Those First Dates!

Editor’s note: Jess Roe is a photo editor at Zulily where she creates beautiful visual experience that makes Zulily's product detail pages stylish. In this article, Jess talks about her experiences with the first dates she had over past couple of years!

So I have to admit, over the last couple of years I've done my fair share of online dating. I’ve had a bit of success, but I’ve also been on loads of first dates, that never seem to materialize into much more than that. When I sit down and reflect back on a lot of these first dates (and even second dates), I’ve realized there’s definitely some themes that have influenced whether I accepted a second date or not. If I had to sum it all up, what I’m looking for on a first date is a guy who can actually plan a date, who exhibits some form of manners (crazy right?), and carries himself with a positive air/confidence.

This first topic I always find a bit funny, and have had some interesting debates about, with friends - and that’s a guy who can actually plan a date! Maybe I’m a bit old fashioned, but on a first date there’s something fun about being “taken” out. It feels nice when you've invested some effort into impressing me with your plans. Even if I plan every date from now on, it’s nice to know you can coordinate, and make it happen. If planning isn’t your forte, just by asking some simple questions…my favorite restaurant, the nights I’m free…you can still easily make it happen! 

All right, now on to the actual date! Manners were huge in my family growing up, and definitely something I pay attention to, and look for in someone else! While it’s easy to be nervous and self-conscious, I would hope you would still revert to your basic social skills when on a first date. I don’t need you running around, opening every door, or going over the top, but a little please and thank you, goes a long way. Another biggie is how you treat the wait staff. It’s always a major turn off on a date when the guy can’t make small talk and have fun with a waiter. I know you’re here to interact with me, but I also care about how you interact with others you encounter in your life. When you’re acting like you’re above the wait staff, I can’t help but wonder how you’d treat the other people in life – my friends and my family – this is important to me. 

Going along with character, I’ve found a person’s tone can be a major turn off on a first date as well. The way you talk about your friends, family, work and hobbies reflect a lot about the meaning and value you place on these different topics.  To me a first date is all about sharing and getting to know what makes another person tick. If you’re talking negatively about your family, or your job, it’s definitely a red flag and not enjoyable. I don’t know about you, but I can’t remember that last time I got excited to date someone who didn’t respect their family, hated their job, and had no passions in life. I get it, bad days happen, and sometimes work sucks, but I don’t need to hear about it on a first date!  

With all of this said, I never like to approach dating with a checklist, well maybe I should say a hard and fast one. I always get annoyed when I receive emails from guys getting upset about an attribute I’ve mentioned in my profile as being highly important in the person I date. I know the qualities I’m looking for, and don’t feel I should be judged or have to compromise what these are. While the above mentioned categories are not make or break, being able to plan, having good manners, and a positive attitude on life are important qualities that I value, and for me influence whether I want to continue dating another person. 

Truffle's YC Application

What is your company going to make? 

Truffle is a mobile dating web app that is geared towards providing a beautiful dating experience to a working professional. Every 3 days, I open on my browser and get 3 matches from a designer at Zulily to a Sales Manager at Amazon. I invite the designer at Zulily for a coffee and that's it. I have a date.

There is no online messaging. Trust among the Truffle users is established by only allowing people in your same class i.e having similar educational and work background. You either sign up via linkedIn or you need to have an access code given by us.

For each founder, please list: YC username; name; age; year of graduation, school, degree and subject for each degree; email address; personal url, github url, facebook id, twitter id; employer and title (if any) at last job before this startup. Put unfinished degrees in parens. List the main contact first. Separate founders with blank lines. Put an asterisk before the name of anyone not able to move to the Bay Area.

pacifi30; Nishant Singh; 29; 2009; Arizona State University; Masters of Science in Computer Science;;;; nishant.singh; @nsingh28; SDE at Amazon.

sunshineo; Gordon Sun; 30; 2008; University Of Toronto; Bachelor's of Science in Computer Science;; n/a;; gordon.sun.14; @sunshineo; SDE at Amazon.

agathayu; Agatha Yu; 21; 2013, University of Sydney, (Double Degree in Bachelor of Commerce (Finance) and Law);;, n/a, im.agatha, @yuagatha; Designer at Palantir.

chenyuwang1988; Chenyu Wang; 25; 2012 June, University of Minnesota, Twin Cities; Master of Science;; n/a;;; n/a;  SDE at Amazon

Please tell us in one or two sentences about the most impressive thing other than this startup that each founder has built or achieved

Nishant: Until the age of 23, I had a bad stammer. The combination of moving to a new country, getting scholarship at ASU, dressing well, and working harder to achieve my goals, gave me the confidence I lacked. Consequently, with my effort and luck, now I give speeches at Amazon. To help others overcome this problem, I also run the Seattle Stuttering group.

Gordon : I was a regional champion of Physics Olympiad Competition in junior high. While at IMDB, I built new ranking system where I reduced the rank generation time from 10 hours to 1 hour using Hadoop and Amazon Elastic Map Reduce.

Chenyu : I was a fat little boy and failed all the sports exams. The summer before high school I decided to learn breakdance, I exercised night and day. Within 3 months, I won the school's dance competition and started my own dancing club. I also became the president of the Art and Performance department at the student union.

Agatha: I was among the 0.1 percentile of the high school graduating class in Australia, and was awarded a full scholarship for law school. I also designed the sales tool interaction for Australia's national telecommunication company, yes I had to go through a lot of approvals for my design.

Please tell us about the time you, pacifi30, most successfully hacked some (non-computer) system to your advantage

I wanted to advertise Truffle on LinkedIn, but the ad got rejected on the grounds that LinkedIn doesn't advertise dating sites. I tweeted Jeff Weiner, CEO of LinkedIn, about the rejection, and the next morning the ad was approved.  

Please tell us about an interesting project, preferably outside of class or work, that two or more of you created together. Include urls if possible

Gordon and I(Nishant) created Suppermate, a mobile app for dining with your friends of friends. We organized 98 dinners in Seattle over the period of 2 months.  

How long have the founders known one another and how did you meet? Have any of the founders not met in person?

I(Nishant) met Gordon through a mutual friend in 2010 and since then we have been coding on side projects. Gordon created the necessary infrastructure enabling us to easily integrate new features.

I(Nishant) met Agatha at YC School reception in Oct 2012. She got so excited by the idea of an exclusive dating app for people like her that she designed the landing page for Truffle next morning. From the first design to bringing in the women perspective in Truffle, Agatha has become one of the pillars of Truffle.    

Gordon and Chenyu have worked together at Amazon since 2012. Gordon introduced me to Chenyu in Jan 13. Ever since Chenyu has not only been an intensely driven dev for us, he also comes up with creative marketing channels like distributing Truffle access cards through food trucks.

Why did you pick this idea to work on? Do you have domain expertise in this area? How do you know people need what you're making?

Love excites me! It excites me to see two people holding hands and walking down the Broadway Ave. I want to spread love, so I built Truffle, and opened it for all the working professionals ready to fall in love.

I moved to Seattle in 2010 and I found it difficult to meet girls. I tried okCupid, and often I would end up sending tens of messages before getting a response. Even after connecting online, it was still a challenge to meet in person because conversations would just die.

I spend hours surfing online dating websites, tried things like including work/education info in my dating profiles and send straight forward coffee request messages to girls. Eventually, I was able to meet 30 girls from okCupid, eharmony over the period of 3 years but only ended up dating 2 of them primarily because one of my criteria was to date someone who had a similar education and work background to my own.

The idea of Truffle came to mind when most of the girls I met liked the straight forward meeting at cafe approach I took and insisted that they agreed to meet me because I worked at a good company and looked presentable.    

We talked to over 150 people who have used or are using eHarmony and Over 60% girls responded that they don't trust the men and have fear of getting stalked. Whereas an overwhelming 77% of the guys complained about the delay in getting an in person date. 43% of the people feel that they are paying $53 a month just to look at the image catalogue because rate of landing a date is low. 20% out of 280 users on Truffle are from okCupid, eHarmony and

Working at Amazon also gave us an opportunity to talk to other amazonians and out of 200 singles in the age group of 23 - 29 we talked to, 80% of people will like to go on a coffee date with someone they have seen at the amazon campus.

We have organized 63 dates since we launched so people are liking it.

What's new about what you're making? What substitutes do people resort to because it doesn't exist yet (or they don't know about it)

We offer four novel things

1. Exclusive user base of working professionals.

2. Per date pricing.

3. No messaging online to encourage users to communicate in person.

4. A new experience. Instead of a message about "How you doing", you get an invitation for a coffee date.

Currently, 33% of people using traditional online dating loose hope and close their account. People tend to have the following pattern in the use of existing dating services.

1. People tends to start with eharmony and but no face to face dates lead them to the location based apps.

2. Location based apps like Tinder are quick but are more of a fun game then finding someone you may want to develop a relationship with. After a couple of matches with 18 somethings, our target audience drop off.

3. Lastly, people resort back to look around for potential partners in their friend circle that is first of all small and second doesn't give them the opportunity to meet new people.

Who are your competitors, and who might become competitors? Who do you fear most?

There is a tiered hierarchy of dating apps

1. and eHarmony : These services provide a poor quality of dating experience that usually make people quit or inactive on these platforms. Over that, the high subscription cost with no results make it even harder to trust these platforms.

2. okCupid : Users have range of options and a free communication online platform. However, the conversations online don't lead to anything meaningful.

3. Tinder:  This is more of a fun way to gauge your hotness meter. People like each other but only few take it to next level and go on a date. Tinder is tailored towards to teenagers and college students.

Companies like Vice and the subreddit like r/singles can become competitors since people on these communities have similar interests and tastes. Grouper shares our DNA as they facilitate offline meetup. One day if they decide to start organizing one on one dates, they will be a threat to us.

What do you understand about your business that other companies in it just don't get?

80% of what happens on a dating site is ineffective. No filter on the quality of the people as well as the online messaging creates too much noise.

I don’t need to know which movies you like or what food you eat when I want to meet you the first time. If you are good looking and we are in the same class, everything after that needs to happen face to face. The decade old model of writing about yourself in 1500 words and answering 100 questions to test the compatibility does not guarantee a meet up or a relationship. Instead focussing on meeting first and then asking questions to each other have a higher chance of successful companionship.  

Moreover, the primary purpose of online dating is to meet someone in person who is not in your social circle but “can” be a part of your circle. And the way you extend your social circle is when you get an invitation to a house party from your co-worker and not by answering questions about if I currently like dogs or cats.

At Truffle, we are opening this window of opportunity to date the person you have seen in the elevator during lunch hours. On other dating websites, you get a “how you doing” email message but on Truffle you get an invitation for a real date at a cafe at a particular day/time.

How do or will you make money? How much could you make? (We realize you can't know precisely, but give your best estimate.)

#Singles/2 * #dates per month per user * cost per date

[Usually men ask out, hence /2]

According to harmony numbers, out of 20 million singles, 14 million users earn 50k and above. and okCupid have a total of 29 million singles out of which 10 million are working professionals and earn above 50k.

Total user base for Truffle in US = 24 million

Average number of dates per month = 10

Cost per date = $10

Net singles market = 24/2*10*10 = $1.2 billion

We will also provide boutique packages for the "couples" who want to take their relationship to the next level.

#Couples/2 * #packages per month * commission on each package

Number of successful date packages per month per person= 5

Average Commission per package = 20%

Average value of the package = $100

Net couples market = 24/2*5*20 = $1.2 billion

Total addressable market = $2.4 billion

If you've already started working on it, how long have you been working and how many lines of code (if applicable) have you written?

We started working on Truffle in September 2012. We wasted 2 months of our time by building a phone gap application that had latency issues so in Nov 2012, we started building Truffle website and as of now have written 90k lines of python, html and jquery code. We have deployed our code 548 times on the development and 152 times on the production server.

How far along are you? Do you have a beta yet? If not, when will you? Are you launched? If so, how many users do you have? Do you have revenue? If so, how much? If you're launched, what is your monthly growth rate (in users or revenue or both)?

We launched Truffle in May 2013 for Seattle and have 280 users based in Seattle and 100 users outside of Seattle. We have organized 63 dates with the gross revenue of $190 (we gave away most of the first dates free to our first adopters)

Our user growth is 25% in each of the last 3 months.

If you have an online demo, what's the url? (Please don't password protect it; just use an obscure url.)

We have video that shows Truffle user experience

Also this is the URL for our demo App (It might take some time to load the app since its running on free heroku instance that remains idle if there is no activity )

Things to try:

* Sign up via LinkedIn and select your city as Seattle

* Click on one of the matches and ask them out

* Credit card details are already provided

* Choose a date and place. You have sent a date invitation

* I ll accept the date and we can have a coffee in Seattle :)

How will you get users? If your idea is the type that faces a chicken-and-egg problem in the sense that it won't be attractive to users till it has a lot of users (e.g. a marketplace, a dating site, an ad network), how will you overcome that?

We know our user base is concentrated in hubs like South lake union in Seattle to Soma in SF. We used guerrilla marketing and hired taskrabbiters to give priority access cards to our target users located in SLU in Seattle. Average cost of acquisition is around $2 per user.

We also run promotions with the businesses near these hubs. Food trucks are our primary distribution channel at this moment since they visit the dense neighborhoods during lunch hours. Average cost of acquisition is $5.

Our recent targeted advertising on Facebook gave us an acquisition cost of $10 per user.

Also from the start we have advertised Truffle on our okCupid and profiles. So far we have successfully converted 57 "other" dating service users into Trufflers.

If you had any other ideas you considered applying with, please list them. One may be something we've been waiting for. Often when we fund people it's to do something they list here and not in the main application

Batch Dinner Delivery : Finding quick and cheap dinner is a challenge for single people. I don’t have time either to cook or sit at a restaurant every day or do an expensive delivery. I would love a service that everyday at 2PM messages me the one dish they can deliver at 7PM for $10 at my neighborhood. By making a huge batch of orders for a single dish and delivering at once to a neighborhood, it is possible to reduce the cost of delivery. Other benefits includes better inventory planning for restaurants because of the order ahead capability as well as making the location of the restaurant irrelevant since any restaurant will be able to deliver it's food in bulk to a far off neighborhood.

Calmix : An Outlook like scheduling assistant that gives the invitor a preview to invitee's availability even when they have different exchange email servers or different calendar clients or the invitor doesn't even have a calendar. We want to use this service for giving matches on Truffle based on the availability and location.

Octave: A mobile app that teaches singing with a set of minigames. Grow as a singer while pursuing achievements in those games, and connect and share with other singers.

Please tell us something surprising or amusing that one of you has discovered. (The answer need not be related to your project.)

I have discovered an elegant way of cutting an avocado.

Keep it Simple

Some companies do one thing and they do it right.

Southwest Airlines use only Boeing 737s

Apple has historically tightly controlled it's product line up.

These companies are profitable not just because they offer fewer choices but internally they have to maintain even fewer processes.   

You have Boeing 737, you just need to train your engineers on one model of Boeing. You save maintenance cost in the long run.

You have distinguishable product lines, people have less confusion. Less confusion drives product sales. 

At Truffle, we have a mantra and we call it "Start with a coffee".  Below are few things that we have gained by following our strict do one thing and do it right policy.

We only have to choose cafes as our meeting spots. Save time for us in establishing relationship with businesses. 

Coffee is light weight. It help us in lowering down the barrier for an in person meetup.

There is only one action to take on Truffle

You like someone, you ask her/him for a coffee.

All it takes is a coffee.

Truffle-ized are we?

Editor’s note: Nipun is the Truffle's PR guy, he is the one who tells heartfelt stories about Truffle to the world. In this article, Nipun talks about his experiences with two of our users.

Have you been Truffle-ized yet? Hearing these words at Café Ladro in Queen Anne made me smile and brought a sense of proudness regarding Truffle. After all, how often is it you run into your users who just love the concept and are willingly beating the drums of success. I just couldn’t stop myself and introduced myself to two friends Marie and Ashley who were having a conversation about Truffle. 

Marie mentioned she had been using Truffle for about two weeks and has already met 2 people during this timeframe. She mentioned that Truffle made her life really easy by allowing her to talk with people she liked in-person. She also complemented on the fact that Truffle partners with well known local cafes (known as Truffle meet-up spots), which provided a sense of safety, especially when meeting someone for the first time.  

I brought this feedback to the Truffle team and they were filled with joy. After all, Truffle is about connecting people and we made it happen! This incident led us to survey Truffle customers who are also part of sites like and to determine how often are they meeting people in-person.  What we found was a head-turner. Truffle users have about a 55% higher chance of meeting someone in person in the first attempt compared to leading online dating sites. Not only they have a higher chance to meet, they save 100% of the time creating and perfecting their profiles. You just upload the picture of who you are and you are done!

So folks, let’s take an oath. “I’ll not waste my time in the virtual world, I’ll rather go out and meet people” Let me be Truffle-ized!

Break the pattern

Wake up, gym, shower, cereals, walk, amazon, sit, lunch, feature, complete, production, walk, home, cafe, truffle, talk, smile, home, reddit, sleep 

And I have been repeating the above cycle every day for the past 3 years

Woke up today, looked outside, and the weather was awesome.

Decided to take a day off from Amazon.

Thought of working on truffle at Cafe Ladro (I love their Lattes)

So with my thoughts I started walking down to the cafe via Seattle Center... saw the fountain, sat down on a bench. Couple of things happened.

- Seattle Center Fountain is beautiful

- Seattle center has free wifi so you can sit anywhere and work

- Small small kids are so darn cute

- People from Dubai have an amazing american accent.

- A mom of 4 kids can seriously multitask. Feeding, towels, kisses, love, phone, happy.

From time to time we need to break away from our day to day lives and just enjoy our surroundings. I am not sure if I learnt anything from this detour but one thing is for sure I am happy.

Break away from online dating - meet someone in person!

Truffle will revolutionize Dating!

In today’s world where everything from groceries to car shopping is done online, it has become difficult to connect and meet with other people. This has given birth to online dating, which has bridged the gap by providing a mechanism for people to virtually connect with other potential singles. As a result, folks on sites like, eHarmony, etc spend countless hours messaging other singles, hoping to get an in-person date. They write and re-write their profiles, just to get the other person’s attention.  This is exactly where Truffle is making a difference and changing the paradigm. 

Truffle is a boutique dating website targeting working professionals who want to meet and connect with other singles in-person instead virtually. It is built on the fundamentals of reducing the time it takes to meet that someone special. It works on three simple principles:

  1. Confirm you are a working professional via LinkedIn authentication

  2. Upload pictures that tell the world who you are.

  3. Go ask that special someone out for coffee.

There is no “about me” to be written. No profile telling others why someone should pick you. Everything is communicated through pictures. After all, a picture is worth a thousand words!

Behind the scenes, each Truffler is given three matches every three days. Once one Truffler likes another, he/she can ask him/her out. If the other person accepts, the inviter pays $10, there is no recurring subscription charge. Upon date acceptance, Truffle provides six local coffee shops where both the people can meet over coffee. These coffee shops have been hand picked to ensure the meet-up experience is as smooth and safe as possible.

So for all the single folks out there, try Truffle ( and Start something lovely!

Dating through meeting

Editor’s note: Jess Roe is a photo editor at Zulily where she creates beautiful visual experience that makes Zulily's product detail pages stylish. In this article, Jess talks about her experiences with online dating and list some of her concerns in the current online dating model.

Ask any of my friends; my biggest pet peeve with online dating is talking to a guy who wants to chitchat, but never pulls the trigger of meeting in person. You know a few emails are great to establish a connection, but when it gets to the point of sharing one’s whole life, emailing just doesn't help! You got to meet face to face to express your true self.

I was thinking about it the other day, all great or meaningful relationships in my life have always started out slowly. You meet someone new, they seem cool, you have a few things in common, and you hang out. It’s not usually instantaneous with sparks flying and fireworks going off. However, it’s through shared experiences, inside jokes, and time, that you begin to realize the depth of another person. 

I’m guilty of approaching online dating the opposite way. I create this vision in my mind of the guy I’m expecting to meet, and if he doesn't match what I'm "looking" for after the first date, it’s easy to move on to the next guy. We end up screwing ourselves over with our preconceived notion that we’re instantly going to hit it off with this person we think we already know.

I think a lot of this has come from the misconception that it’s bad to date more than one person. Dating shouldn’t be treated like an audition; it should be seen as an opportunity to gain a deeper understanding of another person. Online dating needs to less about sitting behind your computer and more about interacting, getting to know each other, and allowing a new relationship to form. Take a risk; you never know when you might hit it off with someone.

Let's start a conversation at a coffee shop and take it further

I love coffee shops. I've made many friends, got introduced to my marketing wizard through a barista and most important of all, I met my girlfriend at a coffee shop. The love of coffee shops is probably the reason behind our tag line at Truffle - We make 2 people meet over a cup of coffee.

Anyhow, below is first of the series of stories where I'll talk about how I took a conversation at the coffee shop further. 

Flash back to June last year!

I like this girl sitting at a table beside me and she seemed to be talking about startups with couple of people. Interestingly, she seemed to have started her own.

I have got a lethal point to start the conversation.

I am waiting till she is done with her conversation. Finally after an hour, they started leaving. Coincidently, she is the last one to leave.

5 second rule! If you don't act now, you'll never get to talk to her.

I ask "Hey, do you own a startup?"

I said "own" not "work"!

She said "Yeah, do you as well?"

Have your pitch ready. After the pitch, make sure you ask a follow-up question about your startup.

I told her about Truffle and asked what she thought of offline dating. We chatted for about 10 mins.

Evolve a habit of asking questions. It doesn't just help with girls but in general will make you an interesting person to talk to.

Turns out she has a boyfriend! That's ok, I got to meet a new person. We exchanged emails and went our ways. We ran into each other a couple of times later at the same coffee shop. 

Try to make one coffee shop your base. People will recognize that you are a regular and remember you.

After some months, I  asked her about getting dinner sometime in the next week.

Always have a place/time ready when you invite someone for a meeting. Decisive people usually end up with more dates.

Don't even think about flirting on your first meeting. First, you are breaking the bro-code (she has a boyfriend) and second it will just put her off. 

Ask her if you can walk her home. Gather some gentleman points.

During one of our conversations, she brought a new startup idea she was thinking of, I extended my help.

Whether it's a girl or a guy, helping fellow entrepreneurs is always a sweet thing.

So things took a wide turn and she had a break up. I didn't know about it until she told me at a dinner that I invited her to, with my friends. 

Pro point : Always good to include new friends if you are having dinner with your older friends.

After about a week from then, I asked her out for a dinner again, without the friends. She said yes and I guess that was our first date.

I said guess because I was not sure if it was a date but I'll tell the other half of the story in the next post soon. Oh, and if you are reading this article in a coffee shop, go ahead... start a conversation with the person sitting beside you.  

Truffle Your first coffee date is on us :) 

Our first $10

March 22 - 2013, I for the first time understood the importance of 10$. 

We launched Truffle in Seattle in March. 

100 users signed up, 10 date invitations were extended. 

Every day, I used to log in admin mode to see if there was any accepted dates.

By the way, every accepted date, Truffle charges the initiator $10.

I woke up one morning and went directly to Stripe.

Hold and behold, Stripe dashboard was showing a sparkling $9.41 as the "next transfer".

I think all I remember was that I jumped off my bed and called Gordon/Agatha/Chenyu (Truffle co-founders). Pretty sure all they hear was 10$ and nothing else but I guess they realized what I was saying. 

10$ is nothing. Even a lunch in Seattle cost around 11$ plus taxes. 

So why was I so happy

0. Someone bought our vision.

1. Don't know why but it felt as if these $10 > amazon salary


Truffle ( is simple dating platform for working professionals. Come start something lovely with Truffle.