30 Dates

How I Got into Online Dating

September, 22nd 2017

There is a Russian movie, a comedy, called “30 Dates“. I watched it on the flight from San Francisco to Paris last summer. The girl wants her old boyfriend to come back and a video seminar says she will achieve it if she goes on 30 dates. So she signs up on a dating site, and then all the fun stuff happens…

Not exactly the same case. I just always believed I can find a great guy to laugh and share life with without the need of a dating site. I somehow believed it will happen naturally. And now I do not know what “naturally” means. I can’t go asking people at the gym or at work if they are looking to start a relationship, right?

So, I decided I should just do it. Meaning forget how I expected things to be and sign on a dating site and start going out and meeting people. And I did so. Day and a half ago. I signed with Zoosk, because a friend recommended it to me and she had found her boyfriend there.

First things first, the app is completely not user friendly. The design is bulky and I still have trouble navigating through it. But I guess I should not be focusing on the design.

Second, for a person who never was on a dating site before, it is extremely hard to know what to do there and how to act. And I guess any of you who landed on a dating app for the first time would feel this way. It feels awkward. It feels very awkward. I wish there would be a more natural way to meet people. I received about 30 messages within the first 24 hours asking to meet and I did not reply to 29 of them because I did not know what to say, and I was not sure I wanted to meet all these people. And I had no idea what to do if I was not sure. If I reply it will give way to a dialog. Also, men seem nice, and I do not want to be mean and say “no”, thus not replying was the best way so far. Ok, I replied to one of them and he asked to meet this Saturday, and I said ok. I was thinking something like a coffee in the afternoon in the area (and I suggested it), but the guy insisted on inviting me to a night cruise in the bay from 8pm to 12am. And I said “no”. I told him I would be more comfortable grabbing coffee at daytime. He asked if we can plan the cruise for the next week-end. And I just left it there. I am not planning to be stuck on a boat for 4 hours with a person I might dislike during the first 5 minutes. And it is actually even worse for him. He should be careful not to get stuck with me on a  boat in the bay at night, my sense of humor can be disastrous and my chocking gene can prevail.

Third, dear men who are on such sites, please, please, do not post pictures of you and the fish you just fished. I understand that you might be very proud of your fishing skills, but as a main profile picture, when the dead (or almost dead) fish head is as big as yours it looks horrible. Both days I checked the app at night, and seeing this wet fish is disgusting (and yes, it wakes you up ;)). How come at least 20% of men have pictures with fish? Is fish the new black?

Well, pictures are a hard topic. I realized I did not have any or almost any pictures of myself full body in normal clothing. I either had pictures with my kids or pictures in my fighting gear. And I guess pictures are hard for everybody. I finally found one full size from a year ago. These are the pictures I used at the end. Hey, none is blurry!

I never thought I would ever say this, but I will now: I miss Linkedin. Yes, exactly this. Now I realize I love all the pictures of people I know in business. Those pictures and faces are awesome. And absolutely no fish there 😉 I wish Linkedin had an icon / sign that says “open to dating”. This would be so wonderful! I miss seeing intelligent eyes.

Lastly, I am amazed at how few people do martial arts. I know, this is probably not the most common topic when it comes to dating, but I caught myself that on each and every man profile I was scrolling down to see what sports he does hoping to see bjj, wrestling, or mma there, or at least triathlon. None!

The dating app still makes me feel nervous and uncomfortable. However I made a deal with myself that I will go on 30 dates and just give it a chance. And I will blog about it too. With some humor of course. Writing about it should make all this process more bearable. I am sure there should be people like me, who have no idea how to meet somebody, and they have to go on a dating site for the lack of better option. If you are not sure about online dating and want to hear how it goes for others feel free to follow this blog. I promise I will be honest and write how things really were. And it will make you laugh sometimes, or at least smile.

Hacking my Dating Site Profile

September 29th, 2017

After the first week on the dating site I realized the results were not what I wanted. People who contacted me were not the ones I wanted to talk to. Those people who I thought I could have a relationship with never got back on my messages. Bummer.

By that time this post has became quite popular. It got over 4K reads and quite a bit of people contacted me asking for advice or just wondering how dating was going. And my best friend forwarded me this great mocking read on why men post pictures with fish and this awesome TED talk by Amy Webb on hacking online dating.

I have to make a side note here. By now, one week into dating site experience, my interest switched from dating per ce to research and pattern recognition. Understanding human behavior excited me much more than actually hugging or kissing. I wanted to understand the language patterns of online dating, the words used, what phrases get used the most, what compliments, what are the best conversation starters, what “cold” messages got best response rate, and how to become good at it just based on quantifiable and qualifiable data. Yes, I love numbers, linguistics, and spreadsheets!

Since Amy Webb did an amazing job with summarizing the main aspects of what worked in terms of online profile on a dating site, I followed her steps. First of all I changed my profile description. I took all the MMA, business, fighting, and “travel to the end of the world” stuff out of it. I made it just fun, simple, and easy going. And 97 words as she said. According to her research profiles that have 97 well-written words get the most response and attention. I read the profile and I thought I did a good job appearing a lovable, nice, and fun woman. Second were the pictures. As Amy Webb said first put a picture that shows some skin. I did so. I also removed black & white picture (those always get less attention and can even be seen as too intimidating), and of course I got rid of the MMA picture. Then I made sure to include one “family / outdoor” picture and one picture where I am full body with a nice scenery behind (trip picture, Norway to be exact). This is how the new set of pictures looked like:

Guess what? This rational & number approach worked like magic. In a few hours my Zoosk inbox was full of quite interesting messages from men I could see myself meeting and talking to. Once I removed all the work and fighting stuff, the men who actually love work and sports were contacting me and telling me what they do in business and in sports and offering chat, coffee, or glass of wine.

This of course made me even more excited about numbers. I reviewed all the chats and replied to two of them. First one did not go too far, since in the third line the guy asked me what was my intention for the relationship and I had no good answer. So I dropped this conversation for now. The second was a more interesting one. The man did not ask me about my intentions and we just chatted about work, movies, life. For an hour. He was an interesting guy, an industrial engineer working on an relevant problem in a  company that just went public and I could see having a conversation with him. However after one hour he made a few comments how I would get bored with him and kick him out of the house if we lived together. This completely did not enter my mind, I was not planning on living with anybody that fast and these comments made it awkward. From this first chat I found out a few new things about myself & dating:

-I do not know how to flirt (I like talking and laughing, but flirting is not mine). I laugh a lot and I am genuinely interested in the person on the other end. At heart I am a very serious and laughing (and laughable) person.

-Most people tell you compliments because they want to hear the same back. And this does not work for me. I will tell compliments if this is what I feel and I will never do it expecting it to come back. When I sense people tell me that they are drawn to me or that I am pretty with the intention of a “likewise” answer it makes me shut down.

-Even having taken all the MMA and business stuff out of my profile I come across as intimidating. This is the second thing every man I talked to told me.

-I need spreadsheets! I have done a lot of networking for business and spreadsheets worked great for me. I am going to do the same with online dating, because otherwise by the end of the first chat I neither remembered the guy’s name, nor the company he worked for, nor what language he used to express certain ideas. I am starting a spreadsheet with as many common parameters as I can come up with to find patterns of online dating. I want to see if the conversations that start in the same way end in the same way, if by the way people word compliments or flirt I can know what personality they have (yes, I might meet them in person), and if by the type of language people use I can predict if I will have a great time with that person (my language – behavior – results focus). I am interested to see what words people use to describe their feelings, their story, themselves, etc. I will be posting interesting research results here as it goes.

-Lastly, I need to fill the spreadsheet realtime, as I chat. Because Zoosk is extremely slow in retracting the messages. It took me a few minutes to get back to the first line of a one-hour chat to find the name of the guy I was talking to.

To summarize it, the results of the first week on the online dating site were good enough. I learnt how to make the most out of my profile and how to get the conversation started with the men I wanted to talk to. It is also quite tiring (and yes, fish pictures are still there, and I even saw a few lobsters, must be from upper-class guys, just kidding!) and yesterday I took a full day break from it. I had dinner on a parking lot (for the lack of time) with one of my friends and it felt great and we laughed a lot. It was simple and life can’t get better than that.

I think emotions and data do not work too well together. And now I am data driven and I think of the dating site as my data-ing site. I will keep working on it as I’ve committed to the 30 dates and possible pattern findings through language used in online dating interests me a lot.

Date #1

October 4th, 2017

It was nice. I will call him Dave, because his name started with “D”. It was not too awkward. He drove across the bridge and we met for a mid morning coffee not far away from my house. He was smiling and he talked quite a bit. The coffee was very good at this place and I am surprised I did not know about it before, but then there are lots of places I do not know about. So, Dave was a very nice guy, I guess this is the most important thing here.

Before I left the house I decided I will treat it as a business meeting. We will talk about work, and may be coffee, and some small talk. I was working till the moment I had to go through the door and I then came back and put some makeup. If I am going to treat it as business, then I have to treat it as business all the way. High heels, jeans, black shirt, creme jacket, and some makeup (pink and mauve, not the Pirate red #99, which keeps being my favorite and it is for special dates only). It is very warm in fall here. And sunny. I was right on time at the coffee place, but Dave was already there, he cut me when I was ordering my coffee and insisted on it being his treat. Then we talked, first about work, and then more about work (because I like talking work), then he told me about his house, and that it is fully paid for and has a huge yard, and he told me that his story is slightly sad since he imagined he would be married with the family by now. And I think he tried to impress me with some name dropping of famous VCs that he personally knew and showing me pictures of them together. In any case he was warm, sweet, and carried a gentleman air around him. He said he spends his summers in France, 50 miles south of Bordeaux and visits San Sebastian in Spain, he likes it there and wants to keep this lifestyle and just looking for somebody to share it with. And he said would not I like some help in my life and somebody to lean on, and I said I did not want any help. Which is true. (Honestly, this is the first time somebody asks me if I would like some help.) I told Dave that I would like to meet somebody I could love and care for for the rest of my life and spend days together and laugh a lot. He laughed, he said this was different from any other woman he dated or met, all other single moms said how hard it was for them and longed for help. I told him that it is hard, but I like it hard. At the end thanks to all this I am who I am and I will achieve things just because it is all so hard. In a way I am grateful to my ex husband for making it so hard, I would have never become the person I am now if I would have lived in comfort. But then I talk too much…

Dave knew the owners of the cafe really well, he said he came here every day when he used to live in Marin. The owners were sitting behind the bar in the closest to us corner and I had an impression that they were listening to each and every word we said. I noticed their ears turned to our table all the time.

So the date was nice, but I prefer my business meetings to be completely honest. May be I just do not have the right mindset for dating. There is more mystery and hidden future in business chats and in our plans on the pieces of napkins then there was today. There was also certain pressure in the air, like if he expected to see some “romantic” energy from me that I did not have. I was not excited at all. I can keep the conversation up even if I am not excited (like I did on so many networking and business meetings, right?), but on personal level there were no magic, nothing I could dream about at night. He asked for a second date, but I am not sure it will happen. In any case Dave was very very nice.

First 2 Weeks on the Dating Site

October 6th, 2017


This image illustrates how first two weeks on the dating site feel (empty?). Just kidding!

In this post I want to talk about an experiment I am running and some insights in numbers and words.

So, I have spent 2 weeks on a dating site and learning how to make the best out of my profile helped quite a bit to get the conversation started with the people I wanted. I have to say that at the end of the day images weight in much more than words do. So, if you have to prioritize than focus on images and keep the words to the minimum.

Images should be not blurry, relaxed, smiling, face, and full body shots. Images that illustrate your interests are great. It makes you stand out. Do not post images with half of the person chopped. I think eyes on the images are important.

Some numbers from the first two weeks

  • I received a total of 136 messages from men
  • I messaged 15 men myself

What men use for conversation starters

  • 59 Heart icons
  • 21 Smiley faces icons
  • 31 “Hi” (in this category I included any type of “hi / hello / hi there” messages)
  • 25 Short sentences (2-3 sentences to start the conversation)

I had 9 conversations total in these 2 weeks (where the messages were going back and forth on daily basis).

I replied to 2 men out of the 136 that reached out (this means I liked approximately 1.5% of men who contacted me). And I started 7 conversations myself (I reached out to 15 men and 7 replied back).

Here are the conversation starters that worked for me (i.e. that made people get back to me and got the conversation going)

  • Hi! Nice to connect I also live in San Rafael.
  • Hi! Let me know if you want to meet for coffee.
  • Hi! Let me know if you want to grab a coffee some day.
  • Hi! I like your profile. Would you like to meet for coffee?
  • Hi! You have a very interesting face. You seem like a great person to have a conversation with.

What were the main factors for me in replying to men who reached out

  • Proximity (I was not looking to drive more than 10 miles for a date)
  • Face (it should have life in it and I could see we could have a decent conversation)
  • Sports (or activities they do)

I have annotated in a spreadsheet all the phrases that men use to connect, here are the most common ones

  • Hello! How is it going? You have a nice smile.
  • Tell me one of your favorite things you do for fun. Me I like go camping and boating.
  • Nice pictures. Chat sometimes?
  • Hi! I never talked to a super hero before. How are you superwoman? My name is XYZ.

As I noticed about 40% of the cold starters included some reference to physical appearance (beautiful, gorgeous, pretty, smile, looks). Second prominent chunk of first messages played around my dating site name (it is “superwoman” – I did not think about it when I selected the name, but it gave a lot of juice for a conversation starter). Lastly some asked about my interests.

So, men, if any of you are reading this, here are the insights. Hearts and smiley faces do not work as conversation starters. Everybody sends them and they just spam your messages. So, it is a “no”. A nice (may be witty) sentence and a question about interests or favorite things to do on a weekend work much better. Also, do not lower yourself, please. If I am going to date somebody I want the guy to be proud of himself. So, when in the conversation or during the date you say “I like you a lot, but I think you might be bored with me because I am obviously not as smart as you are”…. well, I feel like “what am I doing here if the guy says this right away”.  Right? You are as smart as you say you are on the first date.

Ladies, here is a hint for you: do not sound needy! All the men I talked to said they thought I would be a perfect match for them because I was the first person (or at least first single mom) that did not sound needy or complained about her lot. They all asked for my phone number, date, and pretty much made plans for the future marriage (just kidding, almost) because I was optimistic about life and enjoyed it.

Ok, so by now I was able to scope the language experiment I am running. I am making a bag of words for each men I talked to pre first date. Then I established a few parameters that I score men during the first date (using 1 to 10 scoring system).

Scoring parameters

  • Am I interested in the conversation
  • Kind
  • Intelligent
  • Fun
  • Do I want a second date

On average (in the 9 conversations I had up till now) each man had wrote close to 200 content words. The clusters of words that are repeated multiple times differ from one man to another. And I am starting to get the sense of the person based on the words they use (the repetitions and also “extreme” words). If you think about it 200 content words is not that much, so you set your image based on these 200 words, and using “extreme” or interesting words definitely gives you a flavor. By “extreme” I mean not typical words that everybody uses. By now I can divide the 200 bag of words of each man into 3 parts

  • repeated words (these I think are related to one’s emotional state and personality)
  • common words (that almost all men use and here the bags of words overlap)
  • extreme words (these are the ones that set the person aside and signal about one’s intelligence and interests)

I need to get more data to be able to present a better study and insights. I think it is becoming quite interesting.

Date #2

October 8th, 2017

It was inspiring, and full of content, and interesting. We grabbed a glass of wine on the deck of a restaurant overseeing the beach in Sausalito and we ended up talking for two hours. The guy was quite interesting, of Sicilian origins, he had to fight (literally, kickboxing & street fights) for years to pay his way through college. He told me the stories of his childhood and his life now. He built his life all the way from the ground up and achieved a lot in this corner of the world. He seemed human and honest, survivor who made it through life. And we both agreed that laughing together was very important in any relationship. However, even though I smiled a lot, I did not manage to laugh. May be it takes some time to be able to laugh together with somebody.

He wore a very strong perfume and the smell made me dizzy and this made me doubt all his words. I could not shake off the feeling that everything was somewhat a lie. May be it was just the smell, because I do not like any artificial smells on the skin. I actually enjoy the natural skin smell of each person I meet. Once I told a friend that I think I understand people through the skin. It is as if my skin “spoke” to their skin and I got right away all the important notions about the person. With the strong smell covering the natural smell I was completely disoriented and everything seemed not true.

I was so not myself that I forgot to look at his ears and see if those were the fighter ears (as a fighter you normally get cauliflower ears). And I also forgot to ask his name.

When we said good-bye he tried to give me a kiss, but I made it a hug. I do not want to kiss somebody just because I might. I want to enjoy it too, and I would not have enjoyed this one.

In the car I only could smell his perfume (it seemed glued to my sweater and neck). The smell grew very strong and I felt empty and all I wanted was to get home, change clothing, and take a long bath to take this smell off my skin. And so I did.

Date #3

October 20th, 2017


We were texting for a few weeks before we met. Better to say, he was very attentive texting me and asking about my likes, tastes, preferences. I tried to follow up with replies, but I mostly failed. My jobs took the best part of me and my replies were sporadic to say the least.

We met for a morning coffee in one of my favorite places in Sausalito. He came a little bit earlier. He was Indian, and this is one of the reasons I wanted to meet him. I wanted to hear his story, I almost never tried to date an Indian before. From the very beginning he was very considerate and respectful. This made the conversation flow. Unlike my other dates he started by saying that he does not want me to feel awkward or pressed to talk to him, and if I had to leave at any moment it was totally fine. And if we just meet like friends or business partners it would be totally fine as well. Then he handed me a package he had in has hands, it was a nicely wrapped large box of dark chocolates, exactly the ones I liked. Now it made sense why he was asking about my tastes in desserts. The truth I was very touched by this gesture.

We had coffee and we talked a lot about work. And it was like a good business meeting and I actually felt at ease and I liked talking to him and he offered to help with my company. He was a software engineer who moved to business growth in the last 10 years, but still worked a lot with the developers. He seemed genuinely interested in what I was doing. And I had a sensation that he was kind, humble, and considerate. He told me how he lived in Canada for five years before moving to US, and the companies he worked for, and that he never managed to say two words in French despite having lived in Canada.

He accompanied me to the car. And everything was calm, and I put the large box with chocolates in the back of the car. And at home I did not want to take it out of the car and bring it home. So the box stayed in car till I went to pick up the kids from school. The kids saw the box and asked about it. And I told them that a coworker gave it to me. And my daughter asked, “Is it because Christmas is coming?”. And I said, “Probably”. And we took the box home.