The baby-faced cupid, who aims to bring dating back to old school, person-to-person interactions, told Vice that people going on a date should never meet for coffee, because "that's what every m**********er does" and it's "boring".
Ms Silderberg, who is part of the growing matchmaking industry for millennials, by millennials, focuses on hooking up clients under her very watchful eye.
"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."
So what secret potion do these 'experts in love' hold that the rest of us stuck in singledom seem to lack?
While the growing number of matchmaking millennials (who often refer to themselves as wingwomen) are on the rise, they like to be considered as well-informed friends, rather than dating professionals.
"Having a matchmaker is having a really well connected friend," Samantha said.
"We work on defining what they are looking for, their past relationship patterns, how dating went wrong in the past and how to fix it in the future. Some get a makeover, some get styling and some even see a trainer.
"Some clients I go with [on dates], while others it happens it quite organically.
"But before their first date, I advise on what to do, what to ask, what to wear. I really mentor them in keeping the mindset right, because nerves can often get in the way."
But despite Tinder and other dating apps providing a free platform for single souls to find a date or a hook-up, 'old-fashioned' matchmaking seems to have simultaneously grown in popularity.
Samantha believes that while the surge in social media as a dating platform works for some people, there's a real gap in getting your profile right and attracting a suitable match.
"With apps like Tinder, it's all about a checklist, and that's a real issue," Samantha said.
"The incredible thing about these apps is that they are free and open up so many doors for people.
"I have found an area to empower and educate using the apps, because 95% people aren't succeeding when they use them."
While Samantha charges her clients $3,500 for a 6 month intensive course, her successful results speak for themselves.
"It is a significant investment for some, but we work together on a profile that is successful," she said.
"I have matched thousands and thousands of couples, and most have stayed together or got married."
Samantha said that while dating apps work for some people, they also allow for hundreds of missed opportunities.
"With Tinder, they keep swiping and missing so many opportunities," she said.
"We drill down on what they want, and be really specific - from the bio to the pictures they choose.
"We get to know our clients, find out what makes them tick. That's how we match them with someone who is complementary to them.
"While opposites attract in the short term, we look at our clients long-term goals. The people we match need to want the same things, so they are on the same page in 10-15 years time. We like to focus on all the things that really matter once the honeymoon period is over."
Since when do 20-somethings actually know what they really want, especially when a platform like Tinder provides an endless list of first-date options?
Christina Weber, who is a matchmaker and founder of Underground Unattached, said the answer is quite simple - "millennials want guidance".
"I think that we're not taught how to have relationships with people," she said.
[Millennials] are a little bit confused with how they navigate the relationship while they focus on building their careers. They want close relationships but don't know how to do it."
Samantha admits that anyone, at any age, can succeed or fail when it comes to finding love. Some people go into the experience of matchmaking with an open mind, while others are insistent on finding roadblocks to obstruct the journey.
"I've matched people with the first and second person I introduce them to," she said.
"Others might take longer, it really comes down to if you want it to happen, then it will happen.
"You can find roadblocks if you want to, but if you trust the process It will happen for you."
People used to meet their partners through family and friends, but now internet meeting is surpassing every other form.
For many singles in their 20s or early 30s, the idea of hiring a matchmaker may seem old-fashioned and a waste of time, money and effort. But those behind the service insist it cuts through the timewasters, and the formidable abundance of options found online.
"Millennials are educated and they've spent all this time perfecting how to think with their brains, but dating is tapping into your feelings and emotions," Laurie Davis of eFlirt told Vice.
"There's so much choice out there, and often they get overwhelmed by the option and nothing gets done," Samantha added
"People take on these apps, and they play but they never meet because they are nervous meeting face to face. They are on this treadmill of singledom and can't get off.
"The fun of it fades, and becomes quite empty. That's when they look for someone genuine, and we help with that."
