How to Date in Midlife with Confidence with Kerstin Rao
How to Date in Midlife with Confidence with Kerstin Rao
Kerstin hit a few crossroads at midlife - a divorce, becoming an 'empty nester', and leaving her 34-year teaching career to start two businesses. Three essentials that helped her grow are life-long curiosity, a sense of humor, and reaching out to guiding-light people. Today she uplifts others through her art business, Vivid Cottage, and her dating mindset coaching service, Curate Your Mate. Follow on Linkedin or Instagram.
Dating in midlife can feel like a minefield—swiping, bad dates, and wondering if you’ll ever meet the right person. But what if there was a better way?
In this episode, I sit down with Kerstin Rao, a midlife dating coach who went from disaster dates to finding her perfect partner by building a dating system that actually works. She shares her most outrageous dating fails (yes, there was a convicted felon), but more importantly, she explains how to date with confidence, clarity, and strategy—without wasting time on the wrong people.
Key Takeaways from This Episode:
✔ Why random dating leads to random results (and how to fix it)
✔ The biggest mistakes midlife daters make—and how to avoid them
✔ How to get crystal clear on what you actually want in a partner
✔ Why dating multiple people at once can help you make better decisions
✔ How treating dating like a career search can get you better results
Your Midlife Dating Strategy:
1️⃣ Reflect on your past – What patterns do you keep repeating?
2️⃣ Get specific – Write down the exact qualities and values you want in a partner.
3️⃣Date with intention – Approach dating like a serious search, not just wishful thinking.
4️⃣Stay the decider – You’re choosing them, not the other way around.
Midlife dating doesn’t have to be exhausting—with the right mindset and system, it can actually be fun.
If you enjoyed this, you might also enjoy my Life Satisfaction Assessment. It's a 30-minute program where I guide you through a deep dive into 10 areas of your life to assess what's bringing you joy and what's bringing you down. I call it Derailed and it's a fabulous place to begin a joy-at-work redesign.
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How to Date in Midlife with Confidence with Kerstin Rao
[00:00:00]
[00:00:00] Introduction: The Messy World of Midlife Dating
Lucia Knight: My guest today, Kerstin Rao, is a midlife career changer. She walked joyfully away from a successful teaching career and created not one, but two businesses. One that showcases her fine art talents and the other as a mindset dating coach for midlifers. Today she shares some of her own hilarious midlife dating disasters, which then encouraged her to create a dating [00:00:30] system that worked better.
This resulted in her investing quality time and energy into successfully finding her long term partner who is just right for her. Kerstin shares some hints on how she did that. And if you're watching this on YouTube, I apologize for my facial expressions. Let's dive in.
Kerstin, over the years, you have shared some [00:01:00] dating disasters with me, but those dating disasters also led to you creating your own method and to successfully discovering your husband. Please, can you share some of your dating disasters?
[00:01:12] Hilarious Dating Disasters (Yes, There Was a Bank Robber)
Kerstin Rao: I love sharing these kinds of stories as long as there's always hope at the end. I find that people can feast on each other's dating disaster stories to the point where they talk themselves out of getting back out there. So that is my little caveat before I tell you just a few of my [00:01:30] funny stories. Because I'm obviously a person who always wants to land on hope.
So I was single in my forties, mid forties, and I thought, Oh, good Lord, what's this? And how do I put myself out there? I have no idea. So I just jumped in the pond, which is something I do.
I am a leap before I look kind of person sometimes, especially when it came to romance. I had no playbook. So I jumped out there [00:02:00] and I wound up dating a bank robber. Yeah, convicted felon. So just a couple of dates and it was a shame because he was cute and talented and a good photographer.
But he said, I have a policy on my second date. I tell, whoever I'm dating the second date, I tell them my story. And I said, I'm a School teacher, what do you think the parents in my small town are gonna say? Like, [00:02:30] Oh, she chose a convicted felon. That's cool. Let's send my kids into that classroom. I'm like, oh. Oh it, it, it was rough. Then I'm dating round and I meet this guy and he seems very clever, very artistic, a lot of fun.
And he gives me a CD of his music. And before I go home to listen to the CD, he said, I wrote Greensleeves. And I said, my understanding is Greensleeves is a hundreds of years old. He said, [00:03:00] yeah, that was me.
Lucia Knight: What? In a past life?
Kerstin Rao: Multiple past lives, which listen, I am not going to yuck anybody's yum because sometimes people discover and unlock things about themselves.
It just is not what I was looking for in a life partner. So I had to just step away from that one. So that, yeah, that's, and then, oh dear Lord, this is the third [00:03:30] and craziest one. So I, connect with some guy. He says, I'm going to drive out and we're going to go for a walk on the beach. I was like, great. He drives up.
He's like, how do you like my Ferrari? This is, he calls it a Ferrari. Maybe it was a Ferrari 35 years ago. Put it in rust. You open it up, you can see the road through the floor. I did not get in the car. Pro tip, never get in a car with some guy you've just met. So we're walking on the beach and the guy says, [00:04:00] I've already planned our threesome.
And I said, WHAT? There was nothing in our exchange of information. I'm looking for a life partner. Not that. So bye.
Lucia Knight: Okay. Oh my God. Brilliant. So I can see why you looked for a different way. So tell me, I really want to know, so you in [00:04:30] your role as founder of Curate Your Mate, you help clients deal with this messiness of dating in midlife. Tell me a little bit more about how you support clients who wish to find a long term partner.
Okay.
[00:04:48] How Kerstin Built a Dating System That Worked
Kerstin Rao: Absolutely. By the time clients find me either they have been through some, you know, challenging seperation from a partner and they're finding themselves in very uncertain territory. And some of them have had dates, not unlike my experience where they go out there and they are just so mismatched in the dates and they just kind of want to give [00:05:00] up.
And they'll hear that I'm a dating mindset coach and suddenly they'll say what's that?
[00:05:15] Step 1: Get Clear on What You’re Actually Looking For
Kerstin Rao: And the first thing that we do is what I actually did after that series of just disastrous mismatched dates. I took a beat and I got still, and I asked myself, [00:05:30] How did I get to this point in my life? What are the things that I'm vulnerable to?
What were some moves that I made that were not self affirming moves? You gotta get honest with yourself about your history. Because history will repeat. Unless you've analyzed it, look at it, feel it, deal with it, and then set up systems to protect yourself from yourself. [00:06:00] So that's actually what I did. I thought, Kerstin, this random approach isn't working.
The next step after looking at my history was, what am I looking for? Let's be real. Let's say you go to a restaurant and you say, I am hungry. I want food, please. What's gonna show up on your table? God knows!
Lucia Knight: Yeah.
Kerstin Rao: But if you go in and you sit down and say, I would like a bacon, lettuce, and tomato sandwich with rye toast, toasted lightly, [00:06:30] light mayonnaise, and then cut diagonally, you are much more likely to get what you're, what's going to satisfy you.
So taking the time to get super specific about the core values that you are looking for in a life partner, the attributes, the activities you want to do together. And really sit down alone and quiet, not on a dating app, not just a casual chat with a friend. But [00:07:00] take a few days to really write it out.
Until you look at that list and you say, Oh, when I find this person. We're gonna click, we're gonna have so much fun, my life will be elevated, his life will be elevated.
Those are the steps that we take, and then I help them craft a profile that's really gonna put themselves forward, and yet in a delicious way.
Lucia Knight: A delicious way. That sounds intriguing. Any hints for actually [00:07:30] going on the first date, physical date, that you've, you maybe haven't been on a date for a decade or two decades? Any advice?
[00:07:40] Step 2: How to Approach First Dates with Confidence
Kerstin Rao: Oh god, I'm feeling butterflies just remembering what that was like. Um, Yeah like, go out and remember that you're the decider. I think that's the important thing. I'm going to give you some stats before we get there. [00:08:00] I was single from the signing of my divorce papers to meeting my amazing partner.
I actively dated for an 18 month period. And when I say actively, I treated it like a full time second job. I had spreadsheets, I took notes after the dates. Let me tell you something. I put in the hours and the time. Took it very seriously because for me, I was looking for something serious. A lot of people that I've met and [00:08:30] coached have kind of an arm's length. I'm maybe dating. And I'm like, then you're going to get maybe results.
Lucia Knight: Brilliant.
Kerstin Rao: So
Lucia Knight: all in?
Kerstin Rao: it all in, have your little plan for the traps that you know, like I built in systems. I was like what do you do if you make too much out of the thing? Do a lot of research, like talk to a lot of people.
Ask them about their dating, watch some TED talks, just get into the whole thing.
[00:08:56] Step 3: Why Treating Dating Like a Career Can Get You Better Results
Kerstin Rao: treat it like, really treat it like a career because [00:09:00] it's that important. It is that important but I realized I should probably be not dating just one person at a time. One person, I fixate and I try to make it work no matter what.
Multiple people, suddenly, it's more like Consumer Reports I'm the shopper and I'm like what does this cost versus what does this cost? How many calories does this have and does this have like almond flour or whatever?
Lucia Knight: So you can be more analytical if you're dating a few people at the same time. Okay.
Kerstin Rao: reminded me that [00:09:30] I'm The decision maker. I can take my time. This is an important life decision. And it just re centered me into myself. And what was really going to light me up.
[00:09:44] The Payoff: Finding the Right Partner
Kerstin Rao: And when I finally did meet the right guy I can't even tell you. It has been the best relationship for me at this point in my life that I can possibly imagine.
And that's why I do what I do. [00:10:00] I want other women to keep the faith in themselves. Keep getting out there because by putting yourself out there with a system in place, you're really increasing your chances of being so happy.
Lucia Knight: If you enjoyed this, you might also enjoy my Life Satisfaction Assessment. It's a 30 minute program where I guide you through a deep dive into 10 areas of your life to assess what's bringing you joy [00:10:30] and what's bringing you down. I call it Derailed. It's a fabulous place to begin a joy at work redesign.
