the INTERWOVXN podcast
Interwovxn’s co-founder Theresa talks with matchmaker and middle age dating specialist, Lori Mendelsohn of Smart Funny Single, about dating in middle life, changing dating paradigms, letting go of expectations, what makes a great first date, and more. Listeners hear Lori talk about how she arrived at her current profession, and share how her professional skills are rooted in real life experience. Theresa and Lori get right into nitty-gritty topics like dating after divorce, sex after menopause, getting out of a dating rut, and embracing change.
Connect to Lori + Her Work:
www.smartfunnysingle.com
Instagram: @smartfunnysingle
Facebook: https://www.facebook.com/smartfunnysingle/
Episode TRANSCRIPT
THERESA: Hi Lori, thanks for being here.
LORI: I'm thrilled to be here. Thank you.
THERESA: I'm dying to know, like a little background about how you got started in all of this. I know that you are a student of human nature. Can you talk about the moments you realized that this was your calling?
LORI: My back story is not as a dating coach and a matchmaker. Although I started doing matchmaking when I was 19 years old, it was when I was in college. And I had just met a guy, and I intuitively said, oh, you two should meet and then they ended up getting married and then it kept happening over and over and over and over again, resulting in marriages and now great grandkids. Because you know that was 40 years ago. You know, I'm 66 years old, so I've been doing it a while, interestingly enough. I met a medium a few weeks ago and he knew literally nothing about me and he looked at me and the first thing that he said was when did you know that you had this gift of connecting people? And I said I've always known it. I just was afraid to use it. Because I was a misfit kid. I was empathic. I was very much a loner. I was. I was that odd girl that no one ever chose for teams or sports. Because, you know, I don't have an athletic bone in my body, but I knew that I had a gift and I knew that the gifts that I had one day I kept telling myself you're going to use those and you're going to be helping people. In fact, one of my clients yesterday when I was doing a coaching session with her she said to me, have you been a psychologist before and I said well she said this is just so easy for you and it absolutely is easy for me. It's easy for me to see the challenges that women are having. And how women get in their own way. And I feel that I am that culvert to them. Seeing what it is that's blocking them and helping them release it, you know they have a lot of aha moments to quote Oprah. They have a lot of moments that they're swearing and saying holy blank. How did you know that about me? And I just know I see intuitively things that people don't normally see and the gifts are hard to explain.
THERESA: In that vein, I wanted to ask, how did you make peace with the empath in you. It makes childhood a little challenging when you feel things so deeply and don't have the language to explain why. How did you move through that?
Lori
I struggled with it. In all fairness, I struggled until about my mid to late 50s. I went through a lot of therapy and my therapist said to me, why don't you change your perspective? Realize that you're not going to be everyone's cup of tea, and that's OK, and you don't need to be. You don't need to be that popular girl you know which is something that I struggled with. You know, of course, when you're growing up. You want to be the most popular girl. I think what I did was I put my efforts into my career because I was odd. I knew that I had design talent. I was a fashion designer for 33 years. A good part of that being in New York. And also all over the country I had my own. Brand that I sold the Saks 5th Ave and Neiman Marcus and all these high end stores and I just embraced this talent. This design talent that I had but it wasn't until my early 60s that I really let out this calling because of self acceptance. It would be going against my own grain and my own beliefs in myself. If I tried to block it down and if I tried to conform it because life is just a lot easier living in the space of who I really AM.
THERESA: Isn't that one of the gifts of middle life, is that we start to realize that our true joy comes from being centered within ourselves with our own set of unique gifts that we came into this world with and finding ways to live in that.
LORI: Without question, when you just realize this is who I am, this is what I'm meant to do. I'm not going to fight it anymore because fighting puts me in a headspace that I hate, I mean I worked in corporations where I would just question every single policy that they had. To the point that they'd fire me. When you just release and accept. This is who I am. It's just such a more peaceful, gratifying and beautiful life that we create for ourselves.
THERESA: Wish we could bring that to our young girls to help shift that prioritization in childhood. But what a gift to bring that to dating in middle life. Finding connection, the best connections, you really have to start with your connection to yourself.
LORI: You can come into it and you can be in that space of uncomfortable. I know who I am. I know what I bring. I know the quality of the person who I am. I know that I have the emotional availability. You know, a lot of women are challenged by finding that but women are also challenged by a myriad of other narratives.
THERESA: On that note, what are you addressing and talking about with your clients when you're getting started?
LORI: Let me give a little bit of background how I got to this space of being a dating coach, so I was divorced at 60 years old and really never thought that I would be in that place. It was a defining moment for me because I was afraid. I was terrified. Actually I had this whole story in my head that I'll never meet someone. I started doing online dating and I started meeting a lot of men and I started making a lot of mistakes in that whole process and I realized that I needed to teach what I learned, and what I did right and what I did wrong, to women in our age group. Because what I repeatedly hear is, here it comes: There are no good men out there. Now we know that that is not true. And we also know that our words have power, and we also know that when we put that out, that is what becomes, and that is what happens. So I lived in that space that there are no good men out there that they're cheater, cheater pumpkin eaters. And they're, you know, they're slight devils and they're catfishers and they're every label in the book in the dating world. But I realize there are also some really, really good ones. They weren't really good for me, but there were some really nice men out there and I felt that it was my duty to teach women how to sieve through these dating apps. Apps I learned how to write profiles from a male POV, so a man would be interested in starting a conversation. I started doing matchmaking after I sold my business, then COVID happened and no one could go out on a date. So I pretty much just shut down and I realized I have to teach this to women now, but most importantly, rather than just dating, how to find out who they are, what their patterns are, what their blocks are, what their barriers are, what the cycle is that they keep doing over and over again, and that's the work that I do. The work is that. That I go back into a woman's youth. Her whole dating narrative. What she learned, what she thought she was supposed to do. Because we have these stories that we were told, especially in women who are in their 60s, that we need to find men who are professional that make X amount of money that drive ex cars who have ex homes. And it's just a lot of hooey, is what it is at the end of the day, that isn't the man that any of us really wants. We want a man who is good, kind, supportive, and who shows up. For us it was there when we're sick as we go into older years, 70s and 80s, it's gonna be there when we go through illness. We don't wanna go through this again. That's the work that I do.
THERESA: Really meaningful, and especially as we are getting to know ourselves in a different way through middle life and then thinking about the coming decades. It's very different. Was this like a pandemic pivot for you?
LORI: Yes it was. Because I had clients lined up for matchmaking. Ready to go and then I couldn't do it. And I thought, OK, you know I have to do something to support myself to be who I am, which is to provide service. I help others, I encourage others. I lift others up. It gives me the same amount of joy to help others as it does for me to fall in love with someone or be in a relationship, you know what's going on right now is I have never been busier. I am having record record months and you know Full disclosure. I moved to Maine and there's a story to why I've moved to Maine, but I moved to Maine and I have never had more Milwaukee clients and I'm thinking, Gosh, if I had stayed in Racine, which is where I used to live, I wonder if that would have happened. But to get really woo I had this thing called an astrocartography. See chart done and it told me that this sweet spot for me to be in is in the Portland, ME area and there's a swath of 45 miles east and West and North and South, and that's where I'm living right now. I'm making new connections. I met someone great. It's all happening because of the energy shift for me. This is where I'm supposed to be, but the cool thing is, is that I am attracting all of these Milwaukee women and the majority of my business still is people from Wisconsin.
THERESA: When you feel that energetic shift you've jumped in the river and now you flow. Let's dig in a little bit to the dating life in middle life. What are some of the differences about dating in middle life? I know we just touched on a few points before.
LORI: The difference that I see is that while people still want well, I'll start with the sexual portion of it because I think in our Twenties, 30s and 40s, the majority of people, that is their priority. They have to have chemistry. You know we're at a time in our lives at those ages where we're procreating and nature truly is taking over, but as we go through menopause and men go through “manopause”, you know I call it companionship. At this point, shared interest, shared experiences, shared goals is more the imperative. Now it's the icing on the cake to have an amazing sexual relationship. As we age, our body changes.
THERESA: There should be something we're talking about because our bodies are no longer biologically wired for fertility goals.
LORI: With that being said, yes you know when we go. And a pause our desire changes. Our bodies are unable to have sex as long as we used to, and the beautiful thing about that is that that also happens to men, so it becomes more of, I'm not gonna say an acceptance, it's an understanding that as we age, the things that are truly more important are the quality of a human being. What this person adds to your life and how they contribute and vice versa how you add and contribute to their life and the kindness and the humility and the conversation becomes more important. And the shared interests and the goals become more important rather than procreation. And having banging kitchen table sex is what I call it. Our bodies change and our body shape changes and it's that also that acceptance, which is something I struggle with. It's that acceptance of wow. I don't have that really tiny waistline anymore.
THERESA: We have to come to terms with our body no longer doing things it used to and now doing things that it never did before. That is a mental and emotional adjustment for us.
LORI: Without question and and we now discuss ailments you know. I've asked men this, I said, did you imagine that we would ever be having these conversations in our 20s that we would be talking about our list of medication? Or having a senior discount. But I think that as we age, we shift into a mindset of forgiveness, of wanting to help others and to be far more compassionate. And that is, that's the sweet spot of finding a partner who is in that same space that you're in.
THERESA: That's beautiful, and then I think it makes a lot of us exhale. I did get a question about what if you never dated before? So what if you married young without really dating around much, and that relationship ended? However, it ended yeah, and now in middle life you're trying to get back out there and make a connection.
LORI: What I would do is, and this is something that I advise my clients is to go into dating without any expectation which is very hard because you know there is a Disney-esque theory and you know that we were taught as little girls that this Prince comes along and takes care of us and all of our problems are solved, and very few of us ever experienced that. The Prince creates a lot of problems.
We need to go into it as I am meeting a new person. Full stop. I'm meeting a new person I wanna see I wanna learn about this man or woman. I wanna learn about this person. Get to know them. Be curious about who they are, what they love to do, what they're about mentally, physically. And not have this expectation that it will end in something we project an ending you know, and we were taught. The ending is when we were younger. The ending is we're married, we're getting married. We're having kids. That's our ending and hopefully we have a happy life together now. I really advise women to just live in the moment and enjoy the company of a man or a woman. And see how you feel. See what their energy is like. See how you feel. Assess when you are with that person what this person brings out in you. Do they make you feel safe or do they trigger you and vice versa. You know we don't have to make these decisions anymore. A lot of people will say, well you know, I'm in my 60s, I'm, you know I'm running out of time. The runway is shorter. Yes, the runway is shorter. You could also get hit by a bus at 40. You know we don't really know how long our life is going to be if we go into it with an open mind and a curiosity that I just wanna discover what this person is like without pretense without expectation. Without an end game in mind, just go with it and that's the beginning and end of it in terms of how to date. Be yourself, you know. I mean, you should show up. You should shower, you should have good hygiene, but you should be yourself. You should wear things that make you feel either comfortable or sexy, or a combination of both. You should wear things that make you feel good and you should have conversations that challenge someone else in that illicit conversation. That's dating and dating is, in my opinion, it's a series of these. Meetings to see compatibility and see if you want to go to the next date. You know you don't have to say, well, it's been 5 days we should be, you know, in a relationship already. Now I have to be on five dates and see if you enjoy that person's company, and then if you want a sixth date then you go on a sixth date. That simple.
THERESA: How do you help your clients avoid or work through the scarcity mindset? I better take this person because there might not be much better out there.
LORI: You know there was something that you mentioned. Earlier, which is that in order to be in a relationship you need to 1st be in a relationship with yourself. If you're not at the point of being in a relationship with yourself. That's the first step. That we need to work that part out and figure out why you are not in a relationship with yourself, why you are constantly looking for the gratitude and the connection with another person you know also known as semi codependence. If you are happy and content with your life you will not make the mistake of latching on to someone just to fill that void. You know that void can be the size of the Grand Canyon if you are in a place where God I've got to be with someone or else I'm worthless or there are plenty of wonderful people out there, men, women. Every shape, size, color. The biggest mistake that I see is that people have this idea. Of what he or she needs to look like and be like. There's plenty out there. There are plenty of great people out there. We just need to be more open to the outside packaging. I mean, I'm going to give you an example. If I may. OK, so last week my stuff was packed and hauled off in a storage facility and he moved it. He moved it out here to Maine, Heck of a nice guy. He's 61 years old. He wasn't George Clooney. I'll leave it at that, but he told me, he said I just can't get a date and he said I'm fun, I'm outgoing I'm well traveled, I'm curious I'm you know. He had a lot of really good qualities. He's a good listener. He was fun. He was funny and kind, he said. I just don't really understand it and I told him. I said the problem is, is that most women are educated. He had a building. Company prior to being a long distance mover. The problem that I saw was that women have the education that the only acceptable man is a man who has an undergrad degree. And all of the accoutrements that go along with it. Here was this wonderful kind man. He's a mover, he's a cross country mover. The great thing is he's self-employed. He can stop it, you know, wherever he wants an explorer. But yeah, he also had built a really successful building company and he had even built his own ski lodge where it could house 50 people. I mean, that's pretty impressive. He didn't fit the mold of what we think we need to be with. That's the biggest thing really. We just have this mold. This idea I mean.
THERESA: I mean that goes back to what we were talking about when we first started talking here. Is that programming and those messages that we were sent when we were young. What's important? What do we prioritize in another person?
LORI: Also, to get family acceptance, you know that's another one you know, friend accept. When's family acceptance? You know? Well, why aren't you dating someone who is XY&Z? I always say turn it back to them and ask them why is that important to you? I want to be in a happy relationship. I met someone who is a builder. He's not an executive. Explain to me, help me understand why that matters.
THERESA: So then when you are helping your client create an online dating profile, can you reveal some of your fundamental tips?
LORI: The fundamental tip that I can give everyone is do not write down what you don't want. Because a lot of women write a list. Of what you must be. You must be this. You must be that. You must be at least this height. You must make at least this amount of money. Going back to this whole programming of what we think we need. That's the number one tip. The number 2 tip is have great photos and #3. The tip is tell a story about who you are and when you're writing that story. This is not to give away what I do, but in that story incorporate what that man who you're seeking or woman. Who they are. So you read. This story and they say wow. That's me. I can see myself with this woman or man. Yeah, I see myself with this person rather than the mundane of I like to go out to eat. I like going to movies. I like to chill on Netflix. I like sports. I like going hiking. Cycling, biking OK, well everyone likes that be the woman who stands out you know that I mean mine is really silly. Mine is I spend my days unsubscribing from unwanted emails. Removing the tags that are on furniture accessories. And what I'm feeling especially frisky, I'll go to Taco Bell and rearrange the assortment of condiments just for fun.
THERESA: Yes, but it keeps you, like you said, different and fun and in a positive light.
LORI: Yes, so this guy sees, well that woman's either crazy or quirky.
THERESA: So another question we got was what makes a good first date?
LORI: I'm going to say an equal back and forth in a conversation. You know, a major complaint with women is, and men, I'll say this, is that people use the time on a first date to recite a monologue. Don't do that. Ask a question. Wait for an answer. It should be a back and forth. It should spark interest. It should spark conversation. You should keep it fun. You should keep it light. Just look at it as a discovery period. Keep it open and loose and flowing, and without pretense or without preconceived notion or without expectation. And so I always advise people to do something outdoors on their first date, because you're not sitting across from a table from someone who, hate to say it, many times looks nothing like their picture. It should be fun, light, short, casual, simple, no meals, no heavy duty things. It just should not be that. It should be short, sweet. Fun, flirty, good conversation back and forth, that's it.
THERESA: What questions would you recommend asking in those early stages of dating?
LORI: There's an article that the New York Times published years ago called 33 or 35 questions that lead to love. The people who are listening can just Google that, but it's really good. So the questions that I advise people to ask are questions that deserve an answer, not like what is your favorite. Food OK, you're going to say, you know, linguine Al Pesto. That is my favorite food. OK, where's that going? Or tell me about your family. Well I have two sisters and a brother. And both my parents are deceased. OK, that leads us nowhere. So the way that the questions should be posed are: I'd love to hear about your family. Can you share with me one of your most precious moments? Of your childhood. Another question could be what are you most proud of? Tell me about someone who influenced your life and how did they do so, because that creates an open space for the person to say wow, I really gotta think about that one you know, yeah, I think my father was my biggest influence and then I have the opportunity to say, tell me more and it creates a story. Exactly exactly tell me more. I mean, I have a question which is if your house were on fire and this takes thought because I already know the question, but if your House was on fire and aside from taking your children and your dog or your cat and your laptop, what would you grab first? What is that one precious thing? To you that means so much. And what is the sign? Significance of it, and that isn't fun and flirty, but it leads to an opening of conversation and it leads to them saying back to. You wow, you know let. Let me think about that for a minute. What about you? What would you take that gives them time to think about theirs? So it's questions that are not especially heavy. My favorite one is tell me about the happiest day of your life. Other than the day that you're. Kids report, and that puts someone in. A really great mood. They're telling you about the happiest day of their life, but all those questions also make a person feel like you really care about knowing more about them genuinely would like to get to know them better and hear their life experiences. And here's a warning label here. I've gone out on dates where I've asked those questions and the guy has said to me. You know, Lori I, I really think you're terrific, but. You're really too deep for me. OK, thank you. No need for self selection here, we're. Already you know you're not my guy because my guy. To be interested in those questions, and it isn't a place where I would go. God, I shouldn't have asked those questions. I think, wow, that's great. That's really great that. You pulled yourself out of the hat here and I'm not gonna waste my time investing anymore. And you were thinking about you. I'll move on to. The next yeah.
THERESA: There's so much more that goes into your work with people than just dating.
LORI: The last two weeks, the clients that I've been working with have been either like, saying, Oh my. God, how did you do that? I never thought of that or they've been crying. Which is good. Because crying is growth, you know I have some young men who are hiring me, which is great because they don't know how to be in relationships. They want to learn how to date and people come in with one agenda. That what do I need to do? Let's rephrase. What work do you need to do on you to get you to a place where you will find it? For men creates this whole opportunity for them to say God. I've just been doing the same. And over and over and over again. No wonder these relationships are not working out for me. So the number one thing is that women who are strong and bold and successful they don't leave this armor at the door. They don't use their feminine energy.
THERESA: I love so much working with new Mamas. This is a big one that comes up. Is figuring out how to create a balance between the masculine and the feminine energies that we all possess. We are rewarded for decades as we establish ourselves in society as we establish our careers that we're rewarded for productivity and big time independence versus the nurturing and the quiet.
LORI: And the support and the asking for help. I mean, this is one of those things that constantly keeps coming up. You know we're trained now. I don't need to ask anyone for help because I'm strong and I'm independent. We don't want to appear weak, but if we don't create a space for men to join us or to complement our lives or to bring their masculine energy, they're gonna find someone who will, you know? And I don't mean to go back to the 1950s of having a martini ready when the guy walks through the door. What I mean is, is creating that space of saying you know I'd love your opinion on this. I think even just asking for help. That's an exercise that a lot of my clients I teach them. This is not even on a date, just start practicing. It's like muscle memory. When you're working, you know when you're working out just start getting into asking for help, complimenting, acknowledging a man and his tenderness and his kindness. Because that goes a really long way. A topic that has been on repeat. It is vulnerability Mm-hmm and how a lot of us men and women have stigmatized being vulnerable Mm-hmm when really when you get comfortable in vulnerability, it really enriches and builds trust and a much deeper connection. I think that's another side of this.
Yes, and that's why we all want to get there. You know, there's nothing better than being cozy with someone and just being yourself and just being just being just being in the same room, knowing that everything is good in the world. That's the best part.
And if vulnerability can lead to that authenticity, Mm-hmm how much more meaningful our relationships would be with each other, yes, but we're so afraid of that. Well, guess what? We've been hurt before and if I'm vulnerable, you know.
But there's a part of letting go of the ego.
THERESA: In that search of something bigger, what do you do for yourself, Lori, to continue to engage and commit to each client at this level? What do you do for yourself to stay grounded in your own life?
LORI: Hmm, well I don't overbook myself. That's really important. And I also have boundaries. I do a lot of reading. I listen to a lot of podcasts. I try to keep very fresh on topics. Psychology mainly not data. Dating because dating is pretty much a new thing. It's only like 100 years old. 100 years ago women were promised to men, so it's a relatively new thing. But where I live now, I live right by the Atlantic Ocean. I grew up in Southern California by the ocean, and she speaks to me every morning. I walk along the beach and every morning I walk my dogs. And to see the joy in my dogs running, I have almost a 15 year old dog who is running like she's a puppy. And that brings me joy. I speak out loud when I am at the ocean. I speak my gratitude. I just speak. Thank you for bringing me here. Thank you for giving me the courage to see you and be with you and be around you. I didn't know one person here. I just blindly said I'm going. I'm selling my stuff I'm moving, I'm going there. I hike I love being in Mother Nature. She soothes my soul so that is what that is. My balm. Friendships are my balm. My girlfriend tribe is my support system and my guy friend tribe I love.
Hearing the way each person I talked to defines self-care Mm-hmm it's different for everybody. You know, we've moved beyond seeing self-care as getting a quick Mani pedi. It's that walk in nature that really grounds me Mm-hmm. It's that making sure that I have a phone call or a coffee date with my best girlfriend. Taking time to realize what are those things that surround us in our environment that bring us.
I mean, my dogs are a big part of my life too. I mean they keep me active but they Get Me Out of nature. Never knows where. Those connections are going to go, it's you know. The domino effect.
THERESA: I am a lifelong lover of connecting those dots. It's been so fun, Lori. Talk about making connections. I've so enjoyed having this time with you.
LORI: Well, I am going to invite you here to Maine whenever you want to come. Thank you, Theresa.
JEN: Thanks for joining us today. We invite you to hit subscribe and to keep coming back each week for a new empowering conversation. We look forward to seeing you at our website where you'll find our newsletter, events, dates, and other amazing resources. Visit interwoven.com that's INTERWOVXN.com to Sign up today. This shows copyright. This January of 2023, we want to thank in Context, Inc. Digital marketing agency and the sugar Maple bar for their support this season, as well as our producers Teresa Kopak, Rebecca Jankowski and Jen Gilmour. All original music was created and performed by Janet Ransdell and Susie Muehlbauer.