Andrea McGinty built what many people would call the ultimate success story: a booming global business, a high-profile marriage, and great kids. So why did midlife still ask her to stop and reconsider everything? Andrea talks about what it feels like when the life you built no longer matches the person you have become. We talk about intuition, values, second acts, and why clarity often arrives slowly, quietly, and from the inside out. If you have ever wondered whether it is possible to change course without burning everything down, this conversation will resonate deeply.

Guest Bio

Andrea McGinty’s journey is as compelling as the love stories she’s helped create. After being dumped at the altar in her 20s, founding It’s Just Lunch Matchmaking in 1990 (before Google and online dating), and later navigating divorce after 24 years of marriage, Andrea took a four-year pause from dating to focus on raising her teenage daughter. When she decided to jump back into the dating world, she approached it strategically, and it paid off—her sixth first date turned into her husband, whom she married in Rome in 2024.

As the founder of It’s Just Lunch in the 1990s, Andrea revolutionized the matchmaking industry. Her innovative service grew to over 110 locations worldwide and facilitated over 33,000 setups, resulting in more than 10,000 marriages. Today, her company, 33,000 Dates, focuses on helping the over-45 crowd find love in the second act of their lives. Currently, 65% of her clients are in long-term relationships, a testament to her expertise and unique methods.

Often referred to as the OG or “Godmother” of modern dating, Andrea’s impact extends beyond her clients. Like an NFL coaching tree, more than 40% of today’s top 25 matchmakers trace their roots back to Andrea’s mentorship and pioneering techniques. Her influence has shaped the industry, creating a legacy that stands out in the world of matchmaking.

Andrea’s work has garnered extensive media attention. She has been featured on Oprah, People, Today Show, and named Entrepreneur of the Month on the Early Show. As a sought-after speaker, she has addressed audiences at the American Marketing Association and other prestigious events. Her insights and passion have made her a trusted voice in the realm of love and relationships.

With over three decades of experience, Andrea doesn’t just write about dating; she’s lived it. Her latest book, 2nd Acts: Winning Strategies for Dating Over 50, combines personal anecdotes and professional expertise to guide singles on finding meaningful connections later in life. Andrea’s vibrant, no-nonsense approach continues to inspire and empower those ready to embrace their second act with optimism and love.

Turning 40 and realizing success is not the same as alignment

Andrea McGinty built one of the most successful dating companies in the world before most of us had email, Google, or any idea what online dating might become. But by midlife, the business she had poured herself into, along with the marriage built alongside it, no longer fit who she was becoming. Andrea shares what it was like to grow up as the oldest daughter in a big Irish Catholic family; launch It’s Just Lunch with $3,000 and a dream;, navigate public success alongside private fear; and ultimately listen to the quiet inner voice that told her it was time for something different. Her midlife transition includes selling a global company, divorcing amicably, facing cancer, and stepping fully into a second act built around values, alignment, and deeply personal fulfillment.

Episode Highlights

1. Growing up as the oldest child in a large Irish Catholic family and how responsibility and resilience shaped Andrea early on
2. Launching It’s Just Lunch before online dating existed, and how sheer scrappiness, intuition, and grit fueled its success
3. The emotional reality of early entrepreneurship: outward confidence paired with constant private fear
4. What happens when success scales beyond recognition, and the work you love turns into meetings you dread
5. How selling a wildly successful company coincided with a deeper reassessment of marriage, values, and family life
6. The slow, internal process of deciding to divorce, and why midlife clarity often arrives quietly, not dramatically

Andrea’s story is a great reminder that midlife change is not always sparked by crisis or collapse. Sometimes it comes from clarity. As external pressures fall away, what matters most rises to the surface. This episode explores how success can evolve into misalignment, how values become louder in our forties, and how honoring that inner voice can open the door to a more honest, grounded, and fulfilling second adulthood.

If you enjoyed this episode, please take a moment to rate, follow, and share The Big Four Oh Podcast. Your support helps more people realize they are not alone in this transition.

Guest Resources

Connect with Andrea on Instagram

33,000 Dates

Do you have the Midlife Ick?

Download Stephanie’s guide to the Ick to diagnose whether you or someone you love is suffering from this insidious midlife malaise. www.thebigfouroh.com/ick

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The Big Four Oh Podcast is produced and presented by Savoir Faire Marketing/Communications

Stephanie: Hi Andrea. Welcome to the show.

Andrea: Hi. It's nice to see you again.

Stephanie: Oh, it's great to see you too. I love when we first spoke, you said something that resonated so strongly for me. You, you said you were from a big Irish Catholic family and I am as well.

Andrea: I am. I, I am the oldest with six younger siblings. Some of us are not even a year apart. So that's what, like a tight knit. Irish Catholic family looked like and going to Catholic schools all the way from grade school to high school, to even university, I mean, all the way through.

Stephanie: So, I was the oldest and the oldest, you know, it comes with some, responsibility. It, it comes with some advantages too, but it comes with, maybe it made me a little bossier. You know, maybe it helps with leadership skills, I don't know.For sure, for sure. I'm the oldest girl as well, although in my family there were just the three of us, but my dad was one of 10, and my mom, although French Canadian, one of six, so I get the big families. Yeah, yeah. I get the big families. And on both sides there were definitely a. lots of Irish twins, so

Andrea: You know what?

Stephanie: they just I do, I do, I do.

So let's, let's jump in and start at the beginning. Tell me a little bit about who you were when our story of midlife transition begins. How did you become this person who, by all, by all, accounts was really successful and thriving?

Andrea: Oh, thank you for saying that. It didn't and doesn't always feel like that because. You know what I mentioned to you earlier, there were so many, failures along the way. But, you know, I, I learned a lot. I mean, I learned as, as I went because what I ended up doing professionally there's no classes in college on starting a dating thing, you know, or anything like that. So, I, I probably, I go back to when I was like probably 14 or 15, I was an athlete, you know, so I played a lot of sports and, and I was very competitive too. And probably there was, I'm sure that competitive spirit has definitely rubbed off on me, , in the business world too.

And that, and you know what, what it gives you too, it gives you resilience. And it also gives you feelings of, rejection too. You know, when maybe you didn't win that MVP trophy and you're like, I should have. Maybe not, but, those types of things. So, I don't really talk about this very often, but my first friend that I ever fixed up was, we were 14.

14 and you know, did they get married? No. But you know, that, that kind of started it. I was just like, good at, I'd be looking at people and, I would even drive my siblings crazy. We'd go to the movies and I'd be like, why is she with him? She doesn't look like she belongs with him. You know?

So like little weird, quirky things like that. And so, as we progress and it's getting time for college and neither of my parents had gone to college. You know, I grew up very middle class and my mom said, really we should put the boys through college because they're gonna have to support a family and a wife. And honey, you really don't need to go to college. And I was adamant, oh, I'm going, oh, I am going. And I'm finding, some way that I'm going to college. And partially, you know, as loans and a scholarship. And my mom's thought was, no. maybe like take a nice stenography class.

Stephanie: Ah, Andrea,

Andrea: I know.

Andrea: No.

Stephanie: about. This is like the mid to late 80s?

Andrea: Yeah. Yeah. This is, this is the eighties. Right.

Stephanie: Oh my goodness.

Andrea: That's where my, my mom's head was. Now my dad was a businessman. And as I said, you know, I grew up middle class, but really I was one of the three kids that grew up middle class. By the time the younger kids were older, my dad was president of the company, so it was, they lived a whole different lifestyle than I did.

And my dad said, you should go to college. You know what you wanna do. And, I wanted to be a Shakespeare major. And my dad's like, and my, my mom's. Okay, so my mom's finally on board with this college thing and she goes, no, honey, you should be an accounting major because then while your husband's at work and you're having babies, you can be at home and do bookkeeping for other people and make money.

I'm like, oh my gosh, that is not my life. I'm gonna work for one of the big accounting firms. I'm gonna go to Wall Street, I'm gonna go to Wall Street by storm. I'm gonna do this. So, you know that that's what I grew up with. And, though my dad was always, in my court in terms of, both with sports and with, academia and with college.

So he, he was a proponent. And he's, he was a big proponent of women. He was president of a retail chain that was in Cleveland. And, there were so many women, of course that worked in retail, you know, that came managers to buyers, et cetera. So, he knew a lot of women working who had college degrees.

And one thing he did say to me, don't go into retailing. The hours are hell, which is true, the hours are hell.

Try starting your own business. The hours are even more hellish. But you

Stephanie: Right,

Andrea: you love what you're doing.I never thought it was weird to go to work on Sundays and I just have time alone where I could think and I could think strategies and I could, you know, sign checks and, do the thingsI needed to do on my own. As we fast forward, I lived in New York for a while and then moved to Chicago in my early twenties, and I was engaged and I was getting married and a couple days before the wedding he called it off. And yeah. Oh, okay. All of, let's see, Jim, Joanne, and Jacqueline, three of my siblings were already married at this point. So, you

Stephanie: And you're the oldest.

Andrea: Here, here I am the oldest and, you know, at weddings, people will be like, Andrea, you're probably gonna be last after your little brother, Tim. I'm like, I probably will be, but who cares?

So there was so much pressure on that, that marriage thing. So when Mike called off, the wedding, I was devastated. It took some time, probably took a couple months to realize, a door slams shut, you know, a window opens. Right. You know that saying, right.

It's so true. But then I went through the whole thing about,dating. Just dating, and of course Chicago's a good market, to date in when you're young, you're in your twenties. I'm living downtown and my friends would fix me up and I, you know, how do they do it? They do it because they know another single person, right?

That's

Stephanie: Right,

Andrea: And here I am, five foot 10, here's these guys showing up, five, five. nothing wrong with that, but I felt like I felt like an elephant or a giraffe, I felt big. And, so anyway, okay, so.

Stephanie: I, I can, I can relate with all of it. Absolutely. All of it, because I'm also five nine and, not the skinniest girl there ever was. And again, this is back in the nineties when body image was a little bit more rigid, a little bit more, traditional, and so you did, you, you felt kind of like a moose. I'm from the, the northeast, so we've got moose. so Right. You, you felt a little bit like a moose when you're hanging out with with smaller guys and smaller girls. So let's just be, let's just be honest, right. But I also remember, again, I lived in Boston during the same period and, and being single in a big city was a good time.

It was, there was a lot of choice, a lot of options, a lot of, a lot of excitement, a lot of things to do. And I know for me,it was all very, very much distractions from anything deeper. And I think for you, you were much better at getting a little bit deeper with figuring out what a good match was and what made sense.

Andrea: I think so. And yeah, I think there's like something innate in me that just loves, excuse me, fixing people up. So let's hop back to college for a second. My two college roommates, I fixed them both up with their boyfriends, who are still their husbands, and,

Stephanie: Yeah.

Andrea: you know, I, I just liked doing it.

So now, I'm in my twenties and, the wedding's off. I'm, I'm over the tears, you know, and I'm, I'm back in the saddle. And I started thinking to myself, okay, remember there's no Google, there's no online dating. There's no nothing yet. There's nothing.

So I started thinking to myself, wouldn't it be great if like when executive recruiters would call you with jobs. What if they were calling me with dates?

I thought, wouldn't that be great? They're, working on my personal life, they know my background. And so I started thinking about that, and then I had this idea. I thought, wow, if I'm thinking this, other people must want something like this. And so I came up with this idea because I, after a while with dating, I stopped doing dinner dates and and I either went out for a drink on a date or I went out for lunch. And I named my company, It's Just Lunch, and I had $3,000. And I launched the company with $3,000, which I thought it was a lot of money and I thought, you know, oh, I'm gonna be able to, do this. And I am gonna start this thing and I'm gonna take Chicago by storm.

And I wrote a business plan, and again, there weren't business plan books yet. So I borrowed a business plan from one of my friends who started this, restaurant chain called originally Mistake Escape. And then it turned in and then it turned into Brio. And Rick lent me his business plan and I used his business plan to write my business plan.

Then I show it to my brother, a year younger, who's, like an accountant at this point. He looks at my business plan and he goes, no way. These numbers won't work. This is not gonna work. And I had five scenarios in there with my numbers, and I'm like, all I need is 5% of Chicago to join that's single, and you know, I'm a multimillionaire. I was really positive. But I also learned after that, don't show your business plan to anybody else, because everyone thought this was the weirdest idea. And like I.

Stephanie: Well, you were breaking new ground. You were breaking new ground because at that point in time, you're right, no Google, no online dating, no Facebook dating. What there was at that point in time was fix ups. And in the, alternative newspaper in whatever city, there were classified ads.

Andrea: That's right. Village Voice.

Stephanie: That was it.

Andrea: Yep. Those, those types of things. That, that was what was out there.

Stephanie: You were completely breaking new ground, so I can, I can imagine that people would've looked at this and thought, you're nuts, lady!

Andrea: Yeah, exactly. So I spent my entire $3,000 on, first I got this little shared office space and I had enough for like two months rent. And I printed up brochures. I had all these brochures printed up, but then I had no money to mail them. So I'm like, oh, okay. What am I gonna do with the oh, 20,000 brochures.

So it's a Saturday night in Chicago. It's Lincoln Park, which is a big Yuppie area at that time. And I talked to a couple of my girlfriends into, it's like two in the morning. I'm like, we're gonna go deliver these like door to door in Lincoln Park and put 'em on it and they'll get 'em Sunday morning. They'll had a bad date or no date, and they'll be like, my phone's gonna be off the hook. Right.

So, but as I'm walking, we see the Chicago Tribune guy delivering the paper. And he's got like, it's in this nice plastic bag that, I don't know, Macy's or somebody sponsored. And I'm like, oh, we're gonna follow him around and we're gonna stick the brochures in inside the bag and it's gonna look like I'm a real business and I've got money to advertise in the Chicago Tribune.

Right?

Stephanie: I love it.

Andrea: So I.

Stephanie: How scrappy

Andrea: I am back Sunday morning in my office. I've got a bagel. I'm just staring at that phone. I'm waiting, and one of the first people to call me was this woman, and she's like, I think your idea's really unique, and I'm a PR person. I'm like, a what? We all know what PR is now, but you know, back then, like PR and she goes, listen, I'm single too. I'll trade you dates.

You set me up on dates and I will get you press. And I'm like, well, I can't afford advertising. She goes, no, I mean like editorial, like people write about you. So before I knew it, what was starting to happen, like Crane's Chicago Business, a little business publication, did an article. And then Chicago Magazine saw it, which is huge. And they did like a three page spread with, one of the reporters going out on dates and writing about the process. And from there, The Wall Street Journal picked it up and I was like, oh my gosh. Business is like starting to boom now. And then right after that People Magazine picked it up and did like a full page thing. And I was like, oh, this is awesome. And I knew I would do it, you know, I like, when I started it, I was just like, I would totally do this.

And so like, in the meantime, let's go back to my mom. Of course, there's other weddings going on in the family and people are like, what's Andrea doing in Chicago?

And my mom's like, oh, she started this dating thing. And she's like embarrassed, embarrassed, until there's a New York Times article where it said like some of my revenue and stuff, and then she's like, honey, this is awesome what you're doing. You know, this is great. You're helping people. She's probably thinking I'm helping people get married and have babies. Right? That's probably what my mom is thinking. So.I knew I had to get in that New York City market. New York was my second market, and it was a tough nut to crack because people thought, I was like, people don't probably remember this name, like a Heidi Fleiss or like,

Stephanie: executive madam.

Andrea: an escort service or something. So I'm going around to landlords. I'm clutching like my People Magazine and my Wall Street Journal, my articles. Like see, I'm not, I'm not, you know. Finally got office space in New York and boom, the business really, really started, taking off. And I loved it because I loved the contact I had with clients because I was the one still at that point, now I'd hired a couple people, and I was still worried like crazy, like about paying my rent and, how am I gonna do this? And, I mean I was living week to week to week.

Oh, and there's one thing I skipped about, about CNN. CNN was a pretty new network back then. And, I was, standing in a grocery store line. This is still the Chicago days. And there's this girl behind me and she tapped me on the shoulder and she, and we had met at a party the week before, and her name was, I still remember her name, Cheryl Trieger. I don't know her well. She tapped me on the shoulder. She goes, how's that dating thing you started doing? And I was in line worrying about how am I gonna pay my rent next week? That's what I'm thinking. That's all I'm thinking about.

And I go, oh, it's going great. I fixed up Roberta and Jack and I think they're gonna be my first wedding. I think they're gonna get married. She goes, that's great. Couple hours later I get a phone call. This was actually my second piece of PR. She goes, you know, I don't know if you know this, but I'm a, producer at CNN and we'd like to follow a couple out lunch and come talk to you in your office and air it.

Stephanie: That's an example to me of what was I thinking? I'm having these negative thoughts like we all do, like, how am I gonna pay the rent? But I never ever said to anyone, like, I'm scared about anything. But I went to bed every night scared like that first year or two. I was scared. But you know, I put that smile on in the morning and I was like, I'm gonna do it today. I'm gonna, get a couple new members and then I'm enough to pay my rent. Well, and also the, the, those early days of a business and especially one that's growing really fast can be super scary. Because in the beginning it's really built on just momentum and not actually foundation of, oh, I can pay a year's worth of rent at both my locations, right? Because you're, you're using everything that's coming in to, to fill in behind you and underneath you.

And so, so yeah, I, I get that that's scary. Of course we wanna present it positively to the world. So, so that, that all makes, makes a lot of sense to me. But let's jump to, as you're expanding, there was an attorney you brought on board to the company. Tell me a little bit about that.

Andrea: Yes, yes, this was an attorney. Okay. All right. Here. We go with another

Stephanie: I'm setting you up.

Andrea: Yeah. That was a total setup. Okay. So there's this attorney. He's actually a member, right? I interview him in the Chicago office. He becomes a member. He goes out on two dates. Everybody had a call in and give me feedback after the dates.

So the two women, when they called in with feedback about him, said, you know, nice guy, well educated, good looking. But you know, Andrea, he talked about you a lot. And I was like, what? He talked about me a lot. What do you mean? He talked about me a lot and the one woman, I still remember her name, Audrey, she said, I think he likes you.

And I'm like, Ugh. This is in, this is really good for business, right? Like, oh, the owner's dating clients. Like, I don't think so. And I had a policy. Now I have a couple employees. Nobody's allowed to date anyone. His name's Daniel. I call him and I go, Daniel, gimme some feedback on your dates. He gives me some feedback and then he said, do you wanna know what people have told me? And so I give him that same, you know, what just went on. And he goes, well I really came in 'cause I saw that Crane's article and I thought you were really cute and I wanted to go out with you after I met you and the interview.

I'm like, ah, that's really nice. But you know, we have nothing in common and I don't date clients. And so a couple hours later, messengered over from his law firm is his contract voided, and he's said, I'm no longer a client. I don't want a refund. I wanna go on a date with you. I go on a date with him. I marry him three months later. And it lasted for 24 years, so we had a good run. I mean, we're still friends. It was a very amicable, breakup. Okay. So anyway, Daniel, he.

Stephanie: He came on to the business.

Andrea: He, he moved onto the business. He, he was working on his MBA at University of Chicago at that point, and wanted to get in the business world versus law. And plus he, he was doing merger and acquisition work, so he understood, how to talk money and how to talk to private equity and venture capital and bankers, which I had no clue. So he's like, and I agreed, why don't you come on board because I need some more money to be able to expand this rapidly because what was happening at this point are starting to get knockoffs. So at this point I had, Washington, DC and Dallas, Texas too. And people were starting to do It's Only Lunch or Just For Lunch or just, knockoffs of my business. And so, he was able to procure the money, to give me a little bit of a runway, to give us a little bit of a runway.

And I was able to buy out these, knockoffs, which was good 'cause it gave me, a foothold, in, in the market, like Atlanta, and, Orange County and San Diego. So anyway, he was a, a great addition, to the company. We, and we worked on such different things. I was very, client based, working with the clients, making sure the clients were happy, making sure the clients are meeting people and he handled like the backend stuff.

So, it was a really good run working with him, I will say, I will say that so.

Stephanie: That, that really sets us up. So that gets us through your mid to late twenties, and you've got this business that is just, like a nuclear mushroom cloud blowing up across the country, becomes this enormous and successful endeavor. So let's flash forward like 20 ish years. Now you're in your mid forties. You have three kids, you and Daniel are running this enormously successful nationwide dating company.

Let's talk a little bit about how things start to shift for you and whether it's shift or clouds clear and you start seeing things differently. I'm not sure which version of that you'd describe it as, but, but things started to shift.

Andrea: Yeah, things definitely started to shift because now we have 110 locations internationally. I don't talk to clients ever. You know, I've got seven, or 800 employees. I miss that part. Plus I have to go to board meetings now. I have to go to a lot of meetings and I am like, this is so boring. This is not what I wanna do. Like, I miss, I miss the people part. Like I'm a people person. I like helping people. And so what happened, it was just all really like serendipity. A couple things happened.

Online dating, which had been a mess in the, when it started in the late nineties and the early two thousands. It's chaotic. They're all trying to find their business model. People aren't who they say they are. They're scammers out there. So we're now past that point. Online dating's looking like, Hmm, this could be the wave of the future. They're getting their act together. Or a lot of the sites and apps are getting their act together.

And at the same time, I wanna spend more time with kids and I wanna take some time off. And two people approach us in the same week. One is match.com and one's a private equity company and say, interested in selling your company? I was like, yep, I am. I don't wanna go to another board meeting.

We ended up selling to private equity and I, at first they were like, we want you to stay on the board. And I'm like, no thank you. I don't wanna go to any more of these meetings. And so I got like two years of just being able to travel all over the world with kids. And just do things. And you know, now they're in school and stuff and they don't need me quite, quite as much. And so I'm starting to think more and more, okay, I miss it, but I miss the people part. I, I don't want, It's Just Lunch back. I wanna do something different. And it really all started with my brother. Now this is my brother who said the business wouldn't work, and I'm super close to him. And we're Irish twins.

Okay. Jim gets divorced, he goes online and he's having horrible dates. And he calls me and he goes, online dating is awful. And I'm like, Hmm. What are you doing? And he goes, I don't know. I'm getting horrible dates. And so I'm like, give me your login and your password and let me see what you're doing. So I go in and at this point he's a CFO of a company. So he's successful and good looking guy. Okay. I go in, I look at his stuff on the back end, I'm like, oh, you're such an idiot. Uh, that's okay. He would never listen to this podcast. Okay. so,

Stephanie: Sorry, Jim.

Andrea: So, and he's a bright guy, right?

Stephanie: I've got her all riled up, so it's my fault. Okay.

Andrea: You got the honest story. In my book, I use another person. I don't use my brother, but in real life it, it is my brother. So I fix his pictures, I fix his bio. Couple weeks later, he is like, wow, I'm meeting really good quality women. And I'm like, you can just say, thanks, Andrea. I changed a bunch of stuff. And from there this started rollingmy next phase, which is 33,000 Dates. Because at that point in time I had set up over 33,000 dates thus far in my career. And he started referring me people and then people heard about it, word of mouth, and next thing I know, I'm a consultant.

Stephanie: You know, this is not the 1940s. We are fifties or sixties. We can approach men. And so, I started teaching about how to write messages. I would even write their messages for the first couple of coaching calls for them. And then this turned into a big business. And that makes a lot of sense to me because it goes back to what you loved about the beginning of the first business, which was just the people to people contact and the drawing out of, what's special about different people and helping them clarify what it is they're looking for. It's, it, it makes total sense to me why, why this would be a, a great, and very,very well aligned second act for you.

But I wanna circle back. What I really wanna dig into is your midlife transition, which part of it was selling your company, but there was also transition in your personal life as well. You went through a divorce. So, so let's go back again to that, that mid forties and talk about how things started changing in your life, in your personal life as opposed to your business life so much. I wanna hear about how things were shifting inside of you, in your head, in your heart, in your gut. Talk a little bit about that.

Andrea: Well, you know, I think so much of my marriage was wrapped up in we were growing a business together. And I, I used to read the New York Times stats and it was something like 90% of people who worked together, couples, they end up getting divorced and all of a sudden there was this chasm, like there was this big like, wow. We were great business partners, could probably still be great business partners, but it just wasn't working.

One of the issues too that I started to see very, very clearly, we had very different ideas on children, how to raise our children.Religion came into play. I mean, not that I'm like fanatically religious or anything, but like, there were so many factors that I didn't see when, what did they say, you're in the weeds, right? When you're, you know, running a business together. But I started to see it and it started to see kind of the impact it was having, on the kids with two parents that didn't really agree on a lot of things for kids.

My ex-husband was very much a pushing, he had an Ivy League education, Ivy League was what it was all about. I was about, I wanted them to have a solid family life. I wanted them to have a great social life. I wanted them to be happy and healthy and, not push so hard. I mean, I, I was never really pushed that hard either. We wanted two very different lifestyles.

I would go to yoga, and I'd lay on my mat and it would be during Shavasana, you know, at the end of yoga. And I'd lay there and I'd think, get divorced, don't get divorced, get divorced, don't get divorced. This went on for like a year in my head. Like, get divorced, don't get divorced. It's gonna be really disruptive, but you know what? It's not working. So, you know, all these things were going through my head and I finally said, I want a divorce. This isn't working for me. Our values don't align.

And, that, that's one thing I always say to clients too, that,you gotta have chemistry, you have to have good communication and you have to have common values. And just a few weeks ago I was in Boulder. My youngest daughter's there in college, and I took her and like five of her friends, out to dinner, and one of 'em was asking me about dating. And I, I said those three things again, you have to have those three things. And my daughter looked at me and she goes, did you and dad have any of those? And, and, and, and we all start laughing because here's a kid, recognizing that, seeing, you know, and I didn't know they saw that much, but they do.

Stephanie: And it's interesting too because when we're in our twenties, there are things that are important to us. And I've, I think I've said this before. I have aA dear, dear cousin who, when she graduated college, we're about the same age, when she graduated college, she started dating a guy and a couple of years later they got married. And, and at the, at the time, the big selling point for him was that he was cute. He was cute and he was fun to be around.He was an extrovert, she was an introvert. He pulled her out of her shell and they did really fun things. But, 20 something years later with, with a couple of kids, there are different things that are important. And they've been very fortunate to grow together. Um,

Andrea: I was just gonna ask you that. They grew together, so that that's the big difference. Yeah.

Stephanie: Yeah, they, but, but that's what happens, right? You, you have certain things that are important in your life, in your twenties. Certain things that are important in your life, in your thirties. And then in this, in this transitional period that we go through sometime around age 40, plus or minus, we start to realize what's important to us personally versus what's important to get ahead in my career, what's important to, get us the right house or the right neighborhood, or. The things that are important to you start to shift and change.

Andrea: And that's that midlife thing. And that's when a lot of people go through midlife crisises too. Right. So, maybe that was mine. Mine wasn't because there was another man involved or anything. Mine was just, that the impact on, you know, the people close to me that I, that I saw and.

Stephanie: Well, and it, it makes sense too because this was about the same time that you sold the business and so, as you're thinking about extracting yourself from this business, which I have to assume was all consuming for the 20 years before you sold it, you're starting to see your partner differently. You're starting to see your partner not as, 95% business and 5% home, personal, kids, life. And, and now that home, personal, kids, life component is getting bigger and the things you're seeing aren't feeling so good to you.

Andrea: Exactly. Exactly, and, and there's still so much life to live. When you think about, do I wanna be thinking the same thought for another 30 years? No. I mean, it, it took me almost two years to come to that decision, like divorce. You know, it, took me a while.

Stephanie: Let me go back to the very beginning of our conversation where you said, he's a wonderful man. You had a great marriage. You built a great business. You had an amicable divorce. None of this points and says, there's no pointing fingers that says, you're a bad person. This is terrible. I wish I never did this. It's just that what was important to you was shifting.

Andrea: Right, right. And you know, I think, I think it probably always was important to me. But maybe, well, you know what? Maybe not. Maybe because I got so, so much of a push from my mom about the whole, like, marriage and kids and, that's what life is all about. Procreation, you know? I'm

Stephanie: Right.

Andrea: Whoa. I mean, maybe, maybe that's why I was, it took me a little longer to come to, to come to this realization.

Stephanie: it doesn't surprise me at all because you had a fourth child and your fourth child was this business, which was so huge in your life. That, that I don't know, maybe it's just 'cause I'm looking from the cheap seats and maybe it's 'cause I, I have these kinds of conversations quite often, but I think it's, it's easy to see that, yes, those things were always important to you. And your kids were younger, and so that push for the Ivy League might not have been as strong when they were four and five and seven and eight, right? Until they're 12 and 13 and 15 and 18. And it's, it's a little bit more, intense.

But also you've got this huge business that is, that is part of your life. And as that starts to sunset, there's more room for some of these other thoughts to come through, and for you to see a, a bigger picture for the family life to take up more room in your view.

Right. And not that it wasn't important. I'm not trying to diminish that, but I'm just saying if you look through a windshield, right, you can only see so much in the windshield. And if there's a mountain, if there's a mountain you're, you're driving towards then, then what you can see aside from the mountain is only part of the windshield. But as you come around and the mountain fades, you can see more sky. I think that's what I'm trying to get at. Does any of that feel like it fits a little?

Andrea: Yeah, I, I think that does, I think that does fit. And, something we never talked about before that I'm gonna add in that I've never talked about in a podcast, is, a couple of years after we sold the business, I had cancer, so I went through like a year of all of that stuff. And, and that really makes you think about what's really important too, because how many more years do you have? What's it gonna look like?

And, I mean, knock on wood, wherever it is, it all turned out well, but, you know, all those things,shape your decision making and

Stephanie: Clarify your priorities.

Andrea: And then, again, it all turned out really well. Three years ago when I met an amazing man, online and, that's a whole nother story.

Stephanie: Well, and what I love about that part of the story is that, in, in this one, again, I can relate to Boston Irish Catholic big family, right? The like, that, that actually is my, my dad's family is from South Boston. And it, it makes sense, right? The, the fit there. There's a lot of, a lot of, common values, a lot of common background, common foundation, when you're coming from that big Irish Catholic family.

Andrea: Exactly, exactly. It was, it was just, it was such a change. And,right away we clicked. And when, when I jumped into online dating, and I think I told you this a while ago, my first week I went on five first dates with different people and you know, it was fun and everything and everyone was normal and nice, no chemistry.

And then about two months later, I met Jeff and like I knew, like halfway through that lunch, I was like, this guy's golden. Like, I really like this guy. And we, like you said, com, common backgrounds, common values, and, and I do believe the common value and, and of course you gotta have chemistry too, or you're just gonna be friends. And, he was easy to communicate with and,you know, worked.

Stephanie: Yeah. Yeah. and fits for this part of your life where you are really all about you, and what's important to you, and what's fulfilling to you, and, and what's aligned with you, and not so much the external factors of raising a family, building a business, all these other things, right?

This is, this is a much more, I don't, I don't understand why I can say this is a much more personal choice, but, 'cause they're, they're all your personal choices, but the others had so many other factors in them.

Andrea: Right, exactly.

Stephanie: And this is stripped back to just Andrea.

Andrea: Right. And and this is what, this is exactly like what my clients are going through, 'cause it's second acts. We might not get it right in the first act. Or the first act might have just been taken away from us because our partner died, or something like that.

But,a second act, second marriages, I mean, the, the, the statistics are so strong on both people who get married later in life and second act marriages, or second act relationships. And my clients, like my clients that are in their forties and fifties, a lot of them tend toget married, where my clients that are in their sixties, they're looking for that long-term partner. That's what they want. They want the long-term partner and they really don't care about marriage and, and none of these people at this age in the second act care about kids. So we've taken that whole thing off the table where everyone's clocks were ticking when I was at It's Just Lunch with the twenties and 30 year olds, where at 33,000 dates that it's not like that anymore.

Stephanie: Yeah. Again, it's just an illustration of the different priorities at different stages of our life, right? When we're young, we're thinking about kids. And then when you have kids, there is 20 years where you are focused just on the kids, right. On, on getting them, grown and launched. And so, once that variable is off the table, there's a whole different math to what it is that you want and that works.

Andrea: Right. And I just had a woman call me the other the other day, and she's 70. She said, am I too old? And I said, are you kidding me? No, you're not too old. I mean, my father-in-law just passed away a couple months ago and he was 97, and up until the last few months of his life, he lived this great life. It's not like our grandparents era. We've still got a lot of life in us. So it, it, it's, it's very common for people to be seeking this out, in their fifties and sixties and even, seventies.

Stephanie: Yeah. That is true. Oh, Andrea, thank you so much for joining me today and, and for being so generous with your story. I've, really enjoyed hearing about your midlife transition and about, your whole journey.

Andrea: Oh, thank you. Yeah. For some reason you got more out of me than most people do. I don't know how you did that.

Stephanie: It's my magical mystical powers.

Andrea: Yep, yep. That's called a good interviewer.

Stephanie: Oh, thank you so much. I appreciate your kind words.