A Holistic Matchmaker on Using Self-Reflection to Get Ready for Love

The Short Version: Handing your heart to a matchmaker means trusting they’ll treat it respectfully. Alexandra Freeman, a matchmaker, takes a holistic approach, so she handles her clients’ hearts gently but firmly. She encourages realistic expectations and self-reflection, which helps clients understand themselves better while also getting them ready for love.

It sometimes amazes me that a matchmaker’s guidance might well be the only thing keeping me from my forever person. I’d have to trust that the matchmaker grasped how weighty the role is. They’d be holding my heart, after all.

It’s fair to say that Alexandra Freeman grasps how serious her responsibility as a matchmaker is.

“I always knew I wanted to connect with people on a deeper level and do some sort of personal work,” Alexandra said. Once she saw how much joy matchmakers could bring into people’s lives, she knew she’d found her calling.

“I was like, ‘Oh, this is it. This is what I want to do.’” 

Alexandra shares her expertise with Matchmaker Alexandra and Introductions, Inc. Luxury Matchmaking.

Some matchmakers lean on tough love, and others give clients a “sink or swim” approach. Neither is a bad method, but neither is how Alexandra works.

So she brings a comprehensive, holistic approach to Matchmaker Alexandra. Driven by a deep-seated passion for helping people, Alexandra is well equipped to get our hearts ready for romance.

She begins by getting to know her clients completely… and then helps them know themselves completely, too.

Holistic Matchmaking Starts With Self-Reflection

Some matchmakers just want to check off each item on a client’s wishlist, while others try to give clients what they truly need. For that second goal, Alexandra considers everything, including a client’s background, career, non-romantic relationships, hobbies, and goals.

“I am a huge advocate for taking a holistic approach to matchmaking and dating,” Alexandra told us.

She aims for a well-rounded picture of each client so her match suggestions are on target. “Rather than approach dating or matchmaking from a very narrow point of view, we look at (the client’s) entire lifestyle,” she said. Her name for it is “a 360 degree perspective of understanding.”

Alexandra says self-worth is essential to a happy relationship.

Without knowing who you’re working with, meaning their history, fears, faults, and strengths, there’s no way to know who would suit them.

Naturally, keeping a healthy sense of self-worth is the client’s job. If you want a loving, fulfilling relationship, you have to believe you deserve love, right?

“That’s one thing I feel very strongly about,” Alexandra told us. “People need to take a more holistic approach to dating than just showing up and having dinner.” 

“My number one advice is self evaluation,” she said. She knows that’s hard, particularly if your self-confidence or self-worth is low. “It’s not a comfortable thing,” she acknowledged.

Then again, when has growth ever felt comfortable?

“The better you understand yourself, your needs, your wants, your features and flaws, the more success you’re going to have going forward,” she said. Better still, you’ll be able to “course correct when things go wrong,” Alexandra stressed.

Alexandra cares more about the quality of matches than the quantity.

Self-evaluation doesn’t require a therapist (though having one could definitely help). Simply writing out how you see yourself makes a solid first step. Alexandra recommends asking yourself hard questions, even when you don’t love the answers.

“How is my self-worth? How is my self-confidence? What is my social circle or social life like? Am I physically and mentally healthy?” 

In Alexandra’s view, these questions “tend to get neglected” across the matchmaking industry. Matchmakers can get so fixated on churning out a large quantity of matches that quality slips their minds entirely.

“Sit with yourself, ask yourself some very pointed questions, give yourself honest answers, and see if that honest conversation with yourself can help set you on the correct path,” she said. 

If these questions stump you, you may still have some work to do before you’re ready for a relationship.

Success Requires a Dose of Realism

Any matchmaking client can tell you that the secret to success is honesty with yourself about who you need versus who you want. Put another way, manage your expectations.

“I coach people to not be overly picky,” Alexandra said. In her view, landing a viable date through matchmaking comes down to keeping your expectations balanced.

That goes double for physical appearance. “There’s a nice, healthy balance between being overly invested in somebody’s looks and being realistic about your own personal preferences and needs,” she pointed out.

Love is within reach with Alexandra’s help… provided you speak up about what you need and keep your expectations realistic.

Alexandra has seen two extremes: clients who eagerly hand over a wish list of traits they want in a partner, and clients who feel such shame about hiring a matchmaker that they can hardly say what they want. Each type calls for its own approach.

Wish-list clients treat matchmaking like ordering fast food. “At the end of the day, we’re not ordering a pizza,” Alexandra said. “There’s a whole other person at the other end of this with their own thoughts, dreams, and hopes, and they have to be interested in you.”

Then you have the bashful client, who struggles to ask for help at all.

Alexandra told us there’s nothing shameful about turning to a matchmaker’s expertise.

“A lot of people are ashamed by the concept of needing a matchmaker,” Alexandra said. “They feel like they should be able to do it on their own.” She warned that one especially harmful mindset is this looping thought: “‘I should be able to find love. Everybody else can do it. Why do I need help?’”

Her advice? Keep in mind that matchmakers are like anyone else who puts their expertise to work helping others.

“It’s no more embarrassing than needing a lawyer to help you draft a contract or a personal trainer to teach you how to lift,” she pointed out. 

Shame too often blocks self-love, and self-reflection along with it, which makes love even harder to find. “Sometimes, we just have different skills and resources available to us than you might have on your own,” she said reassuringly.

Put simply? Be kind to yourself.

Be Open to Honest Feedback

The most attractive people value themselves enough to own up to needing love, and to needing help. “Just come into everything with realistic expectations and hope. Then we can work with you,” Alexandra suggested.

Matchmaking only works if you’re open to fresh ideas and suggestions that your matchmaker offers. When a first date doesn’t go as planned, you ought to find out why.

Success with Matchmaker Alexandra depends on your willingness to hear feedback.

Odds are good that you’ll hear from your matchmaker about what’s working for you, and, well, what isn’t.

“Feedback is so vital to the process that I actually put it in the contract,” Alexandra told us. “If you refuse to do post-date feedback, I will fire you as a client, because it’s so important to the matching process. The whole thing collapses without it.” 

That’s why your matchmaker needs a complete picture of who you are. If Alexandra sees early on that you won’t budge on your mindset, she might not take you on, and matchmaking itself may not be the right route for you.

Everyone has charming qualities, and everyone has some less charming ones. Wouldn’t you want to know yours so you can work on yourself and boost your odds of finding love?

You can trust that Alexandra vets her matches before they meet you.

“I can’t get a good gauge of who you’re going to like until I present you with someone and you tell me everything that was right and everything that was wrong. That is the most valuable feedback I can get,” she said. “Without that, I’m flying blind.” 

It all comes down to building understanding. Your matchmaker has to understand your needs, and that can’t happen unless you understand them yourself. You can’t understand them without putting yourself out there and welcoming feedback.

It’s a mental knot, but time and self-reflection can help you untangle it.

After all, finding love is a tall order if you can’t see why anyone would love you to begin with. In Alexandra’s words, “You’re going to increase your chances if you’re coming from a healthy perspective.”