We're kicking off a series of interviews with some of our favorite San Francisco Bay Area matchmaker partners. Our first matchmaker, Sasha Silberberg, is the founder of OkSasha, a matchmaking firm for singles in their 20s, 30s, and early 40s in the Bay area.
We love Sasha's creativity - for example, she hosts a unique dating event called "Dating in the Dark", which is exactly what it sounds like - dating while blindfolded. While not for the faint-of-heart, it's an experience that allows for more genuine connections between participants. Learn more about Sasha's matchmaking philosophy below.
Interview has been edited and condensed for clarity
Tell us about yourself
I grew up in Washington, D.C., and studied public health in college. I moved to San Francisco to be closer to my sister and ended up living in a series of community houses including an ex-nunnery with 24 people. Now I live with two other female entrepreneurs and spend my days connecting people!
Why did you get into matchmaking?
I believe in the importance of community and loved what those houses represented, so I wanted my work to reflect that. I happened to meet Courteney Kay, who is a matchmaker and who has become a mentor of mine. Through her, I started matchmaking at the Dating Ring, and then decided to leave and start my own matchmaking business because I saw lots of room for innovation.
When I first started, I was also working two other jobs – one as a Lyft driver and one as a caterer. I decorated my Lyft car with hearts and glitter and would invite riders to join my “Match Book”. One day, a San Francisco Chronicle reporter got into my car and wanted to write a piece about me. I now do matchmaking full-time and have continued to build my network through local and national publicity as well as word-of-mouth.
What is your matchmaking philosophy?
I am very community oriented. I put a lot of weight into who you surround yourself with. With my new clients, I interview two of their friends as part of the process. I don’t know any other matchmaker who does that. I also often end up becoming close friends with clients. In this industry, there’s a fine line between work and your social life, and although some people may disagree, I believe becoming close to my clients allows me to truly understand them. I typically have about 6 to 10 clients at once, and they are men & women between the ages of 25-40.
On to photos. Why are good photos so important?
Photos are essential! They are the most important part of any online dating profile. They’re obviously more important on short-form sites like Bumble and Tinder, since you’re first swiping through photos, then seeing profiles. On long-form sites like OkCupid, they’re slightly less important, but still pretty important!
Humans are very visual and physical people, and photos can make or break your profile. When I show clients photos of potential matches, the photos sometimes aren’t that great (as compared to how the match looks in real life). Not everyone is photogenic, and sometimes I’ll come across people who barely have one picture of themselves. In these cases, I have to tell my clients to trust me and just go on the date, and inevitably I’m proven right. But most people don’t have me there to defend them! They just have a bad photo!
What are your dating photo "dos"?
You want to have a set of photos that is representative of your personality. What’s going to get someone interested in you is a photo that makes the person feel connected to you; one that elicits an emotional response from them. Make sure your main picture is the best picture that you have - it can be a headshot or body shot, but it should be an attractive photo of you that creates curiosity. You don’t have to have a photo of you climbing Mt. Kilimanjaro, but don’t just have a photo of you standing in front of a lake! You should also have a variety of photos so a potential match can look at them and envision themselves with you in different situations.
"What’s going to get someone interested in you is a photo that makes the person feel connected to you; one that elicits an emotional response from them"
What are your dating photo "don'ts"?
I have two of them. One is sunglasses! Do not wear sunglasses. That is one of my biggest pet peeves, because you can’t see the person’s face. I want to see your face! If you have a sunglass photo, it better be extremely interesting and say a lot about your personality.
The second is for men – please, no photos with fish! I don’t understand why you have a photo with a fish you caught. This is not the hunter-gatherer era in America, especially in the Bay Area. Please do not show me a dead fish in your photo.
What is a piece of advice for someone just entering the dating pool?
I have two pieces of advice for Bay Area men. The first is that you need to use your friends to help you with your dating life. I read a statistic that something like 20% of people show their dating profiles to their friends, and of those 20%, only 30% are men. Men are socialized to not feel comfortable talking about their dating lives unless it’s sex, etc. but they need to build up the courage to have other people (of both sexes) look at their profiles.
The second piece of advice is about creepiness. Men are afraid of being perceived as “creepy” – a lot of us women are very liberal, progressive feminists…and with the media talking about women being harassed and cat-called, it creates a fear in men where they are afraid of making any moves. Men end up getting “friend zoned” or don’t even try to ask a woman out at all. Please have an awareness of this and use it to your advantage. There are very few guys here that will directly ask a woman out. If you have the courage to do that, and genuine intentions around it, you won’t come off as creepy, and you will have a more fulfilling dating life.