April 5, 2011


Modern times have brought almost every imaginable type of human interaction to the digital world--with a host of social media devices available, communication has become nearly inextricable from the Internet. After working in customer support and account management at the site most responsible for this digital trend, Facebook, Jon Budish’s inside scoop planted an idea that given the amount of time people spend on the site “Facebook-stalking” the profiles of their romantic interests, users should be able to connect with their crushes. And so, Jon created iWould, bemoaning: “Over and over, we witnessed people not ask someone out because of the risk of embarrassment from possible rejection...So we decided to try to fix this problem. We sought out to create a safe, easy, and most importantly, private, place to help people get past the awkwardness that is finding out if someone they like, likes them back.” iWould isn’t a dating site--it’s a Facebook application, a “complement to your existing life on Facebook,” explains Jon. After all, if you are already checking out the Facebook profiles of people you like, why not find out if they are checking you out, too?
So if you’re itching to know if your crush likes you back, give the app a try! You might find yourself pleasantly surprised...

How did you come up with the name “iWould”? 
An old girlfriend from college used to always jokingly say it. And then I started saying it...and then I realized that a lot of people say it.

How do you ensure privacy for the site?
Privacy was our biggest concern. We are aware of the sensitivity of the material, and have an extremely talented team of developers who work diligently to secure the information.

What happens once a match has been made?
There are no iWould rules for after a match. iWould is meant to connect people who otherwise weren’t connecting. Once two people know they like each other, hopefully great things happen.

Your ideal first date:
Grab a few drinks, hit up a sporting event or an outdoor concert, followed by dinner.

Your greatest fear:
It’s a tie between tunafish and waking up in the morning and not being excited about what I’m doing. I’ve had some jobs that I hated and it really broke me. I don’t want to wake up in 20 years with any regrets.
Talent you would most like to have: 
I wish I could dunk a basketball.
Accomplishment of which you are most proud: 
I set a goal before I started my MBA that by the time I graduated, I would launch a business. For this reason, iWould is the accomplishment I am most proud of. I’m really excited about iWould, the people I am working with, and the future of the business.

Most important quality in a significant other:
Someone who loves to laugh and is upbeat.

How has technology changed romance?
Technology makes everything easier. Easier does not necessarily mean “better,” but think about it--people couldn’t text 12 years ago. When I was in high school, if I liked a girl, I actually had to call her.

Why is it hard for people to connect in New York?
New York is a big city. People are always really busy and there is definitely a lack of familiarity. It’s hard to date when you are working all the time, so for all you college students--enjoy it while it lasts.

Best date spot in New York City:
I gotta go with Posto. It’s this little gourmet pizza place in Gramercy. The food is incredible, and the place is really charming. Pizza is pretty important to me, so if a girl I’m dating isn’t a fan, that’s probably a bad sign for the future of our relationship.

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