Be Your Best Self Connect Date Ideas Lifestyle Trending Vina Users


Here's information on the booming demand for matchmakers and expert dating advice from Professional Matchmaker, Sasha Silberberg.

In a world where Cupid can be found right at our fingertips, we swipe right hoping to find “Mister-or-Misses-Right.” However, while dating apps have made much success over the last decade, for some singles, the match just isn’t made as easily. That’s when we turn to a real-life Cupid: a matchmaker.

VINAZINE sat down with dating coach and matchmaker genius Sasha Silberberg, Founder of OkSasha—a dating website known to “spread love like butter”—to delve into what it takes to find people’s right matches and how to navigate the dating world!

Q: Thanks for talking to VINAZINE! What inspired you to become a professional matchmaker, and what is it like owning your own matchmaking business?
A: What inspired me to be a matchmaker was a slew of factors. The loneliness epidemic, our lack of community and online dating leave a lot to be desired. I noticed that a lot of people were tired of online dating, and there aren’t many great alternatives out there. I started working for a matchmaking company called Dating Ring back in the day, which propelled me into the world of matchmaking. After working there for about a year, I realized that I could have my own business and do matchmaking my own way. From there, I started working with clients one-on-one on my own while also driving for Lyft. I used Lyft as an opportunity to meet new people and get them into my “match book.”

Running your own matchmaking business is a lot of fun and work! Getting started by building a big network is certainly a task—you need to know a lot of people and earn trust. Then, there’s the business side of it: accounting, creating a website, marketing, etc. Living as an entrepreneur can be challenging because you must be self-motivated, waking up every day and pushing yourself to do the work.

Q: What type of clients do you normally find yourself working with?
A: I work with people in Silicon Valley between the ages of 25 and 40. Most of the people I work with work in tech and are at least tangentially part of the Burning Man scene. They’re all successful in their work and relatively busy.


Q: What makes your matchmaking techniques different from other similar businesses?
A: My matchmaking technique is different from other matchmaking businesses in the sense that it is community-oriented. What that means is, whenever I take on a new client, I interview one or two of their close friends/family members so I can have an idea of who the client is in their community. Chatting with close friends and family also often unveils some of the clients’ blind spots in dating, which is clearly very helpful!

Q: Now for our single vinas who are craving that real-life connection, this one goes out to you! Do you have any dating advice for us?!
A: When you go on a first date, actively try to keep an open heart and mind. Just because you don’t feel an instant connection doesn’t mean that this person can’t be an important part of your life. You can learn something from everyone, and who knows, maybe they are best friends with the love of your life!

Also, try to be aware of the subtle nuances in communication. What I mean by this is that we often times put people into boxes without knowing it. We think that we are excellent at judging people by talking to them for five minutes, but we fail to acknowledge all of the other factors that are coming into play during a first date. For example, maybe they’re nervous, or maybe they’re hungry, or maybe they misheard or misunderstood what you said and therefore said something to you that wasn’t actually representative of their character. Just remember, you WILL fit someone into the box you create for them.

Q: Speaking of all this matchmaking, what do you think about the Hey! VINA app, the Tinder for finding your best (girl) friends?
A: I’m totally a fan—the loneliness epidemic is real, so anything that builds community is desperately needed!

Sasha reminds us that love is always in the air for those who are willing to keep their hearts held high and a true belief in real-life Cupids. Happy dating, vinas!

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Love, friendships and life-long connections can be created anywhere, but luckily you’re here at Hey! VINA so you might as well start swiping!

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