Relationship Advice From Expert Matchmaking Duo

Dyana Goldman
6 min readDec 10, 2019

Destin Pfaff and Rachel Federoff are internationally renowned relationship experts and matchmakers who own Love and Matchmaking, a one-stop-shop for love. With hundreds of successful matches under their belts, and a thriving relationship of their own (the couple has been married for eight years), who better to ask about all things relationships than these two?

From my single friends (aka self-partnered) to my married ones, and everyone in between (and by everyone I mean, me, who is moving in with my boyfriend this weekend), we’ve all got questions.

In a world of Tinder, Bumble, endless text messages and ghosting — basic and Caspering — things have gotten pretty complicated. Destin and Rachel agree and so do many of the clients who come to them seeking love. The matchmakers preach methods that many would scoff at, but their old-fashioned ways may just land you a lasting relationship. And really, aren’t you tired of the bullshit?

The matchmaking duo has quite a handful of rules they require their clients to adhere to and advise anyone dating to follow. Rachel says people who want to go out on coffee dates, “make us want to gouge our eyes out!” They say a proper date is a dinner, at night, preferably on a weekend. The male (in a heterosexual relationship) should initiate the date as well as the required kiss at the end. The Little Mermaid had it right: “go on and kiss the girl!” They also don’t stand for the “nonsense of texting.” On that first date, stay on neutral topics. Their holy-grail rule: don’t talk about your ex. Add to that religion, politics, kids…you want to be, as Monica from Friends says, breezy!

If you’re someone who goes on multiple online dates on a weekly basis, a dinner may seem too intense for you. Similarly, if you’re the one paying for these dates, budgetary confinements could also make this seem unreasonable. However, this is part of the problem. When Rachel and Destin are setting up dates, they are looking for the one, not “all of the ones.”

If you’re not working with a matchmaker — and the good ones, like these guys, ain’t cheap — you can still utilize their advice. Don’t date just anyone who asks but rather focus on finding someone you are genuinely interested in, and give them your full attention. I asked the matchmakers in this online-dominated society, should someone be dating multiple people at once to increase their odds at finding love?

“Life is complicated and life is busy. The way we look at it, your love life should not be complicated, and not busy. Dating one person at a time is enough. If you like and enjoy them, go on a second date, and if you like and enjoy them again, go on a third date. If there are red flags or you feel like you’re settling, stop talking and stop dating them,” Destin advises.

Furthermore, they advise against dating multiple people because of all the complications that brings. Before I met my boyfriend, I was dating several people at once, and certainly had a “grass is greener” attitude where I’d want to Frankenstein the personality of one date onto the body of another. I’d start to compare, and I would feel overwhelmed and stressed out. I’m guilty of ghosting and while it doesn’t feel great (on either end), isn’t it okay to sometimes take the easy way out? Destin and Rachel don’t think so!

They believe you should absolutely tell someone after a first date if you’re not interested. I think from the perspective of someone who is constantly going on multiple dates per week, this may seem unnecessary. When it is a setup or someone who is not completely random, however, the dates hold more weight. In that instance, I can agree that letting the person know there will be no future is the right thing to do. Destin and Rachel suggest, if possible, giving a referral. If you liked the person but felt no chemistry, is there anyone else you know that may be a better match for them? That’s one way to pay it forward!

If you are active at online dating, Destin and Rachel have some thoughts on how to have the most success. They advise people to have the right type of profile: honest and without too many filters or revealing photos. To avoid overwhelm, choose one or two, at most, platforms to be on. Things should flow pretty quickly, in their opinion. After a few messages exchanged with someone you’re interested in, there should be a 10-minute phone call, followed by a proper date. That guy who texts like he’s looking for a penpal? Forget him.

The matchmakers are all for putting a timeline on relationships. Once you find someone you like, they say you should know by the end of the second date if the chemistry is there or not. First dates are difficult. People are nervous, it can be awkward, and not everyone feels that instant sexual connection. The matchmakers think everyone deserves a second chance unless your date shows major promise to be the subject of the next season of Mindhunter.

Since things seem to progress pretty quickly under their methods, by three to five dates, they say it’s time to commit to a monogamous relationship. Those earlier off-limit topics are relevant and important. If your non-negotiables (for example, must want kids) are the same, and both of you are able to compromise on what needs to be compromised on, we’ve got ourselves a serious relationship!

While the matchmakers promote a more traditional route, they’re not entirely of your grandparent’s mindset. Sex is a-okay once you are heading toward or in a committed monogamous relationship. Sex on the first date, however, is a terrible idea. Having sex too quickly when you are dating multiple people, or before you even have that first date, leads to questionable relationships, complications, and a whole lot of headaches! You know the old third-date rule? For the most part, follow it. If, that is, sex is important to you and you’re feeling it.

The matchmakers are also big advocates of moving in together before an engagement. This is the stage where all of the truths come out: you get to see every skeleton and not-so-cute habit your S.O. has. If you still want to marry this person after you’ve seen them eat Pad Thai over the kitchen sink with their hands, then you know it’s meant to be. After about six months of living together, they better put a ring on it, or Destin and Rachel say it’s time to move on! They’re not fans of wasted time and really, who is?

First comes love, then comes marriage, then comes the baby in the baby carriage. Then comes sleepless nights, hectic schedules, and unless you work at it, a stagnant marriage. You’ve probably heard it before, but amongst all the chaos of day-to-day life, the matchmakers say scheduling a weekly date night is a must.

It doesn’t have to be a big night out on the town, and it could even take place at home. Destin and Rachel’s son will make fun of their date nights, as he willingly goes to hang in his room, allowing his parents their needed privacy. They’ll roll out a picnic blanket and enjoy some wine and cheese, maybe even light some candles. Sure, it’s a bit corny, but after speaking with them, I think it’s time to make corny cool. #cornyiscool2020

To keep the romance alive, let your childlike nature show, and be silly and playful with your spouse. They say kissing or even wrestling, helps to maintain that youthful attitude of when you were first in love. Pair this with open and honest communication, and you’ve got the equation to a lasting relationship.

Whether you are single or attached, you should be completely at peace with yourself if you are going to make a relationship work. Loving yourself, respecting yourself and knowing your worth will make you confident. “This is the sexiest thing in the world,” Rachel says. Destin adds the perfect complimenting sentiment, “You don’t need anybody but you would like somebody.” No matter what you do to find love, don’t get discouraged, don’t get frustrated, and never settle.