Serial dating: an epidemiological analysis

About a month ago, I went on a date with a guy who was smart, interesting, ambitious, health-conscious, athletic, curious, passionate about environmental issues, and pretty damn good-looking.  The Venn diagram of our interests and passions would have had a decent chunk of overlap.

After one and a half hours of drinking in a bar, we walked out and proceeded never to contact each other again.

What are we looking for?

This has happened multiple times now. You meet for a coffee, have a great conversation about artificial intelligence, politics, homelessness in San Francisco. And you never see each other again. Occasionally, the romance lasts for a couple of weeks or a month. But ultimately it fizzles out like potassium being dropped in water.

In this blog-post, I explore 4 categories of reasons that I believe drive our serial dating behavior.

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I. There is a diminished need or want for sole companionship

In the day and age of TaskRabbit, Uber, food delivery services and online everything, the need for another human being to share the workload of living with has come down significantly. I don’t practically feel the need most days to have anyone to split errands with (though except for maybe doing taxes, because I haven’t cracked that one myself yet…).

In more primitive times and societies, marriage is partly a mechanism for living, which had a high task burden. Today, the task burden is significantly alleviated by all the apps and devices we have. In more traditional societies, the need for marriage also came from a strict division of labor and skills, which meant women needed men for certain tasks and men needed women for certain tasks. Today, no man needs a wife to cook for him. No woman needs a man to drive her anywhere.

Having eliminated this need, we venture into the wants category to see what desires may remain that could be fulfilled by a partner. The truth is even wants have been significantly diminished.

“Do you ever feel lonely?” I asked one of my dates.

“Not really” he replied “I have a roommate and tons of friends to go hiking and skiing with on weekends, and a busy job through the week”.

It sounded familiar, because it was my lifestyle too (minus skiing, I don’t ski…yet).

The San Francisco (and other big city) lifestyle is one of extended teenage-hood. You live with roommates well into your 30s. Here’s the catch for those of you wanting me to reflect on how sad it is:  it isn’t sad at all – it’s actually fun. It’s fun to alternate who you hang out with every weekend, to have stimulating conversations with tons of different people, exposure to tons of different activities, and all this with zero commitment to doing anything for anyone that may benefit them at your inconvenience.

But here’s the catch…living without love nearby is like living without insurance, it’s great until something bad happens. And with enough health and luck, something bad may never happen in our 20s or 30s or 40s, and there really may be no need for someone beyond your parents, siblings and select friends. Your risk aversion drives how much you search for a partner. In my experience, the boldest/most optimistic among us don’t crave partnership as much.

 II. We like being alone and the freedom it brings

“I like spending the day by myself” – anon girl-friend

For many of us, the truth is having the freedom to shape your non-work days the way you want has become a norm. Especially since during the week most of us are corporate slaves, the weekend is when we get to exercise our freedom. Deviations from this freedom norm are painful. And any kind of relationship will tend to involve some compromise on your freedom.

You also might be the type of person who is happy watching a movie by yourself; reading a book by yourself; going to a museum by yourself with the freedom to linger over any exhibit for as long as you like. I’ve typically been the type of person who constantly needs to be with someone, but a month or so ago I went to watch Jumanji on a Saturday night by myself, and had a great time. Who knew?

III. We know what we want, we won’t budge on it, and we can’t find it 

I think this is the most pertinent reason for most of us being serial daters.

“I know exactly what I want and you’re not it” said one of my dates to me once. (Gotta admire his honesty at least!)

After a certain age and certain number of dates and partners, many of us know what we want in vague terms, if not exactly. Though, I also believe many of us will discover that what we thought was critical wasn’t so important because we’ll be charmed/trapped (half glass full/half glass empty, take your pick of words) by some other variable.

It’s good to know what you want, but it’s probably a barrier to your love life to want too much, and want more than you can give yourself.

What are you expecting from your future partner? And is it really fair given what you will bring to the table yourself?

Perhaps we’ve taken optimization too far in our love lives. Perhaps we need to follow the wise words of Baloo the bear from The Jungle Book…

“And don’t spend your time lookin’ around
For something you want that can’t be found
When you find out you can live without it
And go along not thinkin’ about it
I’ll tell you something true

The bare necessities of life will come to you”

— Baloo

IV. We are waiting for fireworks: about these ‘sparks’ you speak of

I recently asked one of my dates (the first guy in this post actually!) for feedback. Interestingly, feedback in the dating field is extremely taboo. So let me dwell on that point a bit.

Pros of getting feedback:

• You might learn something useful that is either fixable (e.g. “talked too much”, “dressed too casual”) or just an insight on how you are perceived. We all have blind spots.
• They might say really nice things about you and then you get to feel a warm glow (he did!)
• You are probably never going to see that person again so the downside is small

Cons of getting feedback:

• You might hear something that could lower your self-esteem, and it could be unfixable e.g. “You’re too short” (probably common feedback for me, if anyone was ever honest!)
• They might not be honest/might be too vague
• Their feedback might be their unique perspective/preference and not widely applicable
• They might think you have low self-esteem/ liked them too much – and everyone who is dating knows, there’s no worse humiliation than someone knowing that you like them when they don’t like you 

Ok, detour on feedback over. I took the risk. The guy said “blah blah blah blah <nice things> blah blah blah…..Unfortunately I just didn’t feel a strong connection and never pursued further”

It made me think: a lot of us are walking into dates expecting some kind of supernatural connection or force between us, and won’t text back without it. I’ve done it too: not pursued people because of a lack of ‘Je ne sais quoi’.

When you look at relationships and how they started, I have heard a few stories of sparks happening (usually of ‘friends of friends’). I’ve also heard tons of stories where there was no connection or spark, but an affection between two people grew over time. Have I had a spark with anyone I met straightaway? Being candid, no. I did used to find guys instantly attractive and sometimes I still do, but it’s always the guys who every girl finds attractive because they’re visually attractive men  – so it’s not a spark exclusive to me or us.

I’m left questioning: Are we right to want a ‘spark’? What exactly is this elusive ‘spark’ of which people speak?

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Concluding thoughts

So where are we left with all forces seemingly pulling us away from the currents of love that also run deep in our psyche? For once, my friends, I have to say, I don’t have the answer. I just don’t know. But I hypothesize: May be serial dating isn’t all that bad as long as you know when to compromise. May be there is someone out there who is worth the glorious sacrifice of not going on a Saturday hike with friends. May be there is someone out there who won’t satisfy all your criteria, but you will accept them because you will never satisfy anyone’s criteria fully either, and someone will accept you.

And ultimately, like anything in life, Love is a gamble too. So for now, Happy Serial dating, keep at those frogs!

 

 

 

 

 

 

 

 

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The San Francisco Dating Menu

A couple of nights ago, I was talking to a friend who commented that he missed the Stiletto muse. I’ve had little time to write for my blog the past few months, but I do write in my journal most days (naturally it is mostly unstructured and highly personal) . However, I decided to share this one little snippet from my personal journal today. If the San Francisco dating scene was a cocktail bar, here’s my take on the core of what would be on offer…

Women, feelings, and recipes for drama

“Through all the drama – whether damned or not –

Love gilds the scene, and women guide the plot”

– Richard Brinsley Sheridan (Irish satirist, playwright, poet)

Prelude

Since moving to the US, some of my girl-friends and I were on a frenzied search for ‘one of the ones’. There are guys who have been searching too. But recently a male friend pointed out to me that the genders liked to conduct the search in rather different fashions…

What do women want but drama

It was a weekday night and I was plotting my Coffee meets Bagel strategy to conquer some guy with a promising profile. ‘This time I don’t want you to go crazy and pretend that you are in love with him’ advised my wise male friend. If you’ve read my previous blog-post (Theory X and Y) you will recall I wrote about a guy as ‘Prince Charming’. At the time, I had texted him for a week, and never met him in person. When the spell wore off, I realized I had been drawn to an image of him which I’d built up in my mind. I barely knew the guy behind that image, nor would I have been particularly willing to learn, because when the image is so strong and attractive, who wants to peel back the layer and check what’s actually there. (Furthermore, if Prince Charming is honest and makes clear to you he doesn’t like you in that way, you should back down, which I should have done earlier).

But anyways, this time I was meant to show some maturity and level-headed-ness characteristic of a woman of my age. It was all going well. I was rational. I was calm…Then in the dark of the night, I started day-dreaming about the CMB guy, imagining what our children would look like. We both have round faces so our kids would be so cute, thought I. And then imagining our MBA degrees hung up on the wall next to each other. And then the shame set in in dark waves. I had NEVER even said hello to this guy in person. I had NEVER heard his voice, and I had exchanged but a few messages on CMB.  And I felt so excited about him, I should have been checked into an insane asylum. “Failure is the mother of all success” says Pitbull. Sometimes, all it takes is another rejection to set you straight…

…Fast forward a week, the excitement was gone, as were all the dating apps from my phone. I stood in the hotel pool with my friend, looking at her beautiful skin and silky hair, and savoring her deep insights. We had been through a lot together. Synchronized stories of high highs and low lows, and then the calming realization that large parts of this drama was self-created and self-imposed, and created and imposed on women by other women.

In the Jacuzzi, that incubator of great philosophical ideas, one question came floating to the top of my mind: “Why do we women keep being so pathetic and desperate?”

Why? Why was the over-priced Harvard Alumni Cheese & Wine Singles mixer for 33-55 year olds full of women, with very few men? (I heard. I wasn’t there to be clear. Like really, I wasn’t).  “No guy would pay $150 to meet women” observed my friend. And yet women do,  in the hopeless hope that they will meet the man of their dreams at some canapéd event.

Why are we the ones who want to be friends after a fling when the guy can just walk away? Why do we want to know if his Launch Day was a success? Or how his trip abroad was? Why do we care so much?

Sure, some of us are unattractive (it’s just the truth), but there are other girls who are beautiful, intelligent, strong, healthy, funny, charming, all the good qualities…and yet searching for a relationship and obsessing over strangers as if their life depends on it. They are reading books on how to improve themselves when they could be writing these books themselves. They are going for expensive facials when their skin has a natural glow that anyone with eyes would appreciate. When nothing is wrong with them, and everything is wrong with the endless pool of sub-par men out there, women are still the ones hell-bent on ‘fixing’ themselves. Another guy-friend very accurately observed on his gender: ‘We think we’re The Shit, when really we’re just shit’.

Some of these women are searching so hard, that they don’t even see the mediocre guy in front of them and fall in love with some image of him. Eventually the rose tint fades off your glasses and you realize you are sleeping next to someone who is not particularly intelligent, has barely inspired you to do anything great besides watching some new YouTube video, who complains about doing a meager amount of work around the house, and who is always putting his needs first whilst eating up your time and mental energy. And sometimes you put up with it for months at a time because you so desperately want a relationship.

One of my favorite quotes, as I justified all the time I wasted on dating these past few months, used to be: ‘Something is better than nothing’. I’d say this to my friends, to my sister, to anyone who dared question why I was begrudgingly going for drinks with someone who I didn’t really like (“I want to give him a chance”), or why I was still texting someone who texted me in two-day intervals when he had nothing better to do. Now I confess: Nothing is sometimes better than something.

Women have the most to lose from a relationship or even interactions with someone who is not right for them, yet we are the ones chasing it, and guys are the ones being like ‘Omg I value my freedom. I can’t be tied down’.

Why do we do it to ourselves? I believe there are 3 main reasons and then 1 little one (I’m a consultant, there has to be 3):

1. We have a biological clock — Thank you Nature for this (sarcasm). But here I would like to invite some debate: perhaps the biological clock difference is not actually as great as perceived to be? Whilst post-35 is medically considered a ‘geriatric pregnancy’, you and I can both think of many women who have had healthy children post-35. In fact, my grandmother had her only child – my father – at 36. With the newest technology, and the option of adoption, we shouldn’t be as spooked as we are. But geez, women and men love to scare the hell out of women with this ‘tick tock tick tock’ talk which starts when you’re 26. Seriously.
2. We are creatures of deep feeling and want to love. When I was 15, I scandalously read ‘Shanghai Baby’ (It’s not that good. Mostly indecent. It is banned in China for being pretty sexual). I don’t remember most of it, but one quote that I remember even today: “The men were like envelopes for my love.” It’s true. The women I hang out with are women of feeling and thought. And that energy has to go somewhere. With our busy lives, we can’t give it to the causes that truly deserve it: animal rights, environmentalism, championing minorities, healing the sick. Our activism is mostly limited to sharing links on Facebook with some angry comment. And then you’re left with this beating heart that still needs to love and it wants to attach to something, anything. I understand these women, because I’m a feeler myself. When I told a few guys how I felt or how my female friends felt, they came back with reactions like ‘Why are you overthinking it?’, ‘Just don’t think so much’. Classic.
3. There are real societal penalties for ageing — ‘It’s all in your head’ is also not fair to say about most women’s issues. There is increasingly greater evidence to back up what we all intuitively knew. For example, women don’t negotiate in the work-place not because they don’t want to, but because they actually get punished for it. Similarly, women get punished for ageing way harsher than men. And so in our heads, it’s not just tick-tock-baby-clock but tick-tock-wrinkle-clock.  What can I say? As a society, we need to progress to caring less about women’s looks. I do my part for this cause by always looking shitty 🙂

And lastly, there may be a little, just a little, element of women loving drama and poetry — so even when there is no basis for it, we have to create it. This reason I find somewhat permissible. I’m Punjabi. I’m a woman. And that combination means I love drama more than anyone. But every now and again, I realize I have to take a step back and realize I can’t get caught up in the drama that I created, and actually start living in the air-castles I built up.

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In my next blog-post, I look at the air-castles that society and Disney built up for us right from the start…your jaded Stiletto muse is baaccckkkk and it’s time to get real again!

 

 

Theories of Love and Dating: Theory X and Theory Y

In the week of Valentine’s I got thinking about theories of love and dating. This blog-post is based on the dating experiences of myself and my friends – and I thank them for their generous contributions. 

Background

In management and human motivation, there is theory X and theory Y. Wikipedia explains it in better words than I can:

Theory X believes “that the average employee has little to no ambition, shies away from work or responsibilities, and is individual-goal oriented. Theory X style managers believe their employees are less intelligent and lazier than the managers or work solely for a sustainable income… Theory X concludes the average workforce is more efficient under a”hands-on” approach to management’

Theory Y is more optimistic.  Theory Y believes that “people in the work force are internally motivated, enjoy their labor, and work to better themselves without a direct “reward” in return. Theory Y states that employees thrive on challenges, and relish on bettering their personal performance. …”Theory Y” managers gravitate towards relating to the worker on a more personal level.” It is what I believe the more evolved companies of Silicon Valley imbue.

I’m firmly in the Theory Y camp. And reflecting on this got me thinking about the two theories of dating I want to characterize…

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Theory X of dating

Theory X is the prevalent philosophy of dating in many urban centers today. It probably started in New York, and is now gripping San Francisco and even pure Seattle! Theory X is about playing the game. The principles of this theory are:

1. People choose partners predominantly based on extrinsic characteristics such as looks and prestige
2. If there is no palpable chemistry on the first date, you rule the person out forever
3. Making yourself scarce is the best way to be desirable
4. A number of cleverly deployed tactics can lead you to ‘scoring’ (read: kiss, sleep, whatever your goal is) with the other side

So how do you know if your dating partner is playing theory X on you?

The signs of 1. are everywhere, and I have succumbed to them too.  In ‘How to get the Guy’, Matthew Hussey coaches women to increase the volume of men they encounter on a daily basis. One way to do this is to organize ‘mini-dates’ such as coffees on weekday evenings or even between work commitments. The idea is you don’t need to make a grand evening out of it, as time for grand evenings is a scarce commodity for today’s busy working woman. I liked Matt’s idea in theory. But the reality is I am absolutely terrified of coming across any guy I like without having prepared (manicure, dress, heels, make-up etc.). So this means ‘mini-dates’ and the spontaneity of romance were taken out of my life. Any date worth its salt was at least a 1 hour commitment before the date in which I attempt to make myself look as least like my natural state as possible.

The signs of 2 are the prevalence of ‘first dates’. Recently, I was talking to a friend who has lived in India, Europe and the Middle-east, and she was telling me about a mean guy who had been showing off to her about his dating life.

‘When he says he dates a lot, he means American dating’ she said.

‘You mean he’s just going on tons of dead-end first dates’ I asked. She nodded.

People talk about the number of dates needed to get a partner and the numbers I’ve heard range up to 100!

How can it be that we are all SO unique that we are swiping profiles of people who live in the same city, who have common friends with us, are filtered to our preferences, and yet we have to meet 100 people to find one who lasts for more than a month?!

May be it’s time to challenge Theory X’s assumption. I have been doing so recently by setting an ‘at least 2 dates’ rule on anyone who is not a complete ‘no’ on date 1, and I must say you will be pleasantly surprised that people can be far more charming and giving and vulnerable when they are more relaxed because they aren’t under the pressure of impressing a total stranger on date 1!

3- Make yourself scarce

Every now and again I reach out to friends for advice on what to write back or how to approach a guy. Much of the advice falls into the category I would call ‘make yourself scarce’. How often have you had the experience where you text someone asking a fairly simple question on Monday such as ‘How was your weekend?’ and they reply on Wednesday. And then you have to wait until Friday to reply about yours.

Another outcome of this theory is the short text. Here’s an example:

Girl: “Yes! I had a great weekend – I went rock-climbing. Ugh so many callouses! Then went to the library. And I’ve been reading the four-hour work-week and it’s awesome! Have you read it? How was your weekend?”

Guy: “Oh cool. Good”

Wah wah. I’ve looked at many girls phones and our observation is that they’re always texting a lot more than the guys. So it’s refreshing when a guy can actually put together a few words and ask you out with better than ‘Wanna grab food?” (an actual text I got once asking me out after a string of ‘oh cool’s and my favorite minimalist text: ‘k’).

4- The classic pick-up tricks part of playing ‘The Game’

Personally, I think people who like playing games should join a games club and put that energy to good use in Settlers of Catan or Pandemic or PowerGrid or whatever.

On a happy drinking day in Napa, a friend outlined a brilliant strategy for purely the joy of messing with someone:

“You should text him at 2 am asking ‘What are you doing?” and then 5 mins later “Where are you?” and then not reply until a week later”.

I was entertained by the arbitrariness of this idea, amused by the concept of making communication parallel a random number generator.

The sad fact is I have had communication patterns with people (and ok, I’ve been guilt of it myself) where it has been like a random communication generator. And it happens between friends too. To some extent, I’m like ok, we’re all busy, I get it that it shows as ‘read’ but you don’t reply until a month later when you all of a sudden send me 7 messages. But then if you are actually interested in someone as a potential, don’t go treating them like your ages-old friends!

The cruelest of these games that I and several friends have been part of is the one where someone acts like they’re really into you, you seem to have great chemistry, and then they just ghost you without explanation. This happened to a friend who went on FOUR dates with a guy who said he was looking for a serious relationship. He had put in a lot of effort on the dates, picking venues that related to their conversation. For example, she had said she wanted a quiet place, and he picked ‘Mozzeria’ – a restaurant that is owned and run by deaf people, where you have to use sign language to order food ). And then, all of a sudden, out of the blue, he just ignored her without explanation.

Part of me thinks this is more serious than just bad dating etiquette, it’s a moral issue. My definition of morality is related to pain inflicted on others. And confusion and rejection are a heady painful mix to impose on someone knowingly. So if you don’t like someone, a) grow some balls and tell them that b) don’t ‘practise’ your flirting skills on the date with them by acting like you’re so into them.

Head to Hollywood if you like acting

Theory Y of dating

Theory Y is a dating theory I recently discovered is still in existence!

Lessons in Theory Y from Date 1: There are second chances

I went on a date with a handsome guy to De Young museum. Firstly, he demonstrated the art of compromise off the bat. He asked me what I’m into. I told him I liked art, and he picked De Young museum for our first date. He wasn’t into art at all. But the fact that he’d gone for me warmed my heart a little.

The conversation chemistry wasn’t great if I’m honest. He was a man of few words, a handsome mystery.  In one hallway of beautiful paintings, I asked him ‘Which is your favorite?’ hoping to elicit a glimpse into his mind and personality. He walked around for 10 mins stopping by each piece, and then as I looked at his face expectantly he said: ‘None of them really appeal to me’. Wah wah. When we left De Young without even a hug, I was sure I would never see him again. Even dates that had gone ‘well’ had ended without a follow-up date, so there was no reason to expect this lukewarm one to go anywhere.

But he texted the next day…and fast forward 1 week, I said ‘yes’ to our second date playing pool. Now he was the connoisseur, I was the novice (yes, I’d never played pool before!). And it made me think, there’s something about demonstrating the principles you would hold in a relationship right up front: principles of compromise, of trying something new that may not interest you, of being forgiving, of giving someone a second chance.

Lessons in Theory Y from date 2: Prince Charming

Once upon a time, a dating cynic (me by this point, jaded by bad experiences) sent a very good-looking guy a message on Coffee meets Bagel. Note, this was in contrast to the Theory X advice I got from my male friend: ‘No, let him send you the message first. Wait a few days’.

This guy seemed simply too good to miss a chance on because of outdated gender norms. I messaged him, but didn’t expect he would reply. But he did, and he replied a long warm message. I sent him a long message back. And then magic – he replied straightaway. He was online! He didn’t apply theory X principles of ‘Oh I must wait X amount of time and text one-word answers’. He gave himself fully, in 10 text messages at a time, audio clips, drawings, YouTube playlists. I began to look forward to our many digital conversations, lying in my bedroom glued to my phone.

I’d never met him and I was captivated. I felt like I was getting to know him in such an accelerated way. I felt I already had an intuitive sense of answers to the key questions that it can take ages for us to answer.

Did he care about family? Yes – he was preparing an agenda for his sister’s trip to the US.

Was he sensitive? Yes – one of the most precious messages I have from him is ‘What did you feel?’ Just that one question was so powerful. ‘Feel’. A word so underused by men, but one that cuts to the heart of what many women are about.

Was he chatty? Yes. He sent me a 5 min audio-clip describing the trip he was planning. He was honest with me, and I felt I could then be honest with him and generous with the compliments I was feeling:

“I love how you can talk endlessly” I replied after listening to his audio-clip. This type of appreciative text is a big no-no in the book of Theory X.

“Haha. You got lucky. Normally, I leave 10 min voicemails” he replied.

And so it made me think, why do we so blindly follow Theory X? Does it actually work? Does it actually make you fall for someone if they ignore you, belittle you by indicating you are low in their priority list, show off to you about the awesome happening life they have without you, and express to you how they don’t really need you at all?

Or does it make you fall for someone if they are kind to you, do things for you even though you don’t know each other yet, show their full personality to you, honor you by making an effort, and don’t consult their friends on what to text back but write what they want and when they want?

Concluding thoughts

I’m a new theory Y convert and an optimist again. The thing we have to remember is that it is hard to swim against the current and us Theory Y believers are swimming against the current. So it’s still a numbers game, but we don’t need to pretend to be Theory X, because Theory X believers are not what we’re looking for.

So recently when my friend told me she was really into someone after 2 dates, but didn’t know what to do as he’d become unresponsive, I said ‘Don’t let me tell you what to do. Be bold. Be the most you version of you’. And she texted honestly and boldly asking him in an elegant way about his intentions on their future meetings and expressing she was intrigued by him. And he didn’t reply for a day! I cite this not to exhibit the failure of Theory Y, but to acknowledge that we need to be realistic that it won’t always work because it takes two to tango.

But here’s the observation I want to close on: when you try and you give it your best, and the ambiguity is gone because they don’t reply when you’ve made it clear that you’re interested, you can move on much easier. It is ambiguity, the ‘did he like me?’, ‘could it have worked if I’d tried, if I’d approached him?’ that holds so many of us back. Unanswered questions are lingering thoughts that suck your time and emotional energy. Clear it up, and move on. Save that energy for someone worth it.

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Updates: It did not ‘go anywhere’ with any of the guys mentioned in this blog-post,  but at least the experience wasn’t unpleasant like with the ones who deceive and ghost.

 

 

Dating in San Francisco: The 7 Dates exposé

“The odds are good, but the goods are odd”

said a friend on dating in San Francisco. The testosterone-ridden Silicon Valley has a reputation for a high ratio of men to women, which supposedly would benefit us female folk. My view is that any imbalance between the genders is negative to both men and women. Too many men creates an exoticization of the female species as the mysterious ‘other’ who has to be impressed on dates, mostly with money and talk of how your start-up is part of Y-Combinator. Too many women, as is the case in NYC, leads to another culture where women compete aggressively with each other for men by spending endless hard-earned money on trying to look like Victoria’s secret models, whilst putting out after the first date, when they wouldn’t make that choice if they didn’t feel obliged to.

In this blogpost, I provide a candid exposé of my 7 dates in San Francisco. I cover the good, the bad, and the ugly. My hope is women will relate, and men and women will improve how they date! I did not have journalistic intention when going on these dates, so to protect these men, I will mask their identities as well as possible.  None of these men are even friends of friends so don’t read too deep. I hope no one finds these write-ups offensive, as I’ll go into very controversial topics and be brutally honest about what I was thinking…

Date 1: To inter-racial or not to inter-racial, that is the question

My first date was with a white American guy. Unfortunately, I wasn’t too excited from the photos so I was unenthusiastic and ordinarily dressed as I wandered into this date. We proceeded to get bubble tea and sit in the park. It was a chilly San Francisco evening. He talked about skiing a lot. As a non-skier, I just couldn’t relate to this enthusiasm (I’m probably missing out). I talked about where I grew up, which he found utterly unrelatable (I could tell). He talked about where he worked. It was all nice, but nothing special.

Later, I thought about what was missing. Was it a racial thing? That we’d just had such different lives. Mine has been a quest to prove myself in a world where Indian women are seen as meek and ‘meh’. His was a world where everything seemed smooth and uncomplicated. Could that be it?

I do find white guys alluring, as do many ethnic minority women. There’s something alluring about the privilege we never had, and the confidence centuries of privilege brings. The race issue is a big one in dating, because cultural differences can be significant, and relationships can be hard enough without having two individuals living in two different cultural paradigms. Or is it the case that people are people everywhere and race is just another label which misleads us by pretending it can predict what a person is like but it can’t really? There can be inefficient Germans, punctual Indians and non-stylish Swedish people. The more people I meet from different countries, the more I realize the individual can be anything. My conclusion is to keep an open mind.

Then it got me thinking, if race wasn’t the issue, what makes a conversation special instead of just pleasant and mediocre? I came to the conclusion that 3 main things mattered to me:

1. The person be eccentric, as I am. And talk about strange things, and not be taken aback when I talk about ‘strange’ things (I don’t even count them as strange). It’s always a turn-off to me if a guy is shocked that I want to talk about a parrot that did math whose obituary I read in the Economist. I’m like seriously, you just want me to talk about Game of Thrones, which I don’t even watch?
2. The person be vulnerable. Too many guys show no vulnerability. And I’m left thinking, I guess I must be the only one who is a little lonely being single in the Bay. It’s unrelatable when they present their lives as so complete and perfect with no hint of what they might be striving for because it’s missing right now.
3. The person be passionate about something, preferably a social cause. With this guy, I left the 1.5 hour date having no clue if he actually cared about anything. He described his job as ‘cool’, he liked skiing, he liked Hong Kong. And…so what?

When date #1 and I parted, he thanked me for spending the evening with him (kudos for at least being a decent guy), but we both knew that we’d not be seeing each other again.

• Lesson #1: never be unenthusiastic going in. Dressing without making an effort is bad not just for the guy but for your own confidence.
• Lesson #2: Do not pick a cold or uncomfortable venue. You will then not be able to focus on the conversation. Plus cold makes you shrink into yourself, giving the false appearance of being a less open person.
• Lesson #3: Possibly learn skiing since so many people here love it so much
• Lesson #4: Get clear on what you look for in a person. This has taken me a few dates to establish. But don’t assume that people will have or not have it because of their racial background.

Date #2: The resume talker

Date #2 turned out to be way better looking than his photos (double points for Indian guys who actually work out!). However, in the 1.5 hours coffee that followed, we engaged in resume talk. He talked about investment banking (at least he was honest about how much he had hated it), about his current job at the hedge fund, how the hedge fund has a gym (I could tell). I ended up having a good job interview rehearsal myself too.

He texted me afterwards saying ‘It was good getting coffee. Hope you had a nice dinner!” I wanted a second date, because I felt I hadn’t gotten to know him (and he was hot…), but he never replied to my text back. But I was left with a feeling of respect for him for not just ghosting me. For actually acknowledging that we had spent time together and that it had been pleasant with the basic courtesy of a follow-up text. I wish more guys did that.

• Lesson #1: Try not to ghost? It’s hard with all our massive egos and awkwardness about being direct, but try to treat people like people. Your date is a human with feelings
• Lesson #2: Try to steer the conversation away from resume talk because it is utterly useless to know the resumes of people you will (likely) never see again

Date #3 {Section removed, because we’re on our path to friendship!}

Date #4: The guy who misinterprets feminism

Date #4 made me pay for both of our drinks! We turned up at a bar, and I whipped out my card a little too fast (I get really awkward about paying) to pay for my drink. He proceeded to interpret this as my desire to pay for both of us and said ‘OK great, you get first round, I’ll get the next’. I don’t think on my feet so I agreed. And then we started the date with me already having a negative perception of him as a stingy bastard who didn’t value me.

This guy demonstrated some classical SF dating moves:

1. Talk about things that sound impressive, but aren’t really, in order to be interesting.

Him: “I came across a bear when I was doing the tough-mudder obstacle course.”

Me: “No way! What happened?”

Him: “We had to wait until the authorities moved it out of the way”

Me: “Fascinating”

2. Work on meaningless projects that involve tech, which you think are really cool but anyone with a sense of the problems the world faces would think are lame

Him: “I’m working on this project to connect the lights in my house to the music in my friend’s house, so when they play a song, we get mood lighting in our house and we know they are playing something”.

Me (wine getting to head): “I hear about lots of people doing things like that in SF. Like working on apps to connect fridge to phone. I just don’t get why people work on things like that when there are people starving in the world”.

….So we didn’t see each other again, though he had the nerve to say we should when we said bye. I literally live 10 mins away from him (which he knew) and he didn’t offer to walk me home at 10.30 pm.

Later that week, I lay awake at night thinking about all the injustices women face in the world. How every time we deal with someone who treats us badly, we’re told to brush it off, to forgive and forget. I got really angry, and for women everywhere, I venmo’ed the guy for his share of the drinks bill with the tagline “thanks – awesome date ;)). He completed the request 24 hours later.

• Lesson #1: Don’t let people get away with what you perceive as injustice
• Lesson #2: It doesn’t matter if you’re (politely) honest on the first date when you just don’t agree with someone. If it’s a major difference in life philosophy, it probably won’t work anyway. It’s also a good test of how open-minded you both are to overcoming obstacles. I resolve not to say  ‘Yes. Mhmm’ to things I don’t actually agree with.

Date #5: I learnt about satellites and then never saw him again

He built satellites for a living, and I loved learning about space and the satellite graveyard and all that jazz, over our jazz brunch. He paid despite my offer to split – much appreciated as this was a sore topic after date #4. He very kindly walked me to my next stop (SF Public Library) and then just never texted back! I wasn’t attracted to him, and whilst the satellite conversation was interesting, it wasn’t like ‘omg I must hang out with this guy again’, and so it was the perfect example of the adage that there is very little risk in going on a first date.

 Lesson #1: Just go on the first date, there are some nice guys out there who will enable ‘no-regret’ dates.

Date #6: No comments – as will be seeing him again. Not in love. But he was interesting and nice and warrants further exploration as a friend at least.

Date #7: The one that messes with your head and emotions and makes you remember every break-up you went through though you only had one date with him

Oh boy. This one. 3 hours of drinking and dancing, and an almost-kiss. Some moments of deep connection. And some moments of resentment. These guys are the polar opposite of date #5 (the low risk first date) – they prove that even a first date can be an emotional investment, with significant pain when he doesn’t text back. In anger after the grace period of potential text-back had expired, I deleted ‘The League’ (a dating app) from my phone (I’ve done this 3 times now so it’ll probably be back). I want to reassure people: I did text him first after the date, but he didn’t reply, despite having acted extremely interested throughout the date and referencing future meetings we would have (go figure).

He was fiercely intelligent and witty. But here’s the thing, despite all his charm and supposed wisdom, the guy was 34, was dating Indian girls because his parents would accept them, yet counter to all this marriage-minded logic, I got undertones that he was actually looking to hook-up! E.g., that moment on the dance-floor when he had a look of sheer reminisce on his face and said ‘oh those New York girls. They were something!’. Wah wah wah. When do guys ever grow up? The age seems to move up by 5 years every year.

Or maybe it was something I did or didn’t do (the avoided kiss)? Another sad thing about the dating scene is the lack of transparency and guesswork that we’ve all become so accustomed to. There’s no feedback. It’s a personal preference thing, but I feel I’d be wiser and more at ease knowing why I was rejected.

Lesson #1: A recommendation for my SF engineer friends, can dating apps please build in some feedback mechanism? When someone knows the answer, it shouldn’t be a mystery…or can we perhaps make feedback culture more acceptable? Currently, it is so taboo that when I suggested to my girlfriends that I text date #2 for feedback they were unanimously like “NO, That’s sad, don’t do that!”. Personally, I don’t believe feedback is ever sad, it’s a sign of striving for continuous improvement and having the humility to accept we’re not always perceived the way we intended…so that’s an item on my criteria list: how does a guy feel about feedback?

Lesson #2: Have a mechanism to move on swiftly as these mysterious experiences do happen — the advice my friends give me is to keep myself busy and distracted afterwards

Lesson #3: It’s ok to take a break from dating every now and again. As I’m now going to do after this blogpost!

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The thoughts I’m left with

Every passing day, my appreciation for the deep platonic friendship grows. In friendship there is less jealousy (yes, you may have other friends), more flexibility (you don’t text me in 2 months, I’m still there for you), and most important of all: permanence.

The joy of permanence is so deep. To know that I will look at photos of us together and phone you and tell you I was thinking of you, without ego, without hesitation, because you are my friend.

There is a hidden file of photos on my laptop: smiling photos with a few handsome ex-boyfriends on all of our holidays together. But those travels, like those men, have taken on a temporary quality in my mind. The memories exist but no longer in a collective space where we can both reach them. They exist in my mind only. And I worry some day they will completely disappear, because we never reconnected, or refreshed them, because the small flowers of our friendship were extinguished when our romance was extinguished.

And such are these seven dates of San Francisco such experiences of temporary nature. They are like (mostly) pleasant massages that have no effect as soon as the masseuse breaks contact. Reflecting on why I write so much (my blogposts are a tiny subset of the volumes of journals I have filled over the years), it is this desire for permanence, of freezing moments, thoughts, ideas so that they may last forever. And so I turn these thoughts over to you, my friends and readers, so that we may have good conversations on the themes of life, and so that we may connect again and again and again, and cherish our permanence forever.