How A Great Matchmaker Sees Compatibility, Insights From Matching Thousands of Couples (w/Dara Rahill)

Today, I am joined by Dara Rahill, a former top-ranked premium matchmaker at the country's largest matchmaking platform, and now the founder of Dara Rae Matchmaking, to reveal what actually predicts a healthy long-term relationship when you look beyond photos, height filters, and perfect-on-paper stats. 

We dig into the behind-the-scenes reality of modern dating:  “checklists”, dating profiles, and how dating app culture amplifies snap judgments. 

Dara explains how real compatibility is assessed, plus the intuitive “art” a matchmaker develops after interviewing thousands of singles. We also unpack why even highly sought-after people sometimes choose high-end matchmaking services.

One of the most eye-opening parts is who can be hardest to match and why. We also challenge the myth of instant chemistry, exploring how attraction can grow through repeated exposure.

If you’re tired of guessing, lower-stakes clarity starts here. Great episode for both men and women.

🎀 Dara Rae Matchmaking

🫶 Dara Rae Instagram

Transcript

Welcome And Why We Want Love

Host Tea 0:04

Hey you welcome to The Dating chit, a space designed to help you move beyond assumptions and guesswork, so you can date a love with clarity and confidence. I'm your host , Tea. Today's conversation is one I've been really looking forward to. I'm joined by Dara Rahll, who is once a top-ranked matchmaker at one of the largest premium matchmaking services in the U.S. And is now the founder of Dara Rae matchmaking, a highly personalized service behind many love stories in the Philadelphia area. And when I say she has seen all she is truly seen at all from incredible, almost cinematic love stories to patterns that highly sabotage, even when the most perfect on paper matches. And here's something that really caught my attention. Do you know what type of client is usually the hardest to find a match for? We get into that, and it might not be who you expect. In this episode, we're discussing matchmaking, compatibility, and getting a behind-the-scenes look at what actually works and what doesn't when it comes to finding a lasting relationship. We also take an honest look at what modern dating is doing to our expectations and how to come back to what really matters. So if you've ever wondered what truly makes two people compatible, or you're curious about premium matchmaking and whether it's something worth considering, this episode is for you. Let's get into it. Hey Dara. Hi, Tea. Good to see you. I'm so excited to have you on this podcast today.

Speaker 1:44

Same here. I enjoyed our conversation the other week when we first met.

Host Tea 1:48

Definitely, yeah. I'm just gonna dive in directly to the question that I prepared for you. And I'm pretty sure our audience is also very excited to hear what do you have to say about as a matchmaker who have so much experiences. Before you have started your own firm locally at Philadelphia, you were the number one matchmaker and recruiter on one of the largest premium platforms in the US. So my question here is: what is the most important truth about love seeking you've learned through your work?

Speaker 2:17

It's so interesting. I think the commonality that drives everything with the really thousands of singles that I've had conversations with at this point is that everyone wants love. We don't want to go through life alone. And I know that kind of probably sounds cliche and maybe overly sweet, but it's so true. We're wired for it. And I mean, I remember back to like studying psychology, and there's this famous study where there's um, you know, this baby monkey, and it has the option to either be with this fake mother who has like fur on her, it was like a like a metal thing, right? And has comfort versus one that has food. And like they chose the comfort versus something that was gonna for their survival versus the one with food. Like it's it's just we're wired to want to have that connection, to want to feel seen. And that's just the common thread. People are looking for different things and have different experiences. Is everyone going about it the right way? Of course not. There are ups and downs in the journey to finding love and of course in maintaining relationships, but it's so rare to meet someone who doesn't want to share their life with

Dating Apps And The Checklist Trap

Speaker 3:30

a partner.

Host Tea 3:30

Our human nature, for sure. What surprised you the most though about people when they start matchmaking through matchmaking services? What have you learned about them? In my sense, a lot of people don't know what they want. What's your experience on that?

Speaker 3:45

Yeah, I think a lot of people think they know what they want. And I think if you if you meet so many couples and they'll say, you know, if you would ask me to tell a matchmaker or tell anybody what I was looking for, a partner, who I ended up with, is so different. And I think that's where the magic of matchmaking really comes into play. Because yes, of course, we want to listen and honor what our clients are looking for, but it's also my job to pull out what really matters here. You know, I think sometimes people can get hyper focused on things that don't matter. Checklists. Yeah. And I, you know, I the dating apps have been used consistently, what, for like almost 15 years now. So my whole career as a matchmaker has coincided with the use, the popular use of dating apps, right? So I can't speak to what it looked like before then, right? But I do know that now it's like we're so used to just seeing a photo and making a snap judgment or deciding if we want to meet someone based on these stats that are available on an app or on a dating profile. How tall are they? What does their job look like? How do they look in their photos? None of those things actually matter long term. I agree. They don't. And it's baseline information, sure, but the apps are just rewarding this immediate snap judgment, 90% based on a photo. And that's where it's really skewed us to focus on the wrong things. And it's uh it's unfortunate, you know, people are not feeling great about that, right? Because we know that on the apps, 10% of men get 90% of the swipe right. That 10% of those men are consistently getting selected. And I speak to those men and they tell me they are overwhelmed by the apps, they are drowning in options. A man yesterday was just telling me I mean, handsome, tall, successful, emotionally attuned, like amazing in person too, not just on a profile. And he's like, Women are telling me they're in love with me after a second date. And he's like, and these are educated, accomplished women. That's what I'm saying. To him, and he's like, I'm just a normal, kind human being. And he's like, Is the dating pool lacking that much that he stands out so much? But I think one, it's because he's six, he's six foot three, right? And so right away you're getting more swipes, and so I think most women want guys who are more than six too tall. Right. We we gotta come to that's not lowering your standards, it's just opening up your pool, right? And so I mean, that's one thing right away, you know. I mean, most people are using the apps nowadays, right? And when you are only selecting that top 10%, it doesn't mean they're the top 10% best partners, it just means they're standing out the most on an app. It's really limiting your pool and it's making your pool extremely competitive. So when you open up the filters and think, okay, if I try dating someone who's maybe five, eight and seems like an absolutely wonderful human being based on what I know so far. Or, you know what? Yeah, this guy seems cute. If out of the 30 people I saw today, am I the most visually attracted to him? No, but he was great personality. I think there could be something here. And it's opening up in that way so that you don't end up with everyone else trying to get these top 10% of profiles. I think that's the biggest frustration. And that's where men get frustrated, because that's 90% of men who are just happy if they get any match when they when they could make wonderful partners as well. And so those are the biggest challenges that I see that are that the dating app culture have created.

Host Tea 7:12

Back to what you just mentioned. So all these top 10% of men, they're turning to high-end matchmaking services, even though they got so much attention on the apps.

Speaker 7:23

Yeah, it's interesting when when men come to me, sometimes they are in that in that top 10%, so to speak. And it's just analysis paralysis. They have so many choices. How can they possibly narrow down? How can they know if they're making the right decision? Oh, I see. They don't want to talk to all of these women. And so outsourcing to a matchmaker saying, Hey, can you interview these people, see who are the best matches for me, and really narrow it down so that I can focus on what's right instead of feeling like dating is this overwhelming, endless pool of options, right? Overwhelming, yes. It's like a blessing and a curse to be in that position, which but it's still easier than for someone who's on the apps and feeling like they're not getting any options,

The Real Work Of Compatibility

Speaker 8:06

of course.

Host Tea 8:06

How do you access compatibility beyond the surface level stuff we just mentioned earlier, you know, including even like career and lifestyle, all of that? What really matters?

Speaker 8:17

In terms of matchmaking, it's really a science and an art. I like when you how you described that, yes. Yeah. And it's, you know, there are the things that that matter on paper to someone, right? We have to have like a general age range. I'm not setting up a six-year-old with a 20-year-old, you know, we have to have something that's appropriate where you feel like you can understand each other. So there are the things on paper, but what matters most are the person's values. Talking about what do they see the future looking like? Do they want a family? What's that going to look like? What do they really value in their life? What does their lifestyle look like? Financial compatibility is so important. It's one of the biggest drivers of divorce, you know. So, so it's looking at what really matters where we know the person, we get to know their personality intuitively. This is where the art comes in. Intuitively, who do we see them clicking with? And that's just something that you really gain from experience over time as a matchmaker, where it's almost like being an actor when I have these video screenings for potential matches for my clients. And I kind of put myself in my head, like, how would my client be interacting with this person right now? Do I see them having that banter that they're looking for? Do I see them playing off of each other well? Do I see them having deeper conversations and being comfortable being vulnerable? So all that is kind of going in the back of my head while I'm seeing, do the big picture things line up as well? And so it's really when that alignment is there that it's like, yes, this is a match.

Host Tea 9:40

You know, everybody got their checklist. I mentioned earlier about this checklist, right? Um how do you feel about that? And I know you also do coaching, right? So is that the first thing you get to, like to assess their checklist and to evaluate whether their expectations are in a line, really? Help them find the one you want.

Speaker 9:59

Yeah, it's a great question. And this has been the biggest shift for me from going from working for a national company where I didn't get to select who I worked with. And for big, bigger national companies, you know, they have quotas to fill, there's sales pressure, all that kind of stuff. Yeah.

Host Tea 10:14

Yeah.

Speaker 10:14

You know, as long as someone's background check clears, they're probably going to take on any client, right? Whereas a smaller firm like myself, boutique matchmakers are more selective about who we work with. And so for me, there's more of a screening process before we even offer a client a package. For those exact reasons, we want to make sure that expectations are aligned. They know what we can really deliver on. I am not some magic genie who is like pulling a husband out of a hat. You know, it takes two people to build a relationship. And for my clients, I'm that collaborator to help them meet that person and to help them build a relationship. Selecting the right client is hugely important. And sometimes, unfortunately, I have to turn people down. If I feel like they have this long checklist that maybe doesn't exist and it doesn't feel like they're open to growth and open to reevaluating, you know, then I don't, I don't want them to waste their time and investment on a matchmaking service, right? Definitely. Sometimes people come to me with a checklist that makes a lot of sense. If it's 30 pages long, it's not going to make sense. But and when it becomes a more coachable moment, that's where we can dive deeper. You know, I've had people come to me saying, like, you know, I love skiing. I really need a partner who skis. Okay, like I understand why even just looking at skiing, there's so much nuance there. You're an expert skier, you're going down double black diamonds. Even if someone likes to ski, they may not be at your level. Even if they're at their level, you might be way ahead of them. They might be way ahead of you. It's not going to be this cute picture perfect thing going down the mountain together. Your helmets are on, you're not talking, you know. So then we kind of go into more like, okay, what is it about skiing? Well, I like someone who's adventurous. Okay, now we're talking about something that you really want to align on. Okay, you want somebody who has a sense of adventure. You want someone who's athletic, you want someone who says yes to new experiences. What is it about these ski trips that you really enjoy and where you really want to connect? Oh, well, I love the appre ski. I love when we get a drink and we get food at the lodge afterwards. Oh, okay. So what if she doesn't ski, but she would be happy, you know, to meet you at the lodge and hang out and go on the trip, but she doesn't need to be going down like these snow hills with you or whatever, these mountains. And then it's like, oh, okay. So now we've dug into like what's really under there. And so sometimes when I get these checklists that feel really specific, it's about what is the actual core value or what is the lifestyle alignment that you're really looking for.

Host Tea 12:43

Just a follow-up question on that is I just assume, like most of your clients, really, they do not end up being with someone who meets their very checklist, do they?

Speaker 12:52

Yeah. And that's an important conversation too, because you know, I have one client, I adore her, and she created a vision board of what her partner, what she wants her relationship to be like, including physical traits that she likes the most as well. Wow, awesome. She's like, I'm not expecting someone to have everything on my vision board. And so then it becomes, okay, so what feels like a good match for you, like is 80% of the vision board what you're looking for. But if someone came to me and it's like every single specific thing is what my future partner must look like, then you might be restricting yourself from meeting great potential people.

Host Tea 13:27

I

What Matchmaking Really Delivers

Host Tea 13:28

want to talk a little bit more about your industry, about matchmaking services. From what I understood, all of matchmaking services today is you do not guarantee results, right?

Speaker 13:37

In terms of guaranteeing a relationship, that's correct.

Host Tea 13:40

So that's really like also it's very expensive. That's stopping a lot of people like hesitating whether I should sign up or not. My question for you is what is a real success rate average in the industry today?

Speaker 13:53

My observation is like coming in and then starting my own firm and doing research before starting my own firm. I think there's a marketing problem in the matchmaking industry. Oh, yeah. Of course, people want to sell the dream that you're gonna meet the love of your life and go off into the distance, right? And that happens a lot. But you're right, it can't be guaranteed. And so what I think needs to be focused on more is what we're actually providing, introducing you to high-quality introductions, highly compatible people that are seeking relationships, getting all that time and stress off, having an expert and an advisor in terms of strategy, not just in the matches you're meeting, but in your life as a whole, and the opportunities for self-development, are there patterns you've been repeating that have been contributing to someone's struggles in dating? You know, all of that to me is the true value. And when you put all that together and it's a really good fit between the matchmaker and the client, and they have the right kind of network, that's when you're most likely to see success. And so for me, like my success rate now having my own firm, I know, is significantly higher than when I worked for a bigger company. It's not that I magically changed my formula. I think one is that I only work locally now. So I'm very much focused on community building and that's been essential. But the other part is, as I mentioned, is that I'm more selective about who I take on as clients. You know, if you take on a if someone takes on a client and they've never made it to a second date in their whole life, it's been rejection after rejection after rejection, and they don't want to do any work on themselves. They just think, oh, if you just introduce me to more people, it's gonna suddenly fix this. My success rate is gonna tank, right? So, what I like to do when I have individual conversations with people, I tell them, here's what my success rate looks like for someone like them. And it looks a little different for different clients.

Host Tea 15:42

So, for a local service like you, how long would it take a client to find the one they're looking for?

Speaker 15:47

Yeah, it can really vary. Um, for me, it's funny. I was just thinking about this the other day. The third match has frequently been a sweet spot for me. Uh-huh. There's people where it's taken much longer than that. Our most popular package in my service is six months of unlimited matchmaking, because we find that's a long time to introduce you to people. We pause when the person needs to pause to pursue something exclusively. If it doesn't work out, they come back. But I find that's the right amount of time to really extensively explore opportunities, different types of connections, and expand the network for them.

Host Tea 16:24

After you introduce a third person, most people will just be going out with that third person.

Speaker 16:29

It's happened a lot. Like if I had, I can't pick a number. Like I said, it's so different for different people. But I know I have um that's very high efficiency to me. It is. But I but I know I have a matchmaking friend, and she said almost all of her marriages were like the first or second match. Some people, it's later. It's so it's just we notice these patterns. And so that's just for me, is what I personally noticed in my matchmaking. Is like when I think of my long-term couples, I'm like, you know what? A lot of them, it was their third match.

Host Tea 16:57

Wow, that's amazing. Sounds like everybody should signing up.

Speaker 17:01

But again, I can't promise that. It's just a pattern I've noticed.

Host Tea 17:05

To be service and you don't need to swipe, you just sit around and wait.

Speaker 17:10

That's really the gift that someone is giving themselves to know that you're out enjoying your life, going on vacations, spending time with your friends, focusing on your career goals, and not having to come home at night and think, oh my God, I should have been swiping on Bumble.

Host Tea 17:23

And no, swiping takes so much time from people, it's also very insane.

Speaker 17:28

And all the messaging back and forth, and all of a sudden someone deletes the app or on matches, and you're like, what happened? Someone, everyone's been through it. And I'm I'm certainly not anti-app. I mean, they've given people more opportunities to meet more people than ever in history. But with it it definitely comes some very unique modern problems. Yes, that's what we're facing today.

Why Successful Women Face Scarcity

Host Tea 17:48

Yeah. I'm also very curious, Dara, what type of people, in your experience, do you find it often very challenging to find a match for?

Speaker 17:56

You know, I've spoken to other matchmakers, and I think this is something we see across the board. And it's that the more successful a woman becomes, the harder it is to match her for no fault of her own. Because what happens is that, you know, when men become more accomplished and successful, they become more desirable in the dating market, right? Whereas for women, it doesn't have an effect. Men absolutely appreciate an intelligent woman who has her own career, who is financially secure and not looking to depend on them. I hear that consistently from men. But to them, it doesn't make a difference if she's a teacher or a CEO. For the women who have, you know, reached that level of success and are and are looking for someone similar who feels like a peer in terms of a partner, you know, they're looking at this pool that's now become smaller, but for those men, their pool is bigger. And so that's what makes it more of a challenge.

Host Tea 18:54

How do you match women like that?

Speaker 18:56

So I find it just it takes a little more time. So typically, and not always, it really depends. But sometimes I'll tell, you know, some clients, I'll say, you know, we plenty of matches, it's going to be happening at a certain cadence. But for other women where I know we really need to hone in and make sure that it's someone who is not intimidated by successful women and actually, you know, admires that and loves the idea of being a power couple, you know, and gets excited by that idea. They're certainly out there. I just find that it takes more time. So with those clients, I typically say, you know, the cadence might be a little slower between matches because I want to be so selective on their behalf, knowing the challenges that come with dating for them.

Host Tea 19:38

And for a successful woman, when they're looking for a partner, they're looking for a partner who has the same level of success if it's not more successful than them.

Speaker 19:47

For the most part. And I think this is another area where we can open up because I think sometimes it can become too narrow. You know, like they need to be in this specific type of career for us to understand each other. And so again, it's, you know, work is a huge part of their lives, but it's like, again, let's think about what does life look like outside of work? What kind of support do you want from a partner? Because I think sometimes it's easy to go into this mindset of, oh, well, I need someone to like bounce business ideas off of and where we're gonna challenge each other and help each other rise professionally. Like, well, you've made it this far in life without having that. Do you really need that in a partner? You can do all of that yourself. You know, we we do need to factor in lifestyle because of course, you know, if you're from women, like they don't want to be paying for a guy to go on vacations to join them and do what they're already doing. So I know that's a big factor. Some, some care, some don't. It's very individual. So I think we kind of need to figure out like, what's the baseline lifestyle where we need alignment and kind of start there, but then really looking into okay, what do you actually want this relationship to look like? Do you need someone who's really going to give you new business ideas, or do you just want you just want someone to rub your feet and listen when you've been after you've had a long day? So that's what we're really looking for here. Someone doesn't need to have been in an executive position to be a supportive partner and understand where you're coming from. And so I think as long as we're open-minded about like what this person's life and career looks like, you're not looking to be on the board with this person. You're looking to have your life outside of work with them.

Host Tea 21:18

I'm just curious, just in general, about successful women, since we're talking about it. Most of your clients who are successful women, do some of them end up choosing a partner that are not as successful as them? Not career successful at all, maybe.

Speaker 21:32

Yes. And I would say, in terms of like financially, yes. Yeah. The consistency I see is that both parties have some kind of passion and ambition and drive. Um, but for example, I had a client, she was a, you know, very accomplished physician. And really, she actually came in saying, It really doesn't matter to me how much money somebody makes. You know, she's brilliant. She's like, you know, I need someone intellectually compatible. That's hugely important. And of course, as a physician. She's really passionate about helping her patients and making a difference in their lives. We ended up introducing her to someone who was the director of a nonprofit. And so, of course, the nonprofit world, it's not the same kind of financial return, but it's incredibly admirable work. They really wow. I can see that can be a good match. Exactly. Yeah. Wow. Good find, Vera.

unknown 22:19

Thank you.

Speaker 22:21

I like the story. Again, it just really comes down to like what matters underneath it all, underneath the superficial of like what's on your W-2, right?

Chemistry Myths And Three-Date Rule

Host Tea 22:30

What are the most common reasons that promising matches fail after first or second dates?

Speaker 22:35

So with matchmaking, you know that things align, right? We know the things that matter are already there. What it really tends to come down to is chemistry. Yeah. And this is like the most frustrating part of being a matchmaker. Chemistry, yeah. Yeah. When you put two people together and you're like, oh, I'm really excited. And then maybe one person after the first or second date says, sorry, I'm just like not seeing, feeling the romantic chemistry, you know? Yeah. What do you think about that? It's so interesting to me that people can feel so confident in that choice. Because again, like we mentioned before, how many couples that have been together for decades do you meet? And they're like, oh yeah, like we met at a party or like a friend's house, and I wasn't really feeling it. But then we saw each other again. And it's like this repeated exposure where they start to see them in a new light. I mean, for me, I was friends with my husband for seven years, never thought of him romantically. And so I think we need to take the pressure off the chemistry. And again, I think I totally agree. And again, this is why I'm curious like, is this something that we're seeing more of because of app culture? Because people are just so used to like seeing a picture and making these snap decisions that it's then translating into their dating life. Or I need to know after spending two hours with someone if I'm romantically interested in them. So instead, I just want people to like forget chemistry in the beginning. I mean, look, if you're repulsed by someone, like by all means, don't see them again. But if you walk away from your date and you're like, this is a decent human being. And I want you to think, what do you admire about this person?

Host Tea 24:03

Do I want to go on a second date with this person again?

Speaker 24:06

Yeah.

Host Tea 24:06

I think that's the only thing you should be finding out on first date. Do I like this person enough that I can hang out with her again?

Speaker 24:12

Because chemistry can grow over time. And if someone totally agree. And if someone wants such a long relationship, it takes work to sustain that chemistry too. Yes. You know, I've I've been married for 10 years now, and I still think my husband is the cutest thing in the world, but it doesn't have to do anything, maybe a little bit about how he looks. I mean, I think he's cute, but but more than that, like the attraction for me is like, how many times has he been there for me, been there for our children? I can always respond on him. He makes me laugh. We have fun together. I wouldn't have known any of that after a first date. Those were things that like we learned together over time. And so it's that repeated exposure. And so I think when the values align, when the things that matter really align, it's always worth giving it at least three to five dates to see how that chemistry develops. Because more often than not, when that's there, you're going to become more interested in someone over time.

Host Tea 25:06

That's totally fair.

Speaker 25:07

I'm glad you're applying this to your life too.

Host Tea 25:10

I completely agree. On the other side, two friends, two long-term friends can suddenly fall in love too, right? It just reflects chemistry on first date is not that important.

Speaker 25:20

Yeah. Or you think of, you know, work used to be a commonplace where relationships would start and and how many growing over time. Yeah. Even when you think of friendships, you know, coworkers, where maybe at first you're like, oh yeah, they're nice. I don't know. And then they end up becoming your best friend over the course of a year because you spend so much time together. And the more we spend time with people, the more we find things in common.

The Traits That Last

Host Tea 25:43

What are some top three qualities you wish more people focus on when selecting their future partner?

Speaker 25:49

Number one is self-growth. Gross mindset. That's a growth, a growth mindset. That matters. That has to be number one. And there and there are things that you can pick up on in the beginning to see if that's there. But you know, if you're gonna have a long-term relationship with someone, you're both going to evolve over time. But also being in a relationship, you have to inevitably point out things in the other where whether you need them to communicate differently or show up differently to meet your needs. And if someone has a fixed mindset, it's just a non-starter, like I'm not changing for you. And it becomes self-defensive versus someone with a growth mindset. Who is also is open. Yes, exactly. Like they know they aren't perfect, they know that they can grow and change in certain ways to be a better partner and to be a better person. And so that's number one. Number two sounds so boring, but uh being reliable, you know.

Host Tea 26:45

Well, being reliable is important in any relationship. I would just say that.

Speaker 26:48

Yeah, I think it's so important. And then number three is kindness because nothing else matters if you aren't a kind person.

Host Tea 26:56

I think for both men and women, we all value kindness in a similar level.

Speaker 27:01

And all three of those things you can certainly recognize when they aren't there on a first or second date, if someone is is rude to you, not appreciating your time, you know, saying, like, oh, I'm like running an hour late, or oh, I have to cancel. And, you know, if people cancel once, okay, but if it's a pattern, then the reliability isn't there and you can't count on them. For the most part, people are gonna show up well, and you really aren't going to know those three things until you've spent more time with the person.

Host Tea 27:27

Here it goes with another question to hit me. What's the most underrated quality that predicts a strong long-term relationship being underrated?

Speaker 27:35

I think what's most underrated is the relationship that we have with ourselves.

Host Tea 27:40

Oh my goodness. Wow. I did not see that coming. That is actually the most important.

Speaker 27:47

Yeah. If you're feeling insecure, you're gonna be projecting that onto your partner and needing more fun and making everything harder. There, there's so many things. So there's, of course, there's no perfect person. We are all forever a work in progress. But the more, just as a lifelong journey, you know, again, the growth mindset, the more that we work on ourselves, the less we need from a partner, and the easier a relationship becomes. You impressed me on this one.

Host Tea 28:13

Okay, oh, good. But it's also the big truth. After helping so many people, finding love, what has matchmaking taught you about relationships?

Speaker 28:23

It's taught me that really it ties back to what we were just talking about. It's iso important to find happiness on your own and to enjoy your life, but just know that it's it's sweeter and better and more enjoyable with a partner to be a witness to your life, to be a source of support, to go and have vacations and adventures with. And it's really, I just don't think there's anything that matters more in life. Not just romantic partnerships, I mean all kinds of relationships with our family, with our friends, like and and ask my clients to think, you know, when you're 90 years old and you look back on your life, what do you think are you going to remember? What are you gonna value the most? And it always comes down to our relationships and the quality of our relationships. The most important thing in our lives as human. Yeah, and I think it's so easy to look lose touch of that in this busy capitalistic society. Yeah, you know, we'd all be better off if we remembered like the reason we're here is for connection.

Host Tea 29:22

Yes, yes, we are. I'm also very

Stories From The Matchmaking Trenches

Host Tea 29:24

curious. Are you able to share a matchmaking story that you're most proud of throughout your entire matchmaking career so far?

Speaker 29:32

The first one that popped in my head is a recent story involving a 70-year-old man and a 68-year-old woman that just um it just makes me so happy that they found love again and are having such a great time together.

Host Tea 29:45

Wow.

Speaker 29:46

There isn't one I can pick that I'm most proud of, but let me just think from the last year. Um, I can think of a woman in her 30s who came to me, again, like busy, accomplished professional, felt like she would get to that three to five date window and it would fizzle out, either experiencing a lot of rejection. And we really kind of uncovered that the pattern that kept happening was that she was falling into these people-pleasing tendencies and not being her real self in a relationship and not really communicating her needs and just kind of trying to be that girl that just goes with the flow and makes things easy. But then one, like the person isn't truly getting to know her. And two, then she was attracting the kind of guy who just wants a woman who will just placate him and go along with everything and can't handle being challenged, right? It wasn't leading to the right kind of connections. And so we really had to talk about how to get past that. And it was really hard for her at first, and then it was like she did it once, and we like prepared this whole conversation she was gonna have with someone. And it was funny, it was the third match. This one, there's more to the story, but um, the third match with her ended up being turning into a relationship. And there was a lot of coaching behind the scenes because you know, there was a bit of a communication breakdown. And instead of just before, she would have just stayed quiet, right? And just let the relation go on and on and on.

Host Tea 31:05

Well, she has you, so you provided a guidance.

Speaker 31:07

Yeah. And so in the beginning, I was really saying, okay, this is what I want you to say, and like kind of giving her a script that she could work off of in a way to really prepare for some of these tougher conversations. And even just doing it once or twice was so empowering and realizing, like, oh, wait, when I express this, I get what I want. I don't push people away. They actually understand me better. And it like, it eradicated that fear. And so for her, it's like no matter what the outcome was, that was such a huge shift in her life. And I was so, so proud of her. And so what ended up happening is once she was communicating her needs a couple months in, she realized, okay, she's made everything really clear. And unfortunately, nothing wrong with this person, lovely man, just wasn't right for her. And so she ended the relationship instead of letting it drag out for six months, right? Yeah. Breaking up with someone when you need to is the right step.

Host Tea 31:55

Yes, definitely.

Speaker 31:56

She took a couple weeks just to kind of regroup, and then she was like, okay, I feel ready to get back out there. And then I think it was about two months later, she met the guy who is now still her partner, and they've been together, I think it's been about six months now. Cause this was and now, like, she, yeah, it's the best, she just had the best relationship she's ever been in because from the get-go, she was just able to communicate so transparently, and that made her so much more magnetic as well and more attractive versus just being the sweet person because it was kind of boring. That was the fact that that's the feedback I got after her first date. Is she's very sweet and nice, but like kind of boring. And this is not a boring person, but that's how she was coming off when she was so afraid of rocking the boat and really authentically being herself.

Host Tea 32:36

Fear plays many people's dating life, so that stops them just being authentic. Yeah, exactly. And if you're not being authentic, it's hard to lead to anywhere meaningful, right?

Speaker 32:48

Exactly. And I think especially a lot, you see it a lot with people who are new to dating, try to be like sweet and polite. And of course, we're all we're all kind, you know. But it's it's the things that make you quirky and weird that make you stand out, that make someone want to connect with you. So it's like, let's stop being boring.

Host Tea 33:05

I like that. What does a truly successful relationship look like from your perspective after seeing so many matches played out?

Speaker 33:13

Both people feel comfortable completely being themselves in front of the other partner while simultaneously challenging each other at times to become the best version of themselves. Because I love it. I think that's what a good relationship does. It pushes us to grow where we need to grow. And grow together, right? Exactly. And I think I love relationships that we call like builders, where it's two people that kind of have the shared vision for life that they're working towards together and have shared goals. I find those relationships to be really exciting and rewarding and it and it keeps you tied together as you, you know, of course, appreciate the present, but while also like building towards whatever your dream life looks like.

Host Tea 33:56

I feel each one of us are dreaming about that type of relationship.

Speaker 34:01

People can do it on their own, but it's a really good feeling to share that with someone. Just need to be patient, patient and strategic.

Host Tea 34:07

I like that, definitely. Otherwise, you get exhausted so easy. Yeah, yeah, that's true.

Mindset Shifts For Dating Burnout

Host Tea 34:13

Sarah, if someone listening right now feels exhausted, stuck, or even discouraged in dating, one mindset shift or action, you'd recommend they start today.

Speaker 34:25

Two pop in my mind right away that we already kind of touched on. One is when you're going on dates and meeting people, you know, I think one thing that can make dating exhausting is when we go on a date and we're just looking for red flags. We're looking for what's wrong with this person. We're trying to predict why it won't work out based on all of our past experience. But I find the people that approach with that mindset and get burnt out the most quickly, right? Easily, yeah. Yeah. And if you see a red flag, of course, like acknowledge it and move on. Um, but we don't need to like dig for these things, especially on a first date. So I like I want people to have fun. I want them to just focus on connection. It's impossible to know if someone is the love of your life after a couple of dates. All you can know, you can know, no, no way. All you can know is you can enjoy time with this person. So that's all I want you to focus on is like getting ready and thinking, how can I enjoy myself with this person? And instead of looking for all the things that could be wrong, think what do I admire about this person? What am I curious to know about this person? And and then you're gonna train your brain to have a better experience. And then the other part is I mentioned when you're 90, right? And so, you know, if you're getting ready, if you like, let's say it's like a Thursday night and you have a date and you're like, it's been a long day. I don't, I don't know anything about this person. What am I doing? You know, I'm tired. I'd rather be in bed. I've been on there. That's that's what I want you to channel your future 90-year-old self. By then, most of us are are alone again, statistically. And so I just want you to have a conversation with her. She's like, You can still put on heels. Oh my goodness, look how good you look amazing. Forget your date for a second. First, just enjoy how fabulous you are, right? And now, wait a minute, you're gonna go out, you're gonna go out to dinner and meet a new person, a stranger, and they want to know it all about you. And you make it sound so exciting, right? That's but you can do this. You can do this with your own, with your own brain, your own internal monologue, and like and just think, what is your nine-year-old self saying? She wants you to go and have the best time and make the most of this date and don't just be in this moment because she's in the future. She already knows it all works out in the end, right? She's over there with her grandbabies, and she's like, trust me, it all works out. I want you to go out and I want you to have a great time.

Host Tea 36:46

That's awesome. Thank you so much, Dara. Of course. I hope that's helpful. It's awesome. I totally enjoyed it. And some answers from you are unexpected but great answers.

Speaker 36:56

Oh yeah.

Host Tea 36:58

Thank you so much being on this podcast.

Speaker 37:00

Yeah, it's such a pleasure. I really enjoy chatting with you.

Final Takeaways And Subscribe

Host Tea 37:04

There's something Dara said that really stayed with me, that chemistry can grow over time. And I think that's such a powerful reframe, especially in a world where we've been conditioned to believe that if it's not instant, it's not meant to be. I believe that connection is more about alignment, curiosity, and a willingness to truly get to know someone step by step. And sometimes that person might surprise you. If you take anything from this episode, let it be take a moment to reflect on your own values, expand what you're looking for beyond the obvious, and don't underestimate the power of showing it out authentically, even when it feels ownable. Because at the end of the day, like Dara said, we are wired for connection. The goal isn't to win at dating. It's to create something that actually feels good, grounded, and real for yourself. If this episode resonated with you, please subscribe, leave a rating or review, and share with someone who's navigating dating right now. And if you want to check out Dara's work, you can find our information in the show notes. Thank you again for tuning in to this episode of the dating chat. I'm your host, Tea. Until next time, keep showing up. Stay kind, stay curious, and never settle for less than the love you truly deserve. See you in the next episode.