Tag Archives: Technology

Online Dating Diaries

When I moved to New York City, I saw a subway ad joking about the difficulties of dating in New York. I laughed inwardly, secretly glad I’d dodged that bullet.

And then all of a sudden, I hadn’t. As many readers of this blog have likely deduced, I was in a relationship for a very long time and when it ended, I found myself lonely and single in a city not known for its warmth and friendliness.

Literally overnight, I became obsessed with rings. I caught myself looking at the left hand of every man or woman I saw, knowing full well that rings only tell a very small part of a very complex story. I remained acutely aware of the way I’d intended to switch the two rings I currently wear to add the new rings I assumed would be part of my move to New York. Suddenly, my naked left ring finger felt like a bright, flashing neon light of failure.

About five months later, I decided to start dating simply for the sake of having something to do.

I am pleased to report that it was thoroughly entertaining. While I’m in a perpetual state of peaceful sadness about everything leading me to singlehood in New York City, I’m not sorry I’ve had a chance to experience the storied world of dating here. I’ve found reasons to laugh and learned a bit about myself in the process, which is just about all I can ask for.

In that spirit, I present Online Dating Diaries, a chronicle of my dating adventures in a city quite unlike any other.

I. The Nice Guy

First, there was Navin.

Navin and I shared a Southeast Asia connection; I’d lived in Malaysia for a year and that’s where his parents were from. Navin grew up in the Bay Area but had been to Malaysia more than a few times and was also relatively new to New York. A Malaysian restaurant in the East Village seemed fitting for our first date. We had a lot to talk about and I genuinely enjoyed Navin’s company.


On my end, there were no romantic feelings. None at all. He walked me home one night and kissed me goodnight and I was confused because I didn’t know where that was coming from. We hadn’t even held hands! Doesn’t that come first?

After about six weeks of exploring various restaurants and bars and even the Natural History Museum with Navin, I asked my roommate for advice. “You don’t owe him anything,” she said. “You’re allowed to like spending time with him. You’re allowed to just be friends.”

Oh. Right.

Lesson learned: Some people make better friends than romantic partners.

II. The Sober Guy

Shortly after meeting Navin, Jared’s online profile caught my attention because of a well-placed pun; I couldn’t help but comment. After telling me via text message that he’s 10 years sober, Jared suggested meeting at this really cool East Village tea shop. I agreed. As I told my carpool, I just wanted to find out what he had to say!

People have historically opened up to me with minimal prompting on my part so it only took about 20 minutes to learn that Jared entered rehab after almost dying of a heroin overdose in high school, that he is currently active in AA and NA, and that his family’s support was the only reason he was alive and thriving. He’d recently sold his photography equipment business and was back at school studying philosophy and journalism.

He was interesting and I was curious but I know what stage of life I’m in . . . and it’s not compatible with a full-time undergraduate still living at home.

Lesson learned: Stories come with baggage. Choose your baggage wisely.

III. Edmund

Though I usually admire perseverance, there’s a line. Ed ran across that line at record-breaking Olympic pace.


Lesson learned: Some people just can’t take a hint.

IV. The Short Guy

I like people who are open-minded. When Saul mentioned that he had recently taken up meditation, I was interested. I remained interested when he mentioned ballroom dancing and we went for drinks.

My heart sank as I walked up to the person standing at the entrance to the bar. Saul was about two inches taller than me. And that’s when I was no longer interested.

Shallow? Yes. And I could have overlooked the height issue, but Saul is yet another person my age who lives at home. And I just can’t overlook that. (Shallow? Maybe.)

Lesson learned: I’m rather petite and therefore biologically programmed to being attracted to people who are tall. Genes talk. Loudly.

V. The Other Short Guy

The first short guy, Saul, was the first date on the second app that I downloaded. This short guy, Alex, was the second. “You have to learn to read their shoulders,” a girlfriend told me. “Pictures of them with other people contain essential pieces of information.”

Alex was a lot of fun because he has a Ph.D. in neuroscience, which of course meant we talked about The Big Bang Theory. As Alex explained to me, though, he did the Ph.D. because he didn’t know what else to do after undergrad and now he works for a luxury car company figuring out algorithms that will sell more cars.

Alex went on vacation for a couple weeks right after I met him and I completely forgot about him until he messaged to see if we could go out again.

I have always been very out of sight, out of mind.

Lesson learned: Shoulders. Look at shoulders.

VI. Three Men on a Train

New York City is not known for friendly people who say hello on the train, but I’ve been interrupted three (three!) times on the train because of men who have asked me what I’m reading. So maybe New York is really full of friendly train opportunities that we just keep missing because of a stereotyped view of uptight New Yorkers.

. . . . Nah.

As a rule, if I am reading on the train I want to keep reading and I don’t want to talk to you.

Furthermore, you just interrupted my reading, which means I don’t like you anyway.

The stories below are not online dating stories. These are stories of what happens when people stuck their noses into my books and struck up conversations with me on the train.

  1. A guy first asked what I was reading very early into my time in New York. I was still living on the Upper East Side and had been single for about a minute. I was a scarred, scared, sleepless wreck trying to acclimate in every way. I was also reading Spinoza’s Ethics. David commented on my choice for “a little light summer reading” and asked for my number before getting off the subway. He called later that night and we went out to a comedy club the next week. I wouldn’t let him kiss me goodnight and then lied to him about where I lived, forgetting that he’d probably notice when I went in the building next door. I’ve grown a bit more graceful but haven’t heard from him since.
  2. An older man struck up a conversation with me on Metro-North about the same book. Half an hour later, he concluded, “It’s nice to see young people reading about ideas.” Good sir, this young person was reading about ideas and then you interrupted her and she spent thirty reading minutes talking to you instead. Have a wonderful day while I get back to my book.
  3. I was reading Ethics in the Real World by Peter Singer when a man in his early 30s sat down next to me on Metro-North (maybe I should stop reading on Metro-North) and struck up a conversation. He told me a pretty interesting story about becoming a cop because he wanted to improve communities, and ended up telling me about his relatives who hid Jews in Romania during the Holocaust. He asked if I’d like to get a drink and discuss philosophy and there’s really only one answer to that. So I gave him my number and he said he’d definitely call. Thing is, he’s a cop. And he probably looked me up and found all sorts of information, including this blog. He never called and I’m not surprised. I’m probably too something. Too opinionated, too passionate, too determined. Damn right.

Lesson learned: Put in headphones while reading. Then they really know you don’t want to talk to them.

VII. The Teacher

Ben was the first person I went out with who I was actually attracted to. Immediately. He was the first person who left me disappointed when he didn’t kiss me goodnight or reply to my, “Thanks for a lovely evening” message. Ben’s a teacher at a middle school in Brooklyn and we met shortly after the whole Betsy DeVos debacle, so we had a lot to talk about.

And then Ben asked a question I really didn’t like and I knew that was the end of that: “How has your (insert name of dating app here) experience been?”

That’s the part where I explain that I’m pretty new to the dating scene and really not looking for anything in particular but open to whatever comes along. That’s when I sound wishy-washy, which I don’t like at all. But since I don’t want to lie, either, I just can’t win with that question.

Ben, as it turns out, was looking for a wife. He suggested we call it a night about two minutes later, telling me that it’s important to have some fun in the dating world and wishing me luck.

Thanks for the advice?

Lesson learned: I have a very deep soft spot for kindred spirits. (And according to Moral Tribes by Joshua Greene, another book I was once reading on the subway, I’m not alone.)

VIII. The Guy Who Needs a Teacher

This really happened.


I sent the screenshot above to five girlfriends aged 24-31. All five of them separately replied, “He doesn’t know what entails means.”


This is the guy who prompted me to borrow Modern Romance by Aziz Ansari from the library and then to write this post. I still get a kick out of it because this conversation absolutely should have gone the other way and he could have crossed that off his bucket list. Such a shame.

Lesson learned: Books > Boys

IX. The Stalker

So far, I’ve given you an account of six people who I enjoyed meeting and who gave me, at the very least, an entertaining story for this blog. I wish them all the best.

I did have two experiences, however, that frightened me a little bit.

While we were texting, Boris said he felt that talking on the phone was a better way of making a good first impression, so he asked if he could call me. I said I’d rather meet in person to form a first impression but gave him my number.

Wrong choice.

He told me he’d call later and I didn’t reply. After all, I’d already told him I preferred to meet in person (read: not talk on the phone). He messaged to ask if it was a good time to talk and I didn’t reply. He called and I didn’t pick up. Twice. Then he messaged to ask why I hadn’t picked up. Then he went back to the dating app to ask if I usually gave out my number and then ghosted. The next day he called again. And messaged. Again.

And then I blocked his number and deleted the connection on the app.

It’s one thing if you want to give me a call. It’s another if you ask if that’s okay and then when I say no, you ignore me and do what you wanted anyway and then harass me about why I didn’t like your idea. I am still not going to like your idea.

My mistake here was giving him my number. I was trying to gauge how much he respected my opinion and also give him an opportunity to make plans to meet in person. This was a test, Boris, and you failed.

Lesson learned: Some people are creepers. Stay far away.

X. The Guy with Two Faces

This is the guy I almost didn’t go out with because he was so nice to me when we were chatting leading up to our date. It made me uncomfortable.

“How can he say all these things?” I demanded of my therapist. “He doesn’t know me at all! He’s never even met me!”

“Maybe he’s a good judge of people,” my therapist suggested. “Maybe he can guess more about you than you’re giving him credit for.”

“Maybe, but that doesn’t mean he can call me all these sweet names. That’s just throwing around words if he’s never even met me. And then it won’t even mean anything if he has met me because he’s already used them.”

My therapist sighed. “Just go on the date and try to be a little open-minded. Just try.”

So I tried. Dani and I got along well and went out a couple times. I found myself thinking about him during the day, looking forward to seeing him, and feeling excited each time I turned on my phone to see a new message from him.

But he said and did a few things that concerned me. He put me in a few situations where I found myself looking for a way out. I found myself using words like “stop” and “no” and “it’s fine”. It wasn’t fine. So then, as an out, I made up a story what I was doing one evening; he made his disappointment very clear and I haven’t heard from him since.

Lesson learned: No means no. Period.

Lessons Learned

Someone once told me I’m a lot to handle. That’s probably true, I make no apologies for it. Going out and meeting people, however, reminded me that I’m perfectly capable of being friendly and open, carrying on a conversation, and making others feel at ease. It made me more willing to explore, try new things, and generally take risks. In short, a few months of dating have made me more confident and I’m glad.

Dating also forced me to confront the guilt I often feel when I don’t think I’m giving people what they want from me. There was one particular situation where everything went much more quickly than I’d wanted and I still emerged feeling badly for not doing enough and embarrassed at my inability to put a stop to everything taking place. Dissonance much? I told four girlfriends about what had happened and asked what to do in the future. All replied, “Well, I’m not really good at that but . . . ” and proceeded to give the advice I’d also doled out to many girlfriends: “If he gives you a hard time for any reason he’s not worth it,” they said. “But yeah, I never know what to do in those situations, either.”

That experience of guilt and embarrassment wasn’t entirely new but it prompted a flurry of questions that I’d always swept under the rug: What is it about a nice evening that makes me feel like I owe you something? What makes me feel that I need to fulfill whatever need you have before taking my own into account? And as a woman, how do I acknowledge having those feelings while also affirming for myself that I am well within my rights to stop when it’s time to stop, without having to provide or justify a reason?

Unpleasant experiences can sometimes be the most valuable and I’m lucky to be in a position where the benefits of asking the questions more than outweigh the costs of the negative experiences.

The Next Chapter

A few years ago I was modeling for a friend’s photography project and wrote the following caption on one of her photos:

Girl, 22, charming but with a little OCD, intelligent but unable to calculate percentages; loves laughing, historical fiction, acoustic music, learning, superhero movies, cuddling, being outside; honest to a fault, discusses politics on the fly, looking for someone to love.

I was single at the time, but got back together with my then boyfriend about a month later. What’s funny to me is that nothing has really changed. I read more nonfiction than fiction these days and spend more time writing than I used to, but everything else is accurate. I have two (currently inactive) dating app profiles that say the following:

Educator, traveler, reader, and blogger. I love learning, black coffee, and friendly people and I plan to change the world.

Canadian born, upstate New York raised, worked in Southeast Asia, now calling NYC home. Always looking for new places to explore.

I’m moving again soon (details to follow!) and will continue the dating adventure. This time, though, I will be looking for something. Or, more accurately, for someone. I might be coming late to the “find yourself” party, but better late than never having done it all.

The Perfect School Day

It’s probably clear from this blog by now that education is very (dare I say “increasingly”?) important to me. I’ve written a lot about education in general, and more specifically on the purpose of education. Much of what prompted those posts came from reflection and discussion with a friend when I was working in Singapore. 

Here are some of my past writings on education:

We’ve also literally written thousands of unpublished words on the topic, including over 10,000 words in an unfinished e-book that has been on the back burner for months, but spurred on most of my education-related thinking over the past year or so. I’ve rethought a lot of what I “knew” about school, teachers, and students and I’m excited about the possibility of true education reform.

So with all the abstract philosophical thought on the topic and much reviewing of the educational literature, here is a complete “perfect day” of secondary school as my friend and I envision it.

The Daily Schedule
9:00 AM – Start of school. This isn’t super important, other than it isn’t super early. Many high school students naturally sleep in a bit later due to staying up later and there really isn’t any reason to begin at 7:00 AM.

9:00-10:30 AM – Reading. Ideally this is aimed at current local, national, international, or global problems with current events from the news or other texts. The goal is simply to be aware at the beginning of each day of the suffering that is taking place all around us. This is not done to instill pessimism, but to inspire compassion – the desire to alleviate suffering in others. Literature that deals with human created suffering such as Frankenstein make for good selections during this time as well.

Conversation. This is a time to discuss what’s been read and share what interests and engages us. There can be a specific topic for this first hour, say sex trafficking of women around the world, or more open-ended reading of current affairs and sharing issues of personal interests. The aim is simply to engage in meaningful conversation about the state of the world with the purpose of refining ever more acutely what causes suffering and understanding the variety of contexts that contribute to it.

Investigation. This is a time to investigate what solutions have been generated for the causes of suffering we’ve been reading and discussing and to figure out what we can do as individuals, a group, and a community (both locally and societally) to alleviate it. This should spur lots of insight and opportunities for the social entrepreneurship block to come later in the day as possible gaps are identified in current attempts to deal with issues. Students might investigate political, economic, social, or technological solutions that have been attempted to deal with world problems.

10:30-11:00 AM – Break. This is a time to simply relax, have a snack if needed and transition to the next phase of the day.

11:00 AM-12:30 PM  – Physical education. This is a time for strength training, cardiovascular training, mobility training, and other athletics. This is also an opportunity to meet in small groups or one-on-one to discuss nutrition, mental health, and emotional health in order to increase and monitor overall well-being. The aim is pragmatic, how do we take care of ourselves as humans?

12:30-1:10 PM – Lunch.

1:10-2:40 PM – Social entrepreneurship. This is a time to work collaboratively on projects that aim to alleviate suffering and improve the world. Creativity, service, design, innovation, STEM, and business skills are intermingled in order to develop projects and programs that would have the greatest possible impact in any particular area. All members of the school community spend this time actively engaged in social entrepreneurship work, which could also include supporting one another’s enterprises, meeting with community partners and facilitators, and working off campus. This is also an opportunity to attend roundtable discussions to present work completed so far and elicit feedback from others, as well as figure out collaborative partnerships.

2:40-3:00 PM – Break.

3:00-4:30 PM – Personal growth and well-being. This is a time to end the day on a positive note, examining personal strengths, goals, and psychological states. This is also time to follow individual passions, such as reading literature, playing music, learning languages, creative writing, playing sports, making videos, blogging, or simply relaxing. The rejuvenation that comes from this part of the day will help the following day to commence with similar excitement. Engagement and flow should occur often and students can leave for the day feeling charged and full of zeal.

A Day in the Life of a Student
“Air pollution increases amidst warnings.”
“Migrants face deportation.”
“Refugees seek urgent medical care”

Maia stretches and looks up. It’s nearly 9:30, the end of the half-hour reading block that begins the day. Maia, her peers, and their teachers have been together as a team for the past year and a half. While they don’t always agree on how to most effectively tackle the suffering in the world, they care for each other and about those around them.

Soon, there’s enough movement to indicate that the readers are ready to talk. They readjust themselves around the room, remaining comfortable, but better able to see and hear each other.

“I’ve been reading a lot about climate change today.” The comment comes from a student perched on an ottoman next to a stack of books with titles like The Age of Sustainable Development.

“Did you see the New York Times article on the summit?” Maia asks, still sitting against the wall. “There’s a picture of the Doomsday Clock in my head.”

“I thought Canada put up a particularly strong stance, actually, and that might push other countries to follow through with caps on emissions.” A student new to the group states, sitting at a desk.

“That’s pretty broad, though,” says a student on the floor near Maia. “Yesterday, I read a lot of this book on the Copenhagen Consensus and there are real proposals that real people are working on, but it’s hard to tell whether emission caps are actually more effective than other suggestions, like bioengineering. On the one hand, it’s an easier sell. So maybe that’s better than nothing.”

The conversation continues for about thirty minutes and covers a range of topics from climate change to micronutrient deficiencies in small children. As always, the focus is on understanding why suffering occurs. Gradually, students return to their laptops and put in headphones, ready to move on from discussion.

Feeling agency to act is important. Maia and several classmates have lately been investigating vaccination efforts in Africa. They read Half the Sky together earlier in the year, which prompted questions about sex trafficking due to poverty, leading to a foray into tropical diseases. When they come across a new report on Ebola, one group member calls over a teacher to ask about virus mutations while others gather around a YouTube video explaining the science.

After about thirty minutes, it’s time to stop. Maia has learned to monitor her body for fatigue and tries to pause in her work before reaching a point of frustration. While some stay to continue working, Maia needs a half-hour of relaxation and maybe some frisbee. She takes an apple out of her bag and joins a loud group of friends on their way outside.

Frisbee leaves Maia feeling warmed up and ready to keep moving. She has a meeting with a nutrition counselor at 11, the beginning of the physical education block. After a long exploration of ethics and sentience, Maia has decided to become a vegetarian and wants guidance on her new diet. If she can’t take care of herself, she can’t make the world a better place. A guidance counselor taught her that last year after she experienced a series of anxiety attacks. After her meeting, Maia joins a group of classmates for a trail run in the woods on the edges of campus.

When they get back to the gym, Maia heads straight to her favorite coach. She wants to add mobility training to keep her hips mobile for the barbell squats she already does with the hope of squatting one and a half times her own body weight. She found a series of exercises online and asks for help with her form. The gym begins to clear out around 12:30 as students freshen up before lunch.

The afternoon campus is unrecognizable from the calm of the morning. Teachers, students, and community members are everywhere, all working on a myriad of social entrepreneurship projects. Maia’s group is putting together an education campaign about vaccination. They’ve partnered with another group focusing on fundraising efforts to implement the campaign. Each group takes a turn updating the other on what they’ve accomplished since their last check-in two weeks earlier. A teacher joins the groups to ask whether they’ve contacted any humanitarian aid agencies, which Maia’s group adds to their task list. Across the room, a few students and teachers are gathered around a whiteboard with a series of questions: “How do we create vaccines? What are they? Are there vaccines we don’t have, but would like to have? What’s been done to create them? Can we try making one?” Pointing this out to her group members, Maia joins in the discussion. This could be another good partnership.

It’s 2:45 by the time Maia’s group decides to stop for the day. They have a “next steps” action plan that should get them through the rest of the week. Other groups have already paused in their social entrepreneurship work and gone back outside to take a break.

Maia returns to her locker for her yoga mat and makes her way to an open studio space. After learning about yoga and meditation from a friend last year, Maia started an afternoon yoga class during the personal growth block. At the beginning of class, she invites each person to check in with themselves and set an intention for their practice. They’ll be in this space for an hour so she encourages them to focus on altruism, approaching each person with the goal of enhancing their overall well-being in every interaction.

After class, Maia steps over a robot whizzing down the hallway and follows the sounds of yelling and cheering to a room at the end of the hall. Someone mentioned a new virtual reality video game and maybe these are the people to ask about it.

At 4:30, Maia joins the waves of students leaving campus. She feels content, optimistic about the work she’s doing, and already looking forward to meeting with her project group again tomorrow. She makes a mental note to see what the team of teachers has been working on; she hasn’t really talked with them this week. Maia flips through her phone to a podcast recorded daily by a group of students.

“Good afternoon,” the host begins. “Thanks for joining us on What to Be. Today’s special guest is the executive chef at a local restaurant that provides job training and childcare for mothers.”

Maia smiles. That chef is a friend who graduated two years ago. Cool.

Final Thoughts
The actual blocked timing of much of this day ought to be more flexible than is written out here. It’s important that students learn how to manage their time and what is important. If they are fully wrapped up in a project they are working on involving social entrepreneurship, it is in no way urgent that they stop so they can move onto the final chunk of the day focused on personal growth and well-being; they are almost certainly already feeling a sense of personal growth and well-being if they are truly engaged in the project and feel a deep sense of meaning and purpose. Let them continue on.

The shape of this day is designed so that students can be exposed to problems early, work hard on thinking about and reflecting on them, take a break to physically recharge with exercise and food, move onto solving problems and creating value in the world for others, and then finish with some personal “me” time that explores what gives each of us pleasure and a sense of well-being. They will be prepared to act as responsible citizens who can think critically and participate in civic debates while also being ready for employment that is purposeful and creative. When not acting as citizens or employees they will understand how to relax and enjoy themselves in personal activities that contribute to a sense of rejuvenation and flow.

Learn, exercise, connect, create, be. Do our students really need to focus on anything else?

Reluctantly Dependent

I am not dependent on my iPhone. I am not I am not dependent on my iPhone. I am not dependent on my iPhone. I am not dependent on my iPhone.

I am not dependent on my iPhone . . .

. . . or so I thought.

I’ve had my iPhone 4S for about a year and a half and I love it. I don’t care that it’s a “cool” product (or, I think it is), I don’t care that it’s a status symbol (my model is so old that it’s really not anymore), I don’t care that it has the potential to run a million apps (I only have 14). The reason I love my iPhone is because my mum, dad, brother, sister, and closest friends from home have iPhones so we can still iMessage, even though we’re thousands of miles apart. I didn’t realize how important that was until moving overseas in August.

And then my iPhone started to unravel. It grew increasingly glitchy after I installed the iOS 8 update; with the more recent update to iOS 8, my phone became even more temperamental.  “I’m going to need a new phone,” I kept telling myself. I just didn’t expect that iMessage crashing would be the reason for the new phone.

A couple days ago I tried to send an iMessage and got an error message that iMessage was deactivated. When I tried to turn it back on, my phone beeped with an error – every 7 minutes. As I was trying to sleep at the time, I grew increasingly frustrated and, in fact, resentful. “Why are you doing this to me?” Silence. A factory reset and reinstalling the operating system did nothing to alleviate the problem. After a traumatic night when the phone wouldn’t even turn on and I had to download a widget onto my laptop to use as an alarm clock, I decided that enough was enough.

In moving overseas, I have learned that there are a few creature comforts and concessions to “the old life” on which I am not willing to compromise. For example, it is imperative that I buy fresh produce, no matter the cost. It is also essential that I can communicate with my family literally with the tap of a finger.  (Unfortunately, cost is a factor here.)

Long story short, I am dependent on my iPhone. I’ve come to terms with that over the last few days upon feeling my heart sink every time I think of a quick message to send and realize that I can’t. Looks like this weekend’s shopping will be more than just groceries!