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Jaime Bernstein is a senior matchmaker with Three Day Rule, a website devoted to helping you make your best decisions when it comes to love as opposed to me whose one requirement for a mate is based entirely on a scene from the movie Singles.

I hopped on a call with Jaime to find out exactly how all of this works as clearly it feels outdated and possibly insane but is it really crazier than say…meeting someone simply because they’re 6′ 2″???

Brightest Young Things: We’re talking about dating at 10:30 in the morning, which is not the most romantic hour of the day.

Jaime Bernstein: I talk dating all day every day so that works for me.

BYT: There is no romantic hour, is there?

JB: Oh, it’s all romantic.

BYT: That’s probably the best way to look at it and part of the reason why I’m usually single. There is no such thing Jaime. So Three Day Rule…before I went to the site I was afraid this was a reference to when you should sleep with someone and I said to myself “Hey if you want to sleep with someone on the first date you should absolutely sleep with someone on the first date.” This is why I’m “great” at dating.

JB: This actually comes from the idea that a man should wait three days before calling a woman he’s interested in so it’s not about sleeping with someone.

BYT: Oh. I’m romantic. I think my editor forwarded me this interview opportunity because I’m essentially the only single person in the office and I’m 37 which is 89 in women years. I also think part of it was “You should talk to this person because you’re single.” and “You’re single.” This service sounds very old fashioned.

JB: Three Day Rule brings in that element of person-to-person connection. It is old school matchmaking but we’re very modern, very fresh. We utilize technology of course and puts a modern spin on matchmaking. It sounds like you’re a dater yourself in a time when technology is very much present in the dating world. It causes a lot of stress. It can be very overwhelming and chaotic with all the options, apps.

BYT: I’d go as far as to say technology can be a bit of a relationship ruiner.

JB: I tend to agree with that.

BYT: I was just telling someone the other day that I don’t even like to be Facebook friends with the people I’m dating because so many things can be taken out of context, and it’s mostly by me because I’m kind of a wild card. I’m very firm about not being social media pals with folks I’m seeing. People seem to have gotten along without Facebook since the dawn of time so I think we’re going to be okay.

JB: I don’t think there’s a reason you need to be FB friends super early. It does create judgment.

BYT: What is the Three Day Rule process?

JB: Generally people sign up on our website and are assigned a matchmaker, either myself or a colleague. We then set up an in-person meeting where I get to know more about them, what they’re looking for, and what they’re doing.

BYT: So you get your matchmaker and you meet. They get to look directly into your eyes to see if you have a soul. Step 1.

JB: We have paid client options where we have a contract or we have a free option where someone can be active in what we call our Free Pool which allows them the potential to be matched with a paying client.

BYT: You’re gonna want someone who’s paying or you’re going to get the dregs of society. If you’re paying maybe you care a little bit more. Now I’m just going to shame everybody.

JB: Most of the paying individuals I work with I end up matching them with people who aren’t paying because I’m looking for really deep intangible qualities as well as lifetime goals, foundational type things…so it’s both. D.C. is filled with all kinds of people.

BYT: So if we were sitting down together, you and me, in a safe public place…what is it you ask me? I think the first thing everyone should get out of the way is do you want to get married someday or do you want children someday? A friend of mine said you should wait for the third date but why even waste those other dates?

JB: So if someone is a client of mine I do need to know their goals. Are they looking for a long-term relationship? Are you looking to get married someday, have a family? Age, religion, all that good stuff.

BYT: The age thing hurts my heart a little bit because as you know I’ve already aged out of dating.

JB: No you haven’t.

BYT: Oh I have about half an egg left. It’s okay.

JB:  I deal with women older than you. There is no expiration for love. So once you kind of get through the basics then we’re getting more into the nuances of who someone is. What do you do for fun? What’s your sense of humor like? Are you  more active? Are you more of a couch potato? What are some of your long-term plans in the sense of where do you see yourself in 5 years?

BYT: Is there a more scientific way of figuring these things out? Some people may view themselves as A, B, C when they’re really X, Y, Z. A lot of people want to think they’re extroverted but maybe they’re not.

JB: There really isn’t a scientific way to figure these things out. We get into an hour long conversation and people really do open up and become more genuine and we also discuss what it is they’re seeking in a partner and why. Sometimes people are seeking things that aren’t really realistic so part of my job is helping people figure out what their goals actually are. It’s important to be open, honest and realistic. Everyone has flaws so no one is going to find a perfect match. When people start talking about a perfect match I always kind of say “That doesn’t exist. No one is perfect.” There is always going to be compromise. There is always going to be give and take.

BYT: What happens after this meeting?

JB: I utilize my free pool of singles in the D.C. area which at this point is a little over 13,000 people, using technology to sort through the sheer numbers to break things down. Maybe I’m looking for someone who is Christian and has these particular hobbies, is educated…I’m able to cut through lots of people to narrow that search down. When I get that down to a reasonable number I meet those people in person to see if those tangible things are there. Once I find someone I really like for my client I’ll send them a brief bio and a picture of my client to see if they’re interested in meeting him or her. If they agree I send the matches’ information to my client and if there is mutual interest I pass on the women’s phone number to the man. We find women, whether they’re paying or not, they like to be pursued. It’s a little old school but people want that and they expect that. Of course it can happen any way.

BYT: Is there some kind of database you’re using to sort out folks? You plug things in and people come out.

JB: In a way…we limit several hundred potential options to something more manageable. Generally I’m reaching out to between 2 and 15 or up to 20 individuals.

BYT: What is the success rate? I don’t know what success means. I suppose it means a relationship. It doesn’t necessarily have to be MARRIAGE. Do they let you know?

JB: Success can come to fruition a few ways. If someone wants something long-term and they achieve that, great. Another thing that happens is, due to the feedback and the coaching that happens, it can be life-changing. Some people aren’t aware of how they’re presenting themselves on dates. This can really help open people’s minds and increase their confidence.

BYT: Now Jaime, I do not want to question your expertise, but what makes you the expert on dating and matchmaking?

JB: I started being known in my circle of friends as a matchmaker from about middle school. I was always setting up my friends and throughout my whole life have been interested in connecting people in terms of dating and love. For me it’s my job and it’s also my personal interest and passion. In terms of education I have not completed any sort of matchmaking certification though there are some different matchmaking institutions out there but to be honest they don’t really hold a lot of credibility in the field because when you’re good at matchmaking you’re good at reading people and listening to people and picking out the innate qualities that are compatible. It’s something that’s really hard to teach. For me my educational background is I have a Masters Degree in training and development which is how you deal with people, how you figure out who is compatible.

BYT: What are we doing wrong on our dates? I’ll be honest with you Jaime. I don’t date a lot. I have a lot of reasons that I happily go into on my own personal Facebook page. I have a dog who once urinated on a man’s pants when he was at my home. She knew. Would you say that being too open is bad? I like to get the worst of myself out up top so there are no surprises. I like to fire off the questionable things I’ve ever done so if you’re still there we can hang out. That’s probably bad.

JB: In love and dating there are general rules that tend to work and things that won’t but there are always exceptions. Not everything works for everybody. The reality is…there are a few general mistakes people make.

  1. In today’s dating landscape where we live in such a fast-paced environment, people give up too easily. It takes a little time to get to know somebody. If you met online or like this there is always a little bit of awkwardness or a little bit of nervousness. If it’s decent, you found them reasonably attractive you enjoyed yourself, go on a second date.
  2. Putting all of your dirty laundry out there? Don’t. We all have baggage. We’re people. We have flaws. The reality is you have to see if you connect on the lighter things. Do you like to travel? What do you do for fun? You want to see if there’s a connection. If you immediately know something unappealing about someone you’re going to ask yourself if it’s worth seeing that person again. If you connected with somebody after one or two dates and you’re excited to see them again, you may be open to dealing with that dirty laundry. The bad stuff is part of you but that doesn’t define you. Don’t unload the heavy stuff right away. Relationships and connections do take time to develop and strengthen.

BYT: Again, not a science HOWEVER, how many dates should you give someone.

JB: If you have a reasonable connection and you’re having a pretty good time, give it three dates. If you don’t want to hold this person’s hand or you have nothing else to talk about, then you put in adequate effort.

BYT: It’s so obvious too. Anyone reading this would wonder why anyone would do ANY of the things I’m doing. I don’t know, I’m very terrible at dating.

JB: Telling yourself you’re really terrible at dating makes that your reality a little bit too.

BYT: Oh no Jaime now we’re having a therapy session! How did this happen???

JB: Surprise! It’s true. The conversations and stories we tell ourselves are setting us up to fail if they’re negative. That mentality can change the outcome.

BYT: What one thing do you try to get out of people?

JB: The number one thing I like to talk about that I find very helpful is their humor.

BYT: I’m good there! Men do NOT like that. Don’t let them fool you.

JB: I can tell you’re kind of sarcastic..

BYT: Were you looking for negative AND dark? Those words.

JB: You have that kind of British style.

BYT: Yes! I’m quoting you on that.

JB: Humor is an important connector for people. For example if you were with a guy who didn’t get it or thought you were too dark for him…even if he thought you were super attractive and smart, eventually you guys would feel disconnected because you can’t really joke around and be yourself. For me when people say they want someone with a sense of humor I need more information than that. What does your humor look like? Some people are offended by sarcasm or they don’t get it. Other people like a more classic style like going to a movie and laughing but they don’t really joke around outside of that. There are a lot of variables. For me that’s one of the things that’s kind of not your typical basic stuff I like to get into.

BYT: We’re accidentally doing a matchmaking session right now. We’ve shifted seamlessly out of an interview and straight into my free matchmaking session and I hope the Internet enjoys it!

JB: I was gonna tell you is you should get a free account.

BYT: Maybe, if we met in person I would drop all my terrible nonsense off at your doorstep so you can see all the things that are usually deal breakers for people. How long does this process take? When is a client no longer a client.

JB: We have 3, 6 or a VIP contract which is a year. People can renew. If someone is active in our free pool they kind of stay there until they let us know they are no longer interested in being there.

BYT: Final question! In your expert opinion…am I gonna die alone?

JB: No…not if you don’t want to.