One of Chicago’s leading matchmaking companies is Stef and the City, owned and operated by Stef Safran. Not only does Stef work hard to create lasting romantic matches, but she’s also a dating coach and offers several unique resources to help singles date better and find love. Recently, our VP of Partnerships Matt Seymour got an opportunity to interview Stef Safran about her work with Stef and the City. We’ve included the video and transcript of that interview below for you to enjoy!
Full Stef and the City Matchmaking Interview Transcript
Matt Seymour:
Hi everyone, this is Matt from Healthy Framework. Today I’m very excited to be joined by Stef Safran, owner of Stef and the City.
Stef, thank you so much for joining today.
Stef Safran:
Thanks for having me.
Matt Seymour:
Absolutely. So let’s jump right into it. Can you tell me what separates Stef and the City from the rest of the matchmaking services that are out there?
Stef Safran:
Well, one of the things that I do a little bit differently is the way that I approach it for both men and women, because there is a difference in how men and women date. So I only take on men for what I call proactive matchmaking services. What that means is the men are paying me the big bucks to do the search as though I was a recruiter. But the women also get some of the same respects in terms when I’m matching them. They do have a piece of the pie. They do pay a much smaller amount, but they are paying to meet with me and they are paying to get the same information about the match that the men do.
And what people like about that, particularly the men, is they like to know that the women have a say in it because they don’t want to just be matched up with people who are hoping maybe, well, if I go out with this guy, she’ll set me up with more guys.
And that’s number one. Number two, I really do focus on the idea that a lot of people need dating coaching, but not for the reasons that people might think. It doesn’t mean you don’t know how to date. But most of us are not looking for entry level dating anymore. And what that means is the people who are giving advice, if you were to go and ask somebody, “How do I go and meet people,” they’re going to give you experiences that could be 15 years old. They’re going to be saying… I mean, who’s going right now and checking for jobs in the paper? That’s what I did back in the day. Who’s looking for jobs on Monster? Monster? No one.
So when people go and look and say, well go try this app or this site, it’s also based on location. So let’s say the app itself is based out of San Francisco and you’re in Chicago. You are not going to get the same level of attention. And so a lot of people get very frustrated because they take it very personally because we’ve gone into an age where we think everything’s Amazon Prime and we can order it instantly. And people don’t like hearing, “Well, this might take a little time because we need to put your best foot forward and we need to have your action plan so when you do meet somebody, that if that person doesn’t work out, you’re going to bounce back quicker and go back.”
And for many people, really what they’re looking for, the reason they’re looking to meet somebody, is that they miss the companionship that is not just of a romantic relationship, but of a friendship.
Matt Seymour:
Yeah.
Stef Safran:
So for a lot of people, if they have good friends that they can relate to at this point in their life, the romantic relationship takes a backseat and isn’t the primary focus. And that’s what I say is the dating coaching component, because most of us do not have a way of making new adult friends that isn’t on text messaging.
Matt Seymour:
Yeah, no, that makes sense. And that was a good parlay, I think, into this next one, and you touched on it a bit because wanted to inquire the ideal customer Stef and the City’s designed for. It sounds like primarily men, but it looks like you touch on both then, if I’m not mistaken.
Stef Safran:
Absolutely. The ideal customer, I’m going to say, is anywhere from twenties to fifties. And for people who have just moved to the area, they could really benefit from my coaching because I’m going to explain, well, let’s come up with the best marketing plan for you. So somebody who’s just out of school and says hey, I moved to Chicago, or I’m leaving from a suburb, or what do I do? How do I meet people?
So it isn’t just… The coaching aspect is more affordable for more of an average person, whereas the matchmaking is more for somebody who has gotten more experience and may need somebody to do it for them in a way that… Look, a 25-year old doesn’t need my… Has more options.
And as far as women goes, I’m very good with helping women as well. It’s just that I don’t want to waste anybody’s money and spend five figures to do matchmaking when I can’t just walk up to men and be like, “Hey, you’re six feet. Would you date a five-one woman?”
Matt Seymour:
Right, right.
Stef Safran:
Now, you can flip it on the other side.
Matt Seymour:
Yes.
Stef Safran:
But I’m going to say that the best customer is going to be willing to listen to me, what I call the 80% rule. You can throw out 20% of what I tell you. You don’t have to agree with it. And you’re going to give me an 80% commitment of the things I’m asking you to do.
We’re going to throw a bunch of different things because there is no magic one-size-fits-all. So the easiest way I can say is the customer that is willing to work with me and willing to do the homework and willing to listen to me at least 80% of the time, that would be my dream customer.
Matt Seymour:
Perfect. I like it. And you’re doing great with the segue on the questions because you just touched a bit on price point. And something that we hear often is concerns for folks that haven’t hired a matchmaker before. So something that’s pretty clear is that hiring a personalized matchmaker like yourself or some of the services you provide is more expensive than using your traditional dating app, let’s say Hinge Tinder or anything along those lines.
How would you rationalize those costs to somebody that might be concerned about the higher price tag?
Stef Safran:
Well, you made it really easy for me. Talk about timing. Match.com, which basically owns every dating app now, is now offering a premium service for about $500 a month. Guess what? You can spend $3,000 for my coaching and I can give you a lot. I bet you I can get you a lot more personalized attention and dates if we work together, and my cost is 3000 and we have an action plan that is much more detailed than maybe this curated $500.
Now the other situation is with as far as the matchmaking goes. Sometimes when people come to me, the 10,000 plus price tag sounds high to them. And maybe when they find out what the coaching entails, maybe the coaching is enough that I say, “I’m cheaper than therapy and I can get you results. And I can also give you new best friends, and you get unlimited new friendships.”
So sometimes these friendships are the places that are going to help you actually meet people to date. Even on the idea that these people on the apps, your nameless, faceless, sometimes these people, you start getting to know them through other things that you do and then you can be like, “Oh wait, I saw them at this event I went to and they’re single?Now I can hit them up, because I’ve actually met them.”
And when people find out when you’ve done the homework, I am definitely very fair price because there are some places that won’t even start talking to you until it’s 25,000. But the idea that free is good, look where it got us so far.
Matt Seymour:
Right. No, that makes sense. And a very solid explanation in terms of justifying the expense and things there with it.
Shifting gears a little bit, would you say if somebody’s interested or thinking about a matchmaker, are there any potential drawbacks to using a matchmaker that people should be aware of?
Stef Safran:
Well, I think one of the things people have to understand is that a good matchmaker is going to be honest with you, and they’re going to tell you things. I tell people generally to stay off the apps, for example, between Thanksgiving through New Year’s, because a lot of people who are not so happy are going to be on there. So the same would apply if you want to start with a matchmaker and we say to you, “Hey, I’m going to need a little bit of lead time.”
You’re not going to go out with someone next week. You’re not going to get a million people like maybe you’re used to. You’re going to pick through all these piles. What I explain to people is we need some time to make sure that also the people I’m setting you up with, I get enough feedback so that we are not wasting matches just to, again, rush you to have a date for a wedding or something.
So I think the drawback is people think that we make magic people, and the reason my prices have had to go up is I deal with the same flakiness you guys deal with. But I’ve been charging for my meetings forever, so I know now. And for the people who didn’t and they’re like, “Well, but I don’t want my time wasted.”
So I think the biggest drawback is people have to understand that, again, just because I introduced you to somebody, it doesn’t mean that that is going to be your forever person. If that was the case, The Bachelor wouldn’t have a bunch of divorces. They really focus on it.
But I do believe that a good matchmaker will be honest and want to invest time making sure that you’re dressed okay, making sure your conversation skills, making sure that you don’t go into it negatively. I put a lot of my gentlemen on practice dates before we go out and I get a lot of fighting with me, but ultimately they get it and I send them to a stylist. I’ve had men do their eyebrows or their hair or anything.
And I keep saying that these things are temporary, but we want to get you past the first interview. So I think the tough thing is it’s an emotional process. There are no guarantees. But if you do listen to at least 80%, I really do have a good corner on getting people into relationships, whether it’s through my coaching or through my matchmaking.
Matt Seymour:
Excellent. No, more wonderful feedback there.
Shifting a little bit more there, and I know you’ve touched on bits and pieces of this through some of the other answers, but would you say there’s anything unique about the way that you might find matches for someone?
Stef Safran:
Well, since I’ve been in this business for a long time, I started out getting matches for a show called The Dating Game. I’m not completely that old where it was Arnold Schwarzenegger time. But what people might not realize is I lived in Los Angeles and when people were getting people for these game shows, a lot of the people who’d go, when I do say Arnold Schwarzenegger and some of these other people, that was used as a way into the entertainment industry.
So you were dealing with a lot of models and people who were looking for more than just a date. So I do have experience where I literally would go to the clubs and get people in that regard. Then I worked for another company where, at that time, you would wear little black dresses and go to multiple places as well. So I’ve seen this go through different transitions.
I also went to a matchmaker and I said, “I could do a better job.” So I do have some of that personal experience, but what I do do that’s unique is I’m a very good networker. And so I look at each and every opportunity. I was at the gym this morning. I saw a woman, gave her a compliment. I mean, it’s a shocking thing. And she told me that she was a biker. Well, I’m a biker.
So I told her, I said, “Are you single?”
And she said, “Yeah.”
I said, “Well, here’s my card. If you’re interested, I know of some biking groups I can tell you about.” Now that’s not the hard sell because is this somebody I could work with? I know other matchmakers. But the thing was is I look at this and… Again, I’ve had people call me up and say, “oh, I’m so ready,” “Oh, I met somebody.”
And then they call me six months later. “Okay, it didn’t work out.”
This is par for the course. I don’t get mad at people when they say they met somebody. I just say, I’ll take you if it doesn’t work out. I had one guy, another Matt of course, because a lot of my clients right now are named Matt. Not giving much away, because they’re all Matt.
But actually he told me the description. He was in his twenties. I said, “I’ll see you in three months.” And I was right on. And then he dated somebody else while we were working together and I said, “This is going to last six months.” Six months later, yeah, and we were working together at that time. And so ultimately I was able to give him some predictions about… Everyone thinks they’re unique in dealing with their problems in the romantic field.
Everyone’s coming to me because something’s broken, not because it’s fixed. So the objective here is it’s not just about meeting that person. It’s what if you find out that this person is not right for you? What are your bottom lines? Because there are people who spend too much time with people that there’s chemistry, but there’s no future. And there’s people who say, but this is my drought. It’s been so long.
And so we also have to come up with, well, what are your things that you need to stay away from? If you know you’ll drink a little too much, don’t do a drinking date. Or if you don’t want to bring things into the mix about any sort of romantic entanglement, don’t go out on a Friday or Saturday night right away.
That’s okay. There’s no hard and fast rule about what is a specifically good date, but the rule of thumb is the length of time that you spend with somebody is not equivalent to how interested they are.
Matt Seymour:
Yeah, that makes sense. Something that I’ve been interested in, it’s been fun talking to some other matchmakers and things to see is, have you struggled before to find an ideal match for a client? And if so, what’s your process when that happens?
Stef Safran:
I don’t think there’s any matchmaker that hasn’t struggled with this. Number one, I’m part of what’s called the Matchmaker Alliance, which is a group with international ties. And I know other people in the business. I have a business partner I work with who is in Chicago. We both hit on different types of matches. She will call herself the Geriatric Matchmaker, which is pretty popular, I guess, with the Golden Bachelor.
And I had stated that I’m in the twenties to fifties mark, she’s like fifties and up. And we’ll work together. That’s one option is to have another matchmaker work with you. Another is to put out a casting call. And another is to go across some social media, ask a few people who you know are people who are the introduction-istas in your world.
I have a real estate guy, he always knows great single people. And then I go back and give him some real estate. These are people that might be on the market. But I will tell you, I certainly have had people that have come back to me after I have set up somebody that they liked working with me, even if it wasn’t the right person. And then they brought their friend in and I got their friend married.
And I’ve had clients that use me as a matchmaker and then, okay, they didn’t meet their match and everything but their advice brought way to… They credit me with finding their partner. And I’ve always been surprised at some of the men that I thought, for sure, oh my God. They don’t want to work with me or whatever. And then they were the nicest people when it came down to it.
They said, “Well, Stef, you really gave me some information I didn’t have.” And I’ve had people that came back to me that disappeared for a few months and I found out that’d gone online with the advice I’d said, and they met their partner and they were telling me they were engaged to be married.
So I wish I could say I was invited to all these weddings. I’m not. But because again, there is a little bit of embarrassment on some level still, but the thing is at least they’re coming back and telling me, “Hey, I credit you.” And I got one about three weeks ago and I worked with her in 2018. And it really felt wonderful to wake up on a Monday and hear that she had made it to the other side.
Matt Seymour:
Yeah. Oh, that’s great. And that all makes sense there.
Something I was interested in. I spent a very small amount of time in Chicago myself, but your services mainly available there. Would you say that there’s anything unique about dating in Chicago that you’d be able to share with us?
Stef Safran:
Well, I’ve lived in Madison, Wisconsin for college. I’ve lived in the city for over 20 years at this point. And I’ve also lived in Los Angeles. So I think everybody thinks that wherever they’re living, it’s harder to date.
And what I’ve noticed is from living in the city and living in other places that are city, it comes down to if you match what the city is like. So let’s say you are very religious and conservative. That’s not what a lot of the city is. That might be the surrounding suburbs. So what’s going to make things easier or harder is based on are you living in the right location for who you are and the types of people you want to meet?
Not just in the dating world, too. There are challenges when people live with their parents, which they do, and they don’t realize it because they’re like, well, once I meet someone, I’ll live with them. And it depends on the age. If you’re 25, it’s normal enough. But if you’re 35, when are you moving out? And I do think the challenge is that there is a lot of opportunity. So you might find that people might be a little flakier because you’re not in Michigan or Indiana where there’s a smaller pool.
So the bigger the pool… It’s The Paradox of Choice, which is a book out there, that you go to a grocery store and you have all these selections. It doesn’t make it easier. A lot of times it makes it harder.
Matt Seymour:
Yeah, that reminds me, the Cheesecake Factory menu every time I go, which it’s been a while. It’s overload.
Stef Safran:
Lettuce wraps.
Matt Seymour:
With it. Well, excellent. So to close, one last question, which is one of my favorite ones always is to see, is do you have a favorite success story that you’d be able to share with us?
Stef Safran:
I do. I have quite a few, but one stands out to me that is more relevant now than it would’ve been. And I had a client that came to me. He was about 35, and he had lost his wife to breast cancer.
And at the time, this is probably about 15 years ago, this was not something you heard of as much as people losing people and being younger and widowed. I think if he would’ve gone online, he might’ve had a lot more issue because, at that time, I think apps were not the big thing, but sights were. And people just still had this idea, well, this person still…
They didn’t have children together. And basically I set him up and his fourth match was his wife. And it was really nice to hear that, again, when you have the ability to talk to people personally and being like, “Look, checked his house, there’s no memorial. The other side wants him to meet somebody else.” When you have that ability to give the reassurance, that is somebody who might’ve had trouble online.
And I’ll throw in one more. I had a guy, five-six and chunky. I thought for sure, this guy, I was about to take him out and do a bunch of coaching. And I had another guy who was six-one, really good-looking, in shape, and I was going to set up this one woman with him. And all of a sudden he’s like, “Yeah, she’s 10 pounds over the one I want,” whatever.
So I call her back, I’m like, “Look, I’m really sorry, but this guy, it’s not going to work out. I do have this other guy, and here’s his story. He is a little chunky and he’s five-six.”
And she said, okay. She married him.
Matt Seymour:
Wow. Yeah. I think sometimes we have to get out of our own way, so to speak. We might have these preconceived notions, but you being the professional and the matchmaker can help steer folks.
Stef Safran:
Well, here’s the thing. I thought she would say no. She surprised me. That’s what I’m saying. I thought, oh, if I have to put my bets down on who are going to be the people who are going to married and who are going to be the easier people, I’ve been wrong. And so my thought was I was prepared for him, because I think this is match five or six. I was so prepared. I was like, we’re going to do this and we’re going to do all this coaching.
And lo and behold, she’s like, “Sure, I’ll meet him.” And the next thing I know, she’s super happy. And I wasn’t expecting that. So sometimes it’s really nice when you basically don’t plan. That wouldn’t have been who I would’ve put to set him up with, and it worked out.
Matt Seymour:
That’s amazing.
Stef Safran:
So I would say that just like everybody else, we don’t always know what’s going to work, but what I do know is you have to figure out how you’re going to deal with any of the challenges you face. Because no matter who you’re going to meet, you’re going to face challenges.
And if you’ve had the foresight to already prepare and say, look. Around three months, this is when all my relationships don’t work out. Well, what can you do differently? And again, I tell people, don’t get naked with anybody unless you’re going to be in a relationship. And then still, don’t do it too early because you can’t go backwards.
So if that means doing things on a Thursday night when you have to go to work the next day or doing a day event for quite a few weeks, people have to be more intentional about what’s best for them.
Matt Seymour:
Yeah.
Stef Safran:
Because nobody knows you, better than you. And I can help you, but at the end of the day, there is still responsibility on you to make sure that you stick with those things that are important to you so that you don’t say, “But I invested two years in him.”
Well, you shouldn’t have invested two years if you’re unsure.
Matt Seymour:
Yeah.
Stef Safran:
25 is very different than 35. So I will just say that I always say this. Everybody who comes to me, whether they’re the prom queen or the nerd, has the same issues at the end of the day. They haven’t found the person that they want to be with.
If you’re attractive or if you have to lose weight, it doesn’t mean you’re going to have an easier or harder time. Sometimes things are really the luck of the draw. And people have to be open to understanding that everything’s not personal. Dating sites, they’re still companies.
Matt Seymour:
Yeah.
Stef Safran:
They’re still trying to make money off of you.
Matt Seymour:
Yeah, no, that makes sense.
Well, really appreciate all the insights today. It was great getting to learn about the business and more about you. Definitely, thank you again, Stef, for joining. Appreciate the time. Excited to maybe check in, do a future interview again in another three, six months or something, but would love to stay in touch.
But thank you so much again for joining and take time to help us understand a little bit more about Stef and the City.
Stef Safran:
Thank you so much for having me. It’s a pleasure.
Matt Seymour:
Sure. Thank you.