Sasha Silberg is 24 years old and has her own matchmaking agency: OKSasha. Naturally Sasha is up-to-date with all of the modern lingo when it comes to speaking to Millennials. After all, she is one of them. Added to that, Silberg is a far cry from the old idea of a matchmaker: a frumpy, middle-aged aunt who sorts people into couples, sends them on dates and hopes they get on. No, Sasha’s got a different approach!

A Modern Wingwoman

That’s exactly what Sasha Silberg considers herself: an older friend or “wingwoman” who can help others pick out the right date. The word “dating coach” has also been suggested, which definitely puts a different spin on things! As well as offering matchmaking services, she’s happy to dole out advice. And of course, Ms. Silberg is not the only one. There seems to be growing pool of Millennial matchmakers who are looking to create the perfect dating service to fit their generation. Among the many superficial dating apps out there today, it’s nice to have a human touch.

Matchmaking and Dating Apps: A Compliment, Not a Replacement

These Millennial matchmakers are not looking to put dating apps and sites out of service. Rather, they are hoping to act as complimentary services that can help both men and women choose the right date. Silberg says: "People sign up to date with me because I make dating fun, and I help people be themselves more," Silberberg told Vice. "If you're not acting from your most authentic self during the dating process, you're going to have a really hard time with what you're actually looking for."

Not every wingwoman and dating coach work alongside online dating services. Some, like Sofi Papamarko, work exclusively offline or in the “real world”. They often use acquaintances of theirs, or match their clients with one another using the database that they have. According to Christina Weber, who runs a matchmaking service called Underground Unattached, this generation need guidance.

She elaborates that we’re simply not taught the “how” of relationships with others. As a result, Generation Y is a little confused when it comes to settling into relationships whilst putting focus on their careers at the same time.