Alessandra Conti was born with a natural affinity for romance. While other kids were playing tag, she was playing Cupid. “I have been a matchmaker since I was a little girl,” she smiles. “My sister and I would always set up our friends, but just for fun. We called ourselves sandbox matchmakers because we would be in the sandbox and say, ‘Jessica, you like Johnny.’ Our very first match and makeover, we were only in second grade. I’ll never forget, we did this makeover on one of our little friends, and then we took Polaroid photos of her and we then set her up with one of the boys in our school. We came from a small town and there wasn’t a lot to do. Through all of the milestones of Bar and Bat Mitzvahs, a group of girls would be on one side, a group of boys would be on the other side, and we would be the ones that were going in between.” The duo decided to turn a lifelong dream into reality. “My sister Christina was graduating with her Masters from Oxford, and I was graduating undergrad from American University in DC. We would always joke about how fun it would be to just move to Beverly Hills and start a matchmaking company. As we were graduating, that’s what we did. We moved to LA and all that we knew about LA was what we saw on TV. I had saved up $10,000 of babysitting money, which then became the seed funding for our company, Matchmakers In The City.” We all desire companionship and that yearning transcends every station in life. “I found that love is the great equalizer. It doesn’t matter if you are an A-list celebrity on the cover of every magazine or somebody who isn’t. It doesn’t matter. Everybody has issues with love.”
Before they knew it, a friend and new client was inviting them to swanky red carpet parties. The charisma and zeal of the two sisters became the foundation of an enterprise. “She told me to go up there with confidence and say, ‘I’m Alessandra Conti. I’m a celebrity matchmaker.’ So that’s what I did. And I mean, technically she was a celebrity and I had matched her, so it wasn’t a lie. That was my first experience on a red carpet. The events that we would go to were such fabulous young Hollywood events. We ended up meeting just so many incredible people and that’s how we grew. Almost 12 years later, we now have a team of seven matchmakers, myself and my sister included. We’ve matched so many amazing couples, and we have an office in Beverly Hills, and just a lot of success in matchmaking and then also in all the press and TV and fun things there too.”
Amidst growing mistrust of AI and the significantly shady shenanigans inherent in the usual dating app roulette, many are returning to entrusting their amorous fate to humans. Alessandra serves as a soft place to land for the deluge of disillusioned daters. “There has been this mass exodus of the dating apps. I think a lot of it has to do with the rise of artificial intelligence. People have major issues with the dating apps now because there are so many AI bots that are on these dating apps. It’s so difficult to stop them because everything is so real looking. Even the communication patterns appear highly intelligent. A lot of people are scared and they’ve been burned. They’re looking for a human being to verify that this other person that I’m about to meet is not only a real person – which is shocking that we have to be concerned about that – but also that they look like their photos because a lot of people don’t look a thing like their photos with all the Facetune. I am lovely looking, but I know my professional photos are different from how I appear in real life. This is the nature of the world that we’re living in right now. People are just craving not being one of a million – they want to be one in a million. And they are. They’re special. The paradox of choice is a real thing. People who are using dating apps in this fast food way, they’re not happy. It’s not yielding success when people are dating a million people versus focusing on really getting to know one person. It’s really damaging. People want to hire a human being to essentially be their human dating app. That’s a matchmaker. I think that that’s a big reason why there’s such a renaissance in the matchmaking industry right now.”
Fame and fortune aren’t a guarantee for happiness, as Hollywood insiders know. Constantly being under a microscope means losing public access to your authentic self. “I work with a lot of public figures or moguls or just really accomplished people,” explains Alessandra. “Those are my clients. And what I’ve found is the more successful that somebody becomes, the more isolated that they become, because they don’t have these natural communities that people that are not known can be a part of. If somebody is not known, they can be a part of their church community going to different events. Whereas with somebody that’s in the public eye as a celebrity, it’s really difficult for them to do that and not be the persona.” This phenomenon is often coupled with the double edged sword of modern conveniences. “With Amazon and Instacart and Uber Eats, these are all isolation devices. You don’t even have to go to the supermarket. You can get all of your food delivered. I have all my food delivered. You don’t have to go to CVS, you just order it on Instagram. It’s so great because we can then focus on work or whatever it is that we’re focusing on, but at the same time, it’s cutting off natural ways of integrating in the world. I find that the more successful somebody is, everything is sent to their house. They already have the sauna, the steam room…they already have it at their house. They have their makeup people, their hair people, all of that. They don’t have to go to the hair salon, they don’t have to go to Sephora. They don’t have to have those human interactions. It’s tough. It’s a blessing, but it’s also a curse.”
Even Alessandra herself is subject to scrutiny. “I’ve been on a couple TV shows and I have nasty Reddit threads about me. Yes, I’m on The Real Housewives of Beverly Hills as a matchmaker. I’m not one of the gals. I’m just a matchmaker for one of them. Even my Louboutins are ripped to shreds and people attack me on X. I experience an inch of what my clients do.” She understands the need to perform as a means of protection. Peeling back those layers slowly and carefully is a key component of her job. “What I’ve seen in working with celebrities is that a lot of them shield themselves as well. People that are in the public eye tend to do these kinds of coping mechanisms. They’re wearing a mask. What I do is fascinating and as a matchmaker, I’m blessed to see beyond the mask. I get to know anyone I’m working with, but especially for the people that really feel like they have to mask, I get to know them on a really deep level so that I can then find somebody that is compatible with their true self and not their public mask. Also, the beauty about matchmaking is that we conduct background checks, social media checks, and sex offender searches on all of these people so they can always know that and feel secure that anybody that I’m matchmaking them with has been fully vetted.”
The core philosophy of Matchmakers In The City revolves around pure intentions. “We focus on Introducing people who are genuinely looking for connections. They’re genuinely looking for their life partner. Our goal is to help people be the best versions of themselves so that when we’re introducing them to other really quality people, they feel really good when they’re dating and they see the value in the person in front of them. We’re very big on date coaching at Matchmakers In The City. We’re very big on tapping the experts that we have. Our very first expert hire was Mark Edgar Stephens, and he is a body language expert. He’s been Oprah’s guy and he’s been on every show as a body language expert. He works one-on-one with each of our clients on body language and courtship displays and attraction signals.” From there, it’s all about attitude. You have to believe in yourself and your own ability to connect first. In the haze of expectation, it can be difficult to remember that dating is supposed to actually be fun. “We have a stylist who works with the clients and does different date night wardrobe edits and date night shopping sessions that are so much fun. It just puts everybody in a better energy because the energy that you give is going to be the energy that you receive. If somebody goes into a date with negative energy, feeling self-conscious or anxious, people pick up on that. People are intuitive, so that’s why it’s so important. Those first moments are gold in a meeting or on a first date – having a positive mindset, giving yourself verbal affirmation: ‘I am beautiful.’ Looking at the person and thinking, ‘Wow, this person is so lovely.’ Just put that in your mind. Even if you don’t believe it, say, ‘Wow, this person’s so lovely. Oh my gosh, it’s so nice to meet you.’ You need to have these things streaming through your mind. Otherwise, the energy that you come in with is going to be repelling. And then everybody shuts down, masks go up, and then nobody connects because it’s talking from one mask to another.”
Alessandra has immersed herself in the joy of witnessing love journeys. She will carry the memory of a certain late client for the rest of her days. “I FaceTimed him the day before he passed away and he was in love. I had been working with him for a full year and I had just set him up with the most incredible woman for him. The last thing I said to him was, ‘Can you name your first child after me?’ I was kind of joking, but I wasn’t. He laughed and said, ‘I’ll think about it.’ He had a date with her and then he passed away the next day. I know this man was on cloud nine. After all this time working together, he felt like he really found her. He felt like we really found her. He was in love, and it was such a life-changing experience for me. Obviously, I miss him all the time, and it was such a sad story, but his life ended and he was in love. I introduced him to this woman. There’s really nothing better.”
In the doldrums of disheartening despair, we must dig deep to rekindle resilience. All forms of love are just around the corner. “We’ve worked with clients that have really lost a lot of hope. I think hope is something you have to have in life. If you don’t have hope, you have nothing. You also have to have faith, and faith and hope go together. One of the gifts that we have at our company is that we have a lot of hope because we see a lot of successful couples that have gotten together that didn’t have a lot of hope when they started with us – they were just feeling like they were at the end of their rope. I just had an interview with this lovely young man. If you looked at him on the street, you would think this man has no problems, especially in love. He has no issues whatsoever, but he was about to give up on love and on finding his person. I told him, ‘You cannot lose hope. You’re bringing so much to the table. Let’s light that fire back inside of you. If this is a dream that is in your heart, we need to ignite that fire and know that you will find her.” It helps to have an elite group guiding you every step of the way. “Our clients get pre-date coaching meetings and post-date coaching meetings, so they’re very nestled. The experience is very cushioned with matchmaker support. That’s why we have a team of seven matchmakers. I accept a very small number of clients because I emotionally can’t handle the ups and downs of so many clients. My price is just too high. My emotional sanity is just…it’s a high cost, but everything is possible for a small fee. No, I’m just kidding. But that’s why I accept only a small number of clients, whereas with Matchmakers In The City, we accept more clients because we’re able to service them with the team of matchmakers that we have who are incredible and lovely and affirming and give tough love when they need to, but are also really understanding.”
Love follows no timetable and romance can bloom for anyone. “I see the desire of the people that I work with that have this true, genuine longing to find their partner. I think that that is so beautiful. Even though it’s painful for a lot of people because they really want somebody, and either society is saying, ‘If you’ve hit this age and you haven’t found them, tough, it’s not going to happen for you.’ Or I think that a lot of times I see people that feel this immense pressure in their twenties to be with a partner that they know internally is not right for them. They end up getting married or they break up, but then they’re shamed because they did, and now they don’t have a person. It’s this whole thing. It’s so beautiful when somebody is able to develop themselves and wants a partner that compliments that life and adds to that life. The need is there. The want is there from men of all ages, from women of all ages. As long as that need is there, there’s so much hope for these people to find each other, because I think that we are meant to be in partnership. I think we’re meant to have the yin to our yang, the masculine to our feminine. We’re meant to find each other.” Alessandra relishes acting as the liaison for potential paramours. “I love the invisible string theory where people are connected by this invisible string. I think of myself as a little knitter. Sometimes I’m knitting and I’m taking the string saying, ‘Alright, it’s your time. Let me invisible string.’ I bring them together and our company and our matchmakers bring these people together. If a longing is placed in our hearts, it will come to pass. The challenge is staying optimistic, staying faithful, and knowing that everything is a lesson that is bringing us closer to the best versions of ourselves that will ultimately help us act out whatever our personal destiny is and our personal purpose is.”
The first step is letting go of fear and clearing away the past. “With hot air balloons, you have those weighted packs that are holding the balloon down. Those are the wrong people in your life. You have to cut those ties. A lot of times, it’s personal relationships. You gotta cut ’em so that you can then float and fly and be in that flow state. There’s a lot of hope though. People want love. That’s never going to change.” We can only reach new heights when we learn to trust ourselves.
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Celebrity Matchmaker Alessandra Conti Considers Herself a Crocheter of Love. Photo Credit: Courtesy of Matchmakers In The City.
