With dozens of dating apps on the market, the idea of a matchmaker can seem antiquated to some, but using a matchmaker goes beyond finding love. We sat down with Jaime Bernstein, matchmaker and client experience manager for Three Day Rule to discuss some of the finer points of engaging with a matchmaker. We discussed how to know you’re ready for a matchmaker, how a matchmaker can help you, what you can discover about yourself using a matchmaker, first date and early dating tips, and more. Watch this insightful conversation now!
Alyce Phinney (AP): Hi everybody! My name is Alyce Phinney and I’m a Wealth Advisor with Argent Bridge Advisors and the Director of Business Development and we are always trying to bring new content to our listeners, and people who watch our recordings and today we are so happy to be joined by Jamie Bernstein, who is a matchmaker for over 18 years in the DC area. She heads up the DC office for a company called Three Day Rule, and as a client experience manager, and today I’m just going to be sitting down with her and asking and she’ll be answering some questions today. So we will get started. Welcome, Jamie. How are you?
Jaime Bernstein (JB): Thank you! I’m doing well. I’m thrilled to be here.
AP: Great. Well, we have lots of questions or I have lots of questions that I know our listeners would want to know about matchmaking, and so just to get us started – tell me a little bit about what you are doing to help people find love.
JB: Yeah. So, I am helping people find love by not only meeting great compatible singles, but also really getting to know themselves and making sure they’re in the best, mental and physical space to get back out there to find and create meaningful connections.
AP: I love that. I know one of the things that we talked about where you said, you just mentioned it again about being in the right mental space – what does that mean? How does somebody prepare? How do they know that they’re ready to start dating or get back out on the dating scene?
JB: Yeah, so the number one thing I find that really helps singles find success in dating is, first, making sure you’re happy with what you have going on in your life. And that can be different things for different people. But, when you feel really good and really confident about yourself, what you have going on, and who you are, that’s when you’re in the best place to actually find and create the foundation for a healthy happy relationship, and really bring your best self to the dating arena. So, the number one thing is reconnecting and finding out who you are and feeling good about that.
AP: What should they be looking for to know that that’s where they’re at?
JB: Yeah, so I would say the first thing to think about is, do you feel happy?
I know that’s a generic term, but do you feel pretty good about who you are, what you have going on? Are you seeking a relationship to find happiness? That’s a big red flag. When someone comes to me and they say, I have a great job I made plenty of money and I have nice friends but I’m not happy, and I want to partner to make me happy. I know they’re not ready. So, if you’re using language like that that you’re seeking the relationship or the dating experience to be happy, you’re not ready. You need to be happy first and then wanting to be in a relationship to enhance life but feeling as an individual that you’re happy with what you have going on.
AP: Absolutely. I love that. Tell me or walk me through a little bit about your screening process and who your clients are at Three Day Rule.
JB: Yeah, so we have a pretty wide variety of clients a Three Day Rule. Everybody is financially well-off and stable in their career, in regard to that aspect, but we deal with people in all phases – never been married, divorced, widowed, out of the dating scene for decades. So, we provide not only quality matches, but also the coaching needed to really make sure that you’re in the best place.
And the screening process involves having a one-on-one meeting initially with me, and then potentially another matchmaker who somebody may be working with depending on their needs, but really diving in and getting to know who that person is. And what they’re seeking both on and off paper qualities – age range, religion, family planning, lifestyle, but then also humor, “what you like to do for fun”, “what kind of energy you bring”, “what makes you unique”. Finding that right balance of on- and off-paper qualities, who you are and also the on-paper things that matter.
AP: Tell me when you talked about the coaching and things that go into getting somebody ready to go out on a date – what exactly are you doing? How much hand holding are you doing?
JB: It’s really customized to best suit the client’s needs. Some clients are pretty ready to go and just need a few tips and tricks about how to manage an awkward pause. If they are a single parent – how soon and how much we’re talking about my kids. Some of these tidbits that can just be tightened up to help somebody really present their best but also authentic selves in early dating.
Other clients are fresh out of a divorce and like, “I don’t even know who I am”. The first step there, day one, I’ll say “what do you like to do?” “Who are you?” Often and especially women who have been married for a long time may have lost a bit of their identity. I’ll start with “what did you like to do when you’re a kid?” People will think and it could be from baking to painting to gardening, whatever it may be. And then they almost reconnect with whatever that activity or thing that used to bring them joy is to start the journey of rediscovering their individuality outside of the role of a wife and a mother, for example.
AP: I love that. Give me an idea of what makes a perfect first date. What would it look like?
JB: So a great first date – I think is the generic drinks which I know is not that exciting (if both people do drink alcohol). Otherwise, coffee or ice cream with the appropriate as well.
But you really don’t want to have a lot of pressure or concern about an activity date or a really fancy restaurant – things that would come down the road if you guys did connect. So something like grabbing a drink.
Being able to hear each other, so you want to plan on the environment. How are the acoustics? How crowded will it be? Making sure you’re comfortable with the actual place, and then limiting that first encounter to two hours or less.
Why that tends to really yield success is because there’s something that happens on a first date, even if it’s going really well, when people are out for six hours or eight hours where it’s really fun but it’s almost just too much emotional energy too quickly. Also, sometimes people make bad decisions too many drinks over several hours and end up doing things or saying things that they may regret.
Keeping those one or two hours really keeps the date fluid and exciting. And the best thing to do at the end of the date after two hours and you both had a great time – get that second date locked in right there so you both have something to look forward to. But really managing the time and the environment can really help facilitate the best possible connection.
AP: I think a lot of people would be really surprised to hear you give that answer because lots of times you go out on a date, and you have this connection you just want to keep going and going. The chemistry pair and it’s hard to break away from that chemistry. So I think that was really surprising for me to hear and probably our listeners as well. I just think that’s something that we’re not used to because we want to have more and more.
JB: That’s right. And I challenge anybody out there dating to give it a try, and I almost guarantee results will be better. Because again it’s not though as though you’re signaling that you’re not interested or you don’t like somebody, it’s really making sure that the time spent together is quality, and that you can set up another date because dating is one of the few things in life that forces us to be in the moment in real time. We have to be there, we have to be present, and experience the connection. “How are we feeling?” “Am I having fun?” “Do I find this person attractive?” In early dating, those should be the things that you’re concerned about. How do I feel? I feel good, I feel excited. And then, wanting to spend more time because dating requires us to spend time together and get to know each other over a period of time versus knowing you after one day. Is this person going to be my person for the long haul or not?
AP: Absolutely. So we talked a little bit about what makes a great first date, but give me some of the ideas of what the biggest dating disasters you’ve heard is.
JB: Boy, do I have a lot of those. I would say one of the biggest dating disasters I see the most common is what I call “airing your dirty laundry”. So sometimes I will have a client, I’m just going to tell my date about my ex and my health condition that’s negative and this and that because I want to take it or leave it. They need to know who I am and that’s it. And I understand where that mentality is coming from. But the truth is, we’re all just people, and so we need to first facilitate a connection to see there’s enough there to even propel the relationship forward before really sharing the deep aspects of who we are both positive and negative. So it’s never that you’re hiding, or that you’re lying or being deceitful, it’s more about knowing when and how to share the different parts of who we are, and when it’s appropriate. That’s the key.
The truth is, everybody feels better with a smile and feeling good. So very early dating, I’m talking dates one and two you really want to create an environment that’s positive, that’s upbeat, that’s authentic, that feels good. So highlighting the positive qualities that you have.
AP: Let’s just say you’ve got some dirty laundry. And you want to test the person, test relationship – you don’t want to bring it in right away, but at what point do you start introducing those things?
JB: Yeah, it’s a great question. There’s a little flexibility here but I would say, if there is mutual interest usually, you’ll get to at least date three. The way the dating environment is now a lot of people go on first dates, less people go on second dates, even less get to a third date with somebody. If you both have agreed to a third date, typically there’s a fair amount of mutual interest. At that point, you can start to open up a little bit more, maybe share a little bit more dirty laundry or baggage. And the key is – whatever you’re sharing, it’s about sharing it in a competent manner, and also sharing how you’re dealing with it. Whether it be something from your divorce is or with yourself, whatever it is, it’s about articulating it and saying this is what I’m doing, moving forward, to remedy or deal with this situation.
It’s presenting whatever that issue is, and then how you’re dealing with it. In as positive of a way as possible. You don’t want to just go even hang and you want to be able to move forward with that conversation.
AP: Let the other person know that you’re taking care of yourself.
JB: Exactly, exactly. You want to think about it. There is nothing wrong with preparing or doing homework before dating. People think you should just go on a date carefree and not think about it and just see what happens. But there’s nothing wrong with preparing especially if you’re going to broach a difficult topic, or you share something very vulnerable about yourself, practice at home. You don’t need to tell the date that you practiced. Right? But if you go with that added confidence it’s only going to help make that a smoother transition in conversation.
AP: That’s a great suggestion, I love that. So tell me a little bit about Three Day Rule and what sets your company apart from some of the other matchmaking companies out there.
JB: Yeah, Three Day Rule Matchmaking. We’re a national company so we’re in all the big cities in the East and West coast. We’ve been around since 2013, and we are such a great resource for singles, because it’s a company that really is founded on not only helping singles and finding great fits but also the coaching. We’re really about a holistic approach. The company is so ethically based. We have an astounding team of matchmakers, where everybody cares about the clients and really, really customize our experience to best suit the needs of every individual client that we have. And the internal environment with Three Day Rule is so positive. Every week we have a call where the first thing we do is we share our successes, and we really collaborate and support each other and that translates into the type of service that we provide for our clients.
AP: And what about – like where do the clients actually come from? Are they paid clients match with other paid clients? Or how does that work?
JB: Yeah, so we have, we really do have options for everybody.
We have clients who pay us and that is our premium membership and that involves the coaching at a very high touch experience. We also have a database that singles can sign up for free. And if we do have a paying client who might be an adequate fit we reach out and vet them and screen them through our protocol.
So if you’re really looking for very active approach that’s definitely the paid premium membership. But we do have a database that has no cost that people can join as well.
AP: And then tell me a little bit how you personally got drawn into matchmaking. I mean, it’s just fascinating like if you have a history of it.
JB: Yeah, so I the best way I can really phrase it is I got into matchmaking because matchmaking got into me. When I was in middle school and high school I worked at a pizza place and I was a teenager of setting up my boss who was in her 40s with customers and it’s just always been something that’s been in my blood that I love to do, and I’ve really been able to hone my skills to be great at it and I have so much passionate around it so I don’t know one day woke up and I was like, I know about love and I’m going to help people.
AP: I think that is fantastic. So just to close it out just thinking about COVID and how that has maybe changed all the ways people are dating and I know that people are spending, well during COVID stay at home, people are spending more and more time having Zoom meetings, having phone calls, things like that. What do you think is going to change? Like what is it, what do you think the landscape is going to look like for dating six months or a year from now? Like is that going to stick?
JB: So right now, the current dating landscape has been coined the golden era of dating, because there has never been a time in our living history that the world has literally push pause on life.
And so many people have had time to reflect because they’ve had nowhere to go and nobody to hang out with. And so the value of a meaningful connection has been highlighted.
So what that translates into now, as well as reintegrating into society and getting back out there again, is that so many people are interested in a relationship versus the hook up culture of course that still exists in the casual dating but as much less than ever before. So now is absolutely the time to seize that. Get out there find meaningful connections, people are slowing down, having more conversations, getting to know people, and really enjoying the process of what that involves.
AP: I really look at this whole process just putting an investment into yourself, just like you would in anything else in life, spend the time do the research spend the money. And really invest in yourself because the ultimate goal is to find that partner.
JB: Absolutely. And when you’re in the place that’s ready, finding that meaningful healthy happy relationship just enhances your life, it makes like deeper. It’s more colorful, it’s more filled with love, and when you’re a happier individual you’re a better parent, a better employee, a better self, and so it’s really a win, win you get to the place where you can find that meaningful connection.
AP: Well this has been so fun sitting down with you, having a great little conversation, and just let us know how can we connect with you.
JB: Yeah, so you can find me on ThreeDayRule.com and you can email me at jaime@threedayrule.com . Jaime at three day rule. You can also follow me on Instagram. It’s @matchedbyJamie, but I’d love to hear from all of you.
