  • Russell Westbrook has the highest PER in the NBA, but the lowest True Shooting % of any player in the Top 30 (ranked by PER).
  • Eric Gordon has more 3’s (121) than Steph Curry (120). Through 32 games last year Curry had 140 3’s despite missing two more games. Curry is averaging under 40% from three-point range despite a career average of 44%.
  • Jeremy Lin has a higher PER than Klay Thompson, although in fairness Lin has been injured and played in only 1/3 the games. Still Lin is having his best season.

Do we think this NBA season is better than last? For some reason I find the major story lines this year less compelling than the 2016 season. Yes, I know Russell Westbrook is averaging a triple double and is well on track to finish out the season that way, but gimme Steph curry hitting 5 crazy threes a game. The Warriors narrative of a super team with Kevin Durant hasn’t turned out to be nearly as fascinating as last year’s team that set the NBA record for wins or even the Cleveland team vying for redemption.

Indian vs. Native American

I was surprised to find out the term Indian is not as offensive as I understood and in some cases is preferred over the term Native American. For example, see here, here, and here.

Unsurprisingly there are many different points of view.

From PBS:

A 1995 Census Bureau survey that asked indigenous Americans their preferences for names (the last such survey done by the bureau) found that 49 percent preferred the term Indian, 37 percent Native American, and 3.6 percent “some other name.” About 5 percent expressed no preference.

Moreover, a large number of Indians actually strongly object to the term Native American for political reasons. In his 1998 essay “I Am An American Indian, Not a Native American!”, Russell Means, a Lakota activist and a founder of the American Indian Movement (AIM), stated unequivocally, “I abhor the term ‘Native American.'” He continues…

I prefer the term American Indian because I know its origins. … As an added distinction the American Indian is the only ethnic group in the United States with the American before our ethnicity.

At an international conference of Indians from the Americas held in Geneva, Switzerland, at the United Nations in 1977 we unanimously decided we would go under the term American Indian. “We were enslaved as American Indians, we were colonized as American Indians, and we will gain our freedom as American Indians and then we can call ourselves anything we damn please.”

From Jessica Lee on Quora:

As with any cultural group, you will find that different people prefer different things. Personally, while I don’t feel that most people I have met use the term Native American maliciously, I do feel the term is… maybe minimizing is the right word? Hard to describe but what I mean is that there are hundreds of tribes and each is unique. The distinctive aspects and differences between the tribes are usually lost on the non native population. Anyone who knows me well knows I prefer the term Cherokee, I am a little less than half Cherokee on my fathers side. However, you just meeting me on the street, I wouldn’t expect you to know that, so Native American is fine, but try to learn a person tribe of possible. It’s usually the best option.

From Debora Spotted Eagle on Quora:

I prefer ‘First Nation’, ‘Native’, or ‘Indigenous’. I was born in the United States and an enrolled member of Canadian tribe, so to be called ‘Native American’ excludes the Canadian part of me (where both my parents were born). I don’t remember being referred to as ‘American Indian’ (if I were, it would be same as being called ‘Native American’).

I don’t mind ‘Indian’ although it’s the LEAST of my preference. I seems like a blah ‘name’ to me, like being called ‘Hey you female’ or ‘hey lady’, although both are true, they dont feel respectful or honoring, although I realize there might not be any disrespect from the one using it. I just prefer it LESS. Natives are honoring people’s in general.

A Stretch of Route 66 Will Play ‘America the Beautiful’ as You Drive to the Side

This is one of the weirdest, coolest, and most creative technological innovations I’ve seen recently.

As reported by Popular Mechanics:

Two years ago, the New Mexico Department of Transportation decided to spice up a particularly desolate stretch of Route 66 between Albuquerque and Tijeras by adding grooves in the road that will play music when you drive over them. If you drive the speed limit of 45 mph for the quarter-mile stretch, you can hear “America the Beautiful” play through the vibrations in your car’s wheels.

The grooves in the road work just like the rumble strips or “drunk bumps” that vibrate your car when you start to drift out of your lane. But these rumble strips are precisely positioned to create different pitches when you drive over them. The result? The notes to “America the Beautiful” rising from the bottom of your car.

Thoughts on New Whale Q&A App

Whale is a new app from Twitch (previously JustinTV) creator Justin Kan. The app attempts to connect tech influences with users that can ask direct questions. Influences then record videos that are up to one minute in length answering the question. Questions are locked and users must pay eight coins to unlock each questions. Influences charge a small fee to be asked and question askers get small monetary rewards when other viewers unlock the questions.

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I view Whale as mostly doing two things: (1) reducing search costs and (2) increasing access.

Reducing Search Costs

Many of the questions on Whale have already been answered in other forms. How many times have I heard Justin Kan recommend a trial period before startups hire key employees (especially potential co-founders)? (A lot). Likewise much of what Nir Eyal answers can be found on his blog.

However, even if a particular influencer has answered your question in a particular forum, finding that answer can be expensive. You may have to watch hours of interviews, read numerous articles, or begin following them on Snahpchat and try to reach out.

Whale reduces search costs since you can reach out directly to influencers and get an answer. The tradeoff for shorter search costs is higher monetary costs (you have to pay to ask questions).

Increasing Access

There are two aspects of increased access. The first is elevated status. Some users may view it as a measure of status to be able to have direct access to key influencers.

The other aspect of access is being able to ask a specific question to a particular influencer even if a similar question (but not the exact same question) has already been asked or if the same question has been answered by a similar influencer.

Implications

-The monetary cost of asking a question needs to be lower than the search cost of looking for a pre-existing answer.

-To truly act as a platform that reduces search costs discoverability needs to be improved. Qoura does a good job in this arena (when you type in your question a list of possible duplicate questions appears with good accuracy). This may include surfacing not only questions that have been asked, but the content of the answers.

-Whale should find ways to better let users find new influencers (if you liked a large portion of questions by Influencer X you may also like Influencer Y).

-Whale should find more ways to increase the status of question askers and improve interaction between influencers and question askers.

-Access is more valuable the more influencers that are on Whale.

-Access is more valuable if answers are longer.

-Answer quality needs to remain high. Some users are good at rifing and answering quite well off the cuff. Others go a minute and seem to say virtually nothing. Whale should go the AirBnB route and ensure the quality of answers early on remains high (and give instruction/tutoring/suggestions to ensure answer quality remains high).

I know from following the company closely that many of these improvements are in the work.

Things I worry About

-The platform becoming a forum for users to ask favors instead of questions (“Can you review our proposal?” or “Can you fund us?”) or ask aggressive questions (“Why did you donate X million dollars to racist/communist candidate Y”)  which will drive away influencers.

-Growth stalls which leads to quick abandonment.

-The mixed incentives between influencers weeding out duplicate questions and influencers answering duplicate questions to get paid leads to duplicate questions which reduces discoverability even given good search.

-Influencers getting asked so many questions they can’t answer all of them. This will either mean askers pay, but don’t get their question answered (reducing access) or the price of a question gets driven to, say $20-$50 a question, so that the average user is dissuaded from asking a question especially given the risk of low quality (the response could be a one-minute answer that isn’t helpful).

-Navigation/search/discoverability won’t improve (I view this as a really hard — probably impossible in many respects — problem that no one has really come close to solving).

-People in fact like longer form answers.

-People in fact like medium length, meandering conversations rather than specific short-form content.

-Asking influencers questions isn’t as interesting as we think or it is only interesting to a small group or it is only interesting for a short time before the fun wears off.

-Even given search costs there are so many existing resources online that Whale won’t catch on.

-Influencers are too busy to join Whale or sustain a high level of involvement (think about how many influencers started Snapchats and have since quit). This will lead to less influential, “regular people” most available to answer questions, but users will not be willing to pay this type of “influencer” to answer questions.

-Whale will fail to catch on for complex, not fully understood reasons.

-Whale will remain a niche for the tech community rather than expand to other types of content (which I actually view as fine).