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.

3 thoughts on “Online Dating Diaries”

  1. Interesting post! There’s still a lot of stigma surrounding online dating, but I’m glad to hear that you’re being open-minded and giving it a try. Moving to a new city can be tough, but it sounds like you have a clear idea of who you are and who you want to be with.

    All the best to your pursuit of love 🙂

    Liked by 1 person

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